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Best Of

October 27, 2025 by Boston Southie

At-a-Glance

  • Neighborhoods covered: Downtown, Theater District, Seaport, Fenway •
  • MBTA notes: Weekend subways & key buses run ~1 hr later (to ~2 a.m.) on Fri/Sat; select promo weekends free after 9 p.m. •
  • Time/budget: Mostly 9 p.m.–2 a.m.; $–$$$ with VIP add-ons •

Updated: September 2025


The Liberty Hotel — “Beetlejuice” Halloween Party

Happy Family in Halloween Costumes Celebrating Event in Boston

Boston’s most cinematic Halloween blowout takes over the Liberty’s atrium with DJs, dance performances, photo ops, and 600 costumed revelers. Expect high-production lighting and themed sets; VIP tables put you above the action on the catwalk. Bars stay card-only, and the crowd leans into full-costume photo energy. Buy early—the mezzanine VIPs sell out fastest.

  • Price: GA $95 (early) | Last Minute $110 | Catwalk VIP (8 ppl) $1,500 | Lobby VIP (10 ppl) $1,850
  • When: Sat 10/26, 9 p.m.–close
  • Tickets: libertyhotel.com
  • MBTA/Parking: Red Line Charles/MGH; garages nearby
  • Link: libertyhotel.com

Royale — The Boulet Brothers Halloween House Party (18+)

The Theater District pulls in Boston’s largest Halloween crowd at Royale, where the Boulet Brothers bring their drag-horror spectacle. Stage-front tickets put you in the splash zone; GA balconies work for people-watching with room to breathe. Expect pounding DJs, a nonstop light show, and a line outside if you don’t buy in advance.

  • Price: Stage Front $64 | GA Balcony $39
  • When: Fri 10/31, 9 p.m.–2 a.m.
  • Tickets: royaleboston.com
  • MBTA/Parking: Boylston / Chinatown stops; Tremont garages
  • Link: royaleboston.com

House of Blues — THRICE Halloween Night

Fenway swaps dance beats for guitars with THRICE headlining Halloween at House of Blues. GA floor packs in early for the pit; balcony seats keep you above the crush with a full view. It’s one of the rare ticketed rock anchors on Halloween night, and resale prices usually creep up fast.
Price: GA Floor $50+ | Reserved Balcony $70+
When: Fri 10/31 (doors ~6:30 p.m.)
Tickets: houseofblues.com/boston
MBTA/Parking: Green Line Kenmore; Lansdowne garages
Link: houseofblues.com/boston


The Grand — Seaport Halloween Weekend

Women in Cat Ears Enjoying Halloween Party at Seaport Megaclub

Seaport’s glossy megaclub leans hard into spectacle, with big-name DJs, bottle parades, and costumes turned into full runway moments. GA tickets get you in the crush; table buys anchor you at the rail with service. Lines back up quick after 11, so presale is the move.

  • Price: GA ~$20+ | VIP Tables $1,000+
  • When: Fri & Sat of Halloween weekend, 10 p.m.–2 a.m.
  • Tickets: thegrandboston.com
  • MBTA/Parking: Silver Line Courthouse; One Seaport Garage
  • Link: thegrandboston.com

Boston Halloween Party Cruises

Harbor cruises bring club energy onto the water with DJs, multiple decks, and a skyline backdrop. Costumes go big, boarding is strict, and once the boat leaves you’re locked in until docking. Tickets climb close to sail date, so lock GA early if you’re set on a theme night.

  • Price: GA ~$45–$65 | VIP Deck Packages vary
  • When: Multiple nights incl. Fri 10/31 (6–9:30 p.m. sailings)
  • Tickets: Eventbrite organizer pages (Bay State Cruise Company piers)
  • MBTA/Parking: Silver Line Courthouse; Seaport garages
  • Link: baystatecruisecompany.com / Eventbrite

Official Halloween Bar Crawls

Downtown crawls keep Halloween loose with multi-bar wristbands, drink specials, and after-parties stacked into one ticket. Costumes range from casual to elaborate, and each organizer posts its own start points. Buy online for the best price—tier jumps add up if you wait.

  • Price: GA ~$16–$25 (tiered)
  • When: Sat 10/25, Fri 10/31, Sat 11/1
  • Tickets: barcrawllive.com | pubcrawls.com
  • MBTA/Parking: Green/Orange/Blue hubs; walkable between venues
  • Link: barcrawllive.com / pubcrawls.com

Free Traditions (Bonus Picks)

Group of Friends Enjoying Halloween Party in Boston

Fall-o-Ween on the Boston Common (Frog Pond)
The city drops a Halloween block right in the middle of the Common, with music, costumed crowds, and food vendors circling Frog Pond. It’s the easiest way to see thousands of costumes without paying a cover, and the energy ramps as night falls. Think of it as the warm-up before you head downtown for the ticketed parties.

  • Price: Free
  • When: Thu 10/17, evening
  • Tickets: None required
  • MBTA/Parking: Red/Green Line Park Street
  • Link: boston.gov

Spooky Streets (City of Boston Block Parties)
City-sanctioned block parties run across Boston from October 17 through November 2, with closed streets, music, and bars spilling onto the sidewalks. Each neighborhood does it differently—some lean DJ-heavy, others add food trucks and pop-up beer gardens—but all keep it free to join. Drop in, grab a drink from a nearby bar, and let the costumed crowd carry the night.

  • Price: Free
  • When: Oct 17–Nov 2, evenings vary
  • Tickets: None required
  • MBTA/Parking: Neighborhood-dependent; most routes hit MBTA core stops
  • Link: boston.gov

Ticket & Transit Tips

  • On-sale windows: Most clubs/cruises release tickets 3–6 weeks out; each tier sells up.
  • What’s included: GA = entry; VIP adds table service, expedited lines, better placement. 
  • MBTA: Subways run until ~2 a.m. Fri/Sat; check if your weekend qualifies for the free-after-9 promo.

Filed Under: Upcoming Events

August 27, 2025 by Boston Southie

Looking to make the most of Boston’s crisp fall weekends? From food fests to cultural parades and harvest fairs, here’s your weekend-by-weekend guide to the best fall events running from September through November.


Fall festivals

At-a-Glance

  • Coverage: Boston-wide
  • MBTA notes: Most events accessible by Red/Green/Orange Lines
  • Budget: Mix of free & ticketed events
  • Updated: August 2025

Weekend-by-Weekend Picks

September 6–7: Boston Arts Festival (Christopher Columbus Park, North End)

Boston kicks off fall with a juried showcase of visual and performing arts. Expect local painters, sculptors, and photographers alongside live music on the waterfront. Great for browsing and picking up affordable art.

  • Price: Free
  • MBTA/Parking: Aquarium (Blue Line) or Haymarket (Green/Orange)
  • Accessibility: Flat park paths, stroller/dog friendly
  • Link: bostonartsfestival.org

September 20–21: South Boston Street Festival

This long-running Southie tradition transforms East Broadway into a corridor of music, food stalls, and local vendors. A family-friendly day with live bands and community flavor.

  • Price: Free
  • MBTA/Parking: Broadway (Red Line)
  • Accessibility: Street-level, stroller friendly, some side-street bathrooms
  • Link: sbndc.org/streetfest

September 27–28: Oktoberfest at Harpoon Brewery (Seaport)

Boston Oktoberfest

Harpoon’s annual Oktoberfest delivers craft beer, live oompah music, and food trucks. It’s crowded but festive—grab a pretzel and join the stein-hoisting contest.

  • Price: $$ (~$25 entry + food/drink)
  • MBTA/Parking: Silver Line Courthouse
  • Accessibility: Large tent setup, portable restrooms, not stroller ideal
  • Link: harpoonbrewery.com

October 4–5: Cambridge Oktoberfest & HONK! Parade (Harvard Square)

A mix of global street bands, activist energy, and Oktoberfest food stalls. The HONK! Parade is loud, colorful, and one of Boston’s most spirited events.

  • Price: Free
  • MBTA/Parking: Harvard (Red Line)
  • Accessibility: Street event, stroller friendly, crowds dense
  • Link: harvardsquare.com

October 11–12: Indigenous Peoples Day Newton Powwow (Newton Centre Green)

Celebrate Indigenous music, dance, and culture with craft vendors and food. A quieter, family-friendly festival honoring Native traditions.

  • Price: Free
  • MBTA/Parking: Newton Centre (Green Line D)
  • Accessibility: Grass/lawn surface, portable toilets, stroller accessible
  • Link: indigenouspeoplesdayma.org

October 18–19: Head of the Charles Regatta (Cambridge/Boston)

The world’s largest 2-day rowing event brings elite crews and huge crowds along the Charles River. Best views near Eliot Bridge or Weeks Footbridge.

  • Price: Free
  • MBTA/Parking: Harvard/Central (Red Line)
  • Accessibility: Riverbank paths, portable restrooms, not stroller ideal
  • Link: hocr.org

October 25–26: Boston Veg Food Fest (Reggie Lewis Center, Roxbury)

One of the longest-running plant-based food festivals in the U.S., with tastings, cooking demos, and vendors. A must for veg-curious eaters.

  • Price: Free
  • MBTA/Parking: Roxbury Crossing (Orange Line)
  • Accessibility: Indoor event, wheelchair/stroller accessible bathrooms
  • Link: bostonveg.org

November 1: Día de los Muertos Festival (East Boston)

Community altars, dance, and food celebrate Mexican Day of the Dead traditions. Expect marigolds, papel picado, and family-friendly art activities.

  • Price: Free
  • MBTA/Parking: Maverick (Blue Line)
  • Accessibility: Indoor/outdoor mix, stroller accessible
  • Link: meetboston.com

November 9: Boston Comedy Festival (Somerville)

A week-long series, but the opening weekend packs headliner shows and competitions. A lively pick for a colder November night.

  • Price: $$–$$$
  • MBTA/Parking: Davis (Red Line)
  • Accessibility: Theater seating, wheelchair accessible
  • Link: bostoncomedyfest.com

November 16: Boston International Fine Art Show (Cyclorama, South End)

Boston’s only curated fine art fair, featuring galleries from across the U.S. Gives everyone a chance to browse museum-quality works in a historic setting.

  • Price: $$ (~$15 entry)
  • MBTA/Parking: Back Bay (Orange Line) or Arlington (Green Line)
  • Accessibility: Indoor venue, wheelchair accessible
  • Link: fineartboston.com

November 23–24: Boston Christmas Festival (Seaport World Trade Center)

Boston Christmas Fest

Yes, Christmas comes early—this massive craft show features 300+ artisans, specialty foods, and holiday décor. A festive finale to the fall season.

  • Price: $$ (~$20 entry)
  • MBTA/Parking: Silver Line World Trade Center
  • Accessibility: Indoor venue, wheelchair accessible, stroller friendly
  • Link: bostonchristmasfestival.com

Recommendations

If you’re new to Boston, prioritize Head of the Charles for sheer spectacle, and HONK! Parade for street-level joy. For food lovers, Harpoon Oktoberfest and Boston Veg Food Fest bookend the season perfectly. And if you’re looking to shop early, the Christmas Festival is unmatched.

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Filed Under: Best Of, Family, Outdoors, Seasonal, Seasonal, Upcoming Events

August 27, 2025 by Boston Southie

Fall in Boston means crisp air, changing leaves, and plenty of ways to fill a day without leaving the city. Here’s a mix of outdoors, indoors, and seasonal events—all MBTA-friendly—for when you’ve got a free day to make the most of September and October.


Boston Fall

At-a-Glance

  • Neighborhoods: Citywide (North End, South End, Fenway, JP, Dorchester, Cambridge, more)
  • MBTA stops: Red, Green, Orange, Blue, Silver lines covered
  • Mix: Outdoors walks • Festivals & events • Indoor culture & food
  • Best timing: Early fall weekends, afternoons for foliage
  • Price tiers: Free, $, $$
  • Updated: August 2025

Arnold Arboretum Foliage Walk — Jamaica Plain

The Arboretum turns into a fall postcard by late September, with maples and oaks lighting up in red and gold. Paths range from paved to dirt, making it easy to tailor a short stroll or a longer loop. Bathrooms sit at the Hunnewell entrance, and the Orange Line to Forest Hills puts you a ten-minute walk away. Aim for the morning if you want quieter paths.

  • Cost: Free
  • MBTA/Parking: Forest Hills (Orange Line); limited street parking
  • Accessibility: Paved sections stroller- and wheelchair-friendly
  • Link: arboretum.harvard.edu

SoWa Open Market — South End

Every Sunday in fall, SoWa mixes art vendors, vintage finds, and plenty of food trucks. The atmosphere leans festive without being overwhelming, and the open-air layout makes it a good way to spend a few hours. Grab lunch from a rotating set of trucks, then browse local makers.

  • Cost: Free entry; food and goods $–$$
  • MBTA/Parking: Broadway or Back Bay (Red/Orange Line)
  • Accessibility: Fully paved, open layout
  • Link: sowaboston.com

MFA Fall Exhibits — Fenway

The Museum of Fine Arts shifts into fall with big-ticket exhibits and reliable permanent collections. It’s an easy pivot if the weather turns, and you can time your visit for a weekday afternoon when galleries are calmer. Free entry on Wednesday evenings makes it budget-friendly.

  • Cost: $$ (~$27 general admission; free Wed 5–9)
  • MBTA/Parking: Museum of Fine Arts stop (Green Line E)
  • Accessibility: Fully ADA accessible
  • Link: mfa.org

Head of the Charles Regatta — Cambridge

Late October brings the Head of the Charles, a weekend-long rowing event that pulls spectators along both sides of the river. It’s busy but fun—plan to stand or bring a folding chair, and layer up against the breeze. The view from Weeks Footbridge gives you one of the best vantage points.

  • Cost: Free
  • MBTA/Parking: Harvard or Central (Red Line)
  • Accessibility: Uneven grass along banks; paved bridges
  • Link: hocr.org

North End Boston

Greenway Carousel & Farmers Market — North End

  • Why: Seasonal produce and a whimsical carousel in the same stop. Families can snack, spin, and shop without leaving the park.
  • Cost: Free entry; market goods $
  • When: Fridays and Saturdays
  • MBTA: Haymarket (Green/Orange)
  • Accessibility: Paved, stroller-friendly
  • Link: rosekennedygreenway.org

Castle Island Stroll — South Boston

  • Why: Breezy walk around Fort Independence with harbor views. It’s a neighborhood staple and always feels calmer in the shoulder season.
  • Cost: Free
  • When: Mornings for fewer crowds
  • MBTA: Broadway (Red Line) + #9 bus
  • Accessibility: Paved, stroller- and wheelchair-friendly
  • Link: mass.gov/locations/

Boston Book Festival — Back Bay

  • Why: Author talks, book browsing, and family activities each October. The energy in Copley Square makes it feel like a citywide book club.
  • Cost: Free
  • When: October weekend dates
  • MBTA: Copley (Green Line)
  • Accessibility: Outdoor tents + library venues
  • Link: bostonbookfest.org

Sam Adams Taproom Fall Flights — Downtown

  • Why: Try seasonal brews on the rooftop deck with skyline views. The pumpkin and Oktoberfest pours are local favorites.
  • Cost: $$ (~$12–15 for flight)
  • When: Afternoons; weekends fill up
  • MBTA: Downtown Crossing (Red/Orange)
  • Accessibility: Elevator access
  • Link: samueladams.com

Eastie Pumpkin Mural Walk — East Boston

  • Why: Local artists add seasonal murals near Maverick Square. It’s a colorful photo stop that changes every year.
  • Cost: Free
  • When: September–October
  • MBTA: Maverick (Blue Line)
  • Accessibility: Paved sidewalks
  • Link: eastbostonmainstreets.org

Fenway Park Tour — Fenway

  • Why: Off-season tours show the park’s history and Green Monster views. Guides mix fun trivia with serious baseball lore.
  • Cost: $ (~$25)
  • When: Daily tours, check schedule
  • MBTA: Kenmore (Green Line)
  • Accessibility: Some stairs; call ahead for ADA routes
  • Link: mlb.com/redsox/ballpark/tours

ICA Watershed — East Boston

  • Why: Seasonal art space in a converted shipyard; open through fall. The ferry ride adds a bonus harbor view.
  • Cost: Free with ICA admission
  • When: Weekends
  • MBTA: Maverick (Blue Line) + ICA ferry
  • Accessibility: Fully ADA accessible
  • Link: icaboston.org

JP Loring-Greenough House Lawn — Jamaica Plain

  • Why: Community lawn events, from concerts to cider tastings. The historic setting adds charm to casual gatherings.
  • Cost: Free–$
  • When: Fall weekends
  • MBTA: Stony Brook (Orange Line)
  • Accessibility: Lawn surface, uneven in spots
  • Link: loring-greenough.org
Dorechester Boston

Franklin Park Zoo Fall Days — Dorchester

  • Why: Cooler weather makes animals more active; kids love the seasonal decor. The giraffe and lion enclosures draw steady crowds.
  • Cost: $$ (~$24 adult, $17 child)
  • When: Weekends in September–October
  • MBTA: Forest Hills (Orange Line) + bus
  • Accessibility: Paved paths, stroller-friendly
  • Link: franklinparkzoo.org

Trillium Beer Garden — Greenway

  • Why: Outdoor beer garden with local brews and city views. Groups spread out easily, and the vibe feels relaxed even downtown.
  • Cost: $$ (~$8–10 per pour)
  • When: Early evenings
  • MBTA: South Station (Red Line)
  • Accessibility: Paved, open-air
  • Link: trilliumbrewing.com

Old North Church Lantern Tour — North End

  • Why: Evening tours add atmosphere to a classic site. The lantern-lit setting feels especially right in crisp fall air.
  • Cost: $ (~$10–15)
  • When: September–October evenings
  • MBTA: Haymarket (Green/Orange)
  • Accessibility: Historic building, uneven floors
  • Link: oldnorth.com

Filed Under: Best Of, Family, Outdoors, Seasonal, Seasonal, Upcoming Events

August 27, 2025 by Boston Southie

Looking for what’s worth your time this week? Here’s a neighborhood-organized list of 25 things to do across Boston — mixing late-summer energy with early-fall musts, plus why locals and visitors love them.


Boston city view

At a Glance

  • Neighborhoods covered: Back Bay, Fenway, Seaport, South End, JP, Charlestown, North End, Dorchester
  • MBTA notes: All picks within 10-min walk of Red, Orange, or Green Line stops
  • Time/budget filters: Free–$$$ mix; clustered so you can stack 2–3 in a day
  • Updated: August 2025

Recommendations

Back Bay & Fenway

1. Fenway Park Tour — Fenway

  • Why: Boston’s baseball cathedral still draws fans long after the season ends. Visitors say the behind-the-scenes peek into dugouts and the press box makes it unforgettable.
  • Do: Book a guided tour; catch skyline views from the bleachers.
  • Price: $$ (~$27 pp).
  • When: Morning slots lighter.
  • MBTA/Parking: Green Line Kenmore.
  • Accessibility: Elevators; step-free seating areas.


Link

2. Isabella Stewart Gardner Museum — Fenway

  • Why: The Venetian-style courtyard and legendary art heist intrigue visitors. Guests often say the mix of lush gardens and rare pieces feels like stepping into another world.
  • Do: Spot the empty frames from the infamous heist.
  • Price: $$ (~$20 pp).
  • When: Weekday mornings = calmer.
  • MBTA: Green Line Museum stop.
  • Accessibility: Elevators + accessible bathrooms.


Link

3. Commonwealth Ave Mall Walk — Back Bay

  • Why: Locals love this leafy stretch for dog-walking and first hints of fall color. It feels like a city escape without leaving downtown.
  • Do: Walk from Kenmore to Public Garden.
  • Price: Free.
  • When: Golden hour.
  • MBTA: Green Line Hynes.
  • Accessibility: Paved + curb cuts.


Link


Seaport & South End

Seaport Boston

4. ICA Boston — Seaport

  • Why: Contemporary art with unforgettable harbor views. Visitors rave about the rooftop deck and how exhibits keep changing so it’s never the same visit twice.
  • Do: Start with the fourth-floor deck.
  • Price: $$ (~$20 pp; free Thursdays 5–9).
  • When: Late afternoons thin out.
  • MBTA: Silver Line Courthouse.
  • Accessibility: Elevators; wheelchair seating in theater.


Link

5. Seaport Beer Garden Crawl — Seaport

  • Why: Patio-hopping here makes you feel like you’re on vacation without leaving Boston. Locals love the casual vibe and harbor breeze.
  • Do: Harpoon → Cisco → Trillium patios.
  • Price: $$ (~$8–10 per pour).
  • When: Weekdays after work.
  • MBTA: Silver Line World Trade.
  • Accessibility: Paved surfaces; bathrooms vary.


Link

6. SoWa Open Market — South End

  • Why: A weekend tradition where Boston creatives show off art, vintage, and food. Families and young crowds alike enjoy wandering the vendor stalls.
  • Do: Snack + shop from 200 vendors.
  • Price: Free entry; $–$$$ shopping.
  • When: Sundays 11–4.
  • MBTA: Silver Line Broadway.
  • Accessibility: Paved lots; porta-potties onsite.


Link


North End & Downtown

7. North End Feast Weekends — North End

  • Why: For decades, these Italian street festivals have been the city’s unofficial block parties. Crowds come for live music, parades, and endless cannoli.
  • Do: Try pastries from Mike’s vs. Modern.
  • Price: $ (~$8–12 pp).
  • When: Fri–Sun evenings in August/Sept.
  • MBTA: Orange Line Haymarket.
  • Accessibility: Crowded sidewalks; limited seating.


Link

8. Old North Church — North End

  • Why: Famous for “One if by land, two if by sea,” the church offers a tangible link to America’s founding. Visitors enjoy the historic pew boxes and bell-ringing demos.
  • Do: Climb up for bell-ringing demos.
  • Price: $ (~$10 pp).
  • When: Early AM before school tours.
  • MBTA: Orange Line Haymarket.
  • Accessibility: Narrow stairs; some areas limited.

Link

9. Rose Kennedy Greenway Carousel — Downtown

  • Why: Families love the hand-carved animals, designed to reflect New England species. It’s a cheerful stop paired with food trucks and Greenway lawn time.
  • Do: Pair with a Greenway food truck.
  • Price: $ (~$4/ride).
  • When: Afternoons best.
  • MBTA: Orange Line Haymarket.
  • Accessibility: Step-free boarding.

Link


Jamaica Plain & Dorchester

10. Arnold Arboretum — JP

  • Why: Nature lovers come for seasonal colors, and locals swear by the skyline view at Peters Hill. It’s one of Boston’s top free escapes.
  • Do: Climb Peters Hill for skyline.
  • Price: Free.
  • When: Mornings before crowds.
  • MBTA: Orange Line Forest Hills.
  • Accessibility: Paved + gravel; bathrooms near main gate.

Link

11. Sam Adams Brewery Tours — JP

  • Why: A classic stop for both tourists and locals who want small-batch beers in the city where it all started. Fans love seasonal releases and chill beer garden vibes.
  • Do: Try fall brews + beer garden.
  • Price: $ (~$10 pp tastings).
  • When: Weekdays <4 p.m. best.
  • MBTA: Orange Line Stony Brook.
  • Accessibility: Restrooms; some uneven surfaces.

Link

12. Franklin Park Zoo — Dorchester

  • Why: Families like how big the grounds are, giving kids space to roam. Cooler weather perks up the giraffes and lions, making this season a hit.
  • Do: Giraffes + playground.
  • Price: $$ (~$24 adult).
  • When: Early AM.
  • MBTA: Orange Line Forest Hills → bus.
  • Accessibility: Paved + stroller rental.

Link


Charlestown & Waterfront

Charlestown Boston, MA

13. Bunker Hill Monument — Charlestown

  • Why: Free climb, sweeping views, and history that school groups and locals alike still find moving. It’s a workout with bragging rights.
  • Do: 294 steps; bring water.
  • Price: Free.
  • When: Weekday mornings.
  • MBTA: Orange Line Community College.
  • Accessibility: Climb only; grounds step-free.

Link

14. USS Constitution — Charlestown Navy Yard

  • Why: “Old Ironsides” is America’s ship — families say kids love running across the decks and seeing the cannons. Locals appreciate it’s still afloat.
  • Do: Explore decks + museum.
  • Price: Free (donation suggested).
  • When: Early PM.
  • MBTA: Orange Line North Station.
  • Accessibility: Ramps to main deck; museum accessible.

Link

15. Harborwalk Sunset Loop — Waterfront

  • Why: Couples, joggers, and photographers all rave about the evening glow here. It’s one of the city’s simplest and most rewarding walks.
  • Do: Walk from Fan Pier → Seaport Green.
  • Price: Free.
  • When: 6–8 p.m.
  • MBTA: Silver Line Courthouse.
  • Accessibility: Flat + stroller-friendly.

Link


Extra Picks (Seasonal + Food)

16. MFA Late Nights — Fenway

  • Why: Once a month, the Museum of Fine Arts keeps doors open late with live music, cocktails, and gallery access. Locals treat it as a classy night out that still feels affordable.
  • Do: Explore after dark and grab a drink in the atrium.
  • Price: $$ (~$25 pp; bar extras).
  • When: Monthly; check schedule.
  • MBTA: Green Line Museum stop.
  • Accessibility: Elevators + wheelchair seating.

Link

17. Charles River Kayaks — Allston

  • Why: A favorite late-summer activity where you can paddle past skyline views and college crews. Visitors love the calm stretch between Harvard and BU.
  • Do: Rent a single or double kayak.
  • Price: $$ (~$22/hr).
  • When: Afternoons best.
  • MBTA: Red Line Harvard or Green Line BU.
  • Accessibility: Docks have assisted launches.

Link

18. Tatte Bakery — South End

  • Why: Instagram-famous pastries and Mediterranean plates. Locals call it their go-to brunch stop before SoWa or a long city walk.
  • Do: Order the shakshuka or pistachio croissant.
  • Price: $–$$ (~$15–20 pp).
  • When: Weekday mornings lighter.
  • MBTA: Silver Line Broadway.
  • Accessibility: Street-level entrance; bathrooms on main floor.

Link

19. Newbury Street Shopping — Back Bay

  • Why: Boston’s most stylish stretch mixes big brands with indie boutiques. People-watchers and bargain-hunters both find something.
  • Do: Stroll from Mass Ave down to Public Garden.
  • Price: Free to stroll; $$$ to shop.
  • When: Afternoons + weekends busiest.
  • MBTA: Green Line Hynes.
  • Accessibility: Paved sidewalks, curb cuts.

Link

20. Harpoon Breweryfest — Seaport

  • Why: Seasonal beer festivals bring live music, pretzels, and fall brews. Locals treat it like the unofficial start to autumn.
  • Do: Sample limited-release Oktoberfest beers.
  • Price: $$ (~$30 entry + drinks).
  • When: September weekends.
  • MBTA: Silver Line World Trade.
  • Accessibility: Warehouse setup, step-free.

Link

21. Castle Island Walk + Sully’s — South Boston

  • Why: Families and runners crowd the loop for breezy harbor views, then reward themselves with fried clams or hot dogs from Sullivan’s.
  • Do: Walk the 2-mile loop, eat after.
  • Price: Free walk; $ snacks.
  • When: Afternoons cooler.
  • MBTA: Red Line Broadway + bus.
  • Accessibility: Flat paved loop; restrooms available.

Link

22. Black Heritage Trail — Beacon Hill

  • Why: A self-guided walk exploring 19th-century Black history sites. Residents say it adds depth to the Freedom Trail and highlights overlooked stories.
  • Do: Start at the Museum of African American History.
  • Price: Free.
  • When: Morning or early afternoon.
  • MBTA: Red Line Charles/MGH.
  • Accessibility: Brick sidewalks; some uneven terrain.

Link

23. Boston Public Market — Downtown

  • Why: Year-round market where locals stock up on cider donuts, produce, and handmade goods. Visitors love sampling small-batch treats.
  • Do: Try Union Square Donuts + Red Apple Farm stand.
  • Price: $–$$ (~$15–25 pp).
  • When: Weekends busiest; weekdays calmer.
  • MBTA: Orange Line Haymarket.
  • Accessibility: Indoor, step-free.

Link

24. Coolidge Corner Theater — Brookline

  • Why: Indie films, cult classics, and midnight specials. Locals rave about the art deco vibe and rare screenings.
  • Do: Catch a 35mm or midnight showing.
  • Price: $ (~$15 ticket).
  • When: Evenings.
  • MBTA: Green Line Coolidge Corner.
  • Accessibility: Step-free entrance; accessible seating.

Link

25. Lawn on D — Seaport

  • Why: The glowing swings and outdoor games make this a summer-fall hangout. Families, young professionals, and visitors all crowd in for live music and beer garden vibes.
  • Do: Swing, play, grab food truck eats.
  • Price: Free entry; $–$$ for snacks.
  • When: Evenings + weekends busiest.
  • MBTA: Silver Line World Trade.
  • Accessibility: Paved lot; portable restrooms.

Link

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Filed Under: Best Of, Lifestyle

August 27, 2025 by Boston Southie

For those who wake up hungry, Boston offers plenty of breakfast spots that open before the city really gets moving. Here’s where to grab eggs, bagels, or pancakes by neighborhood.


At-a-Glance

  • Neighborhoods: Fenway/Kenmore, South End, Back Bay, Dorchester, East Boston
  • MBTA stops: Kenmore, Back Bay, Broadway, Fields Corner, Maverick
  • Price tiers: $–$$ (most breakfasts $8–$18)
  • Wait/Resy notes: Walk-in friendly; weekends busier
  • Dietary tags: Vegetarian, vegan, gluten-free options available
  • Hours: Many open 6:30–7:00 a.m.

Fenway/Kenmore

Fenway Boston

Tatte Bakery & Café — Fenway

Tatte is one of Boston’s earliest-opening cafés, with doors open by 7 a.m. Their shakshuka, almond croissants, and loaded breakfast sandwiches bring in students, commuters, and hospital staff from Longwood. Seating fills quickly, but takeout is fast and consistent. Their vegan and gluten-free options are clear on the menu, making it easy to find something for any diet.

  • Price: $–$$ (~$6–$15)
  • MBTA/Parking: Kenmore (Green Line)
  • Accessibility: Wheelchair accessible, counter ordering
  • Link: tattebakery.com

Thornton’s Fenway Grille — Fenway

Classic diner plates with portions that fuel an entire day. Pancakes arrive fluffy and huge, while the omelets pack in the fillings. It’s a locals’ spot before 9 a.m., with quieter seating than most Fenway cafés. If you want a no-nonsense plate and hot coffee before catching the T, this is the move.

  • Price: $ (~$8–$14)
  • MBTA/Parking: Symphony (Green Line) or Hynes
  • Accessibility: Small step at entry, booth seating
  • Link: thorntonsfenwaygrille.com

South End

South End Boston

Mike’s City Diner — South End

Mike’s opens at 6 a.m. and serves hearty breakfasts that lean old-school—think corned beef hash, thick-cut bacon, and home fries piled high. It’s counter seating and big mugs of coffee, with regulars mixing with visitors on medical shifts. The vibe is friendly and brisk, and plates hit the table fast. Vegan choices are limited, but vegetarians can count on eggs, toast, and sides.

  • Price: $ (~$10–$16)
  • MBTA/Parking: Back Bay (Orange Line)
  • Accessibility: Narrow aisles, no reservations
  • Link: mikescitydiner.com

South End Buttery — South End

Known for breakfast sandwiches on house-baked biscuits and scones, South End Buttery is a cozy corner café that opens early enough for dog walkers and commuters. The front bakery case is stacked with muffins and pastries, while the back café has a few tables for lingering. It’s pricier than some diners, but quality ingredients and consistent service justify it.

  • Price: $–$$ (~$9–$18)
  • MBTA/Parking: Back Bay (Orange Line) + short walk
  • Accessibility: Wheelchair accessible entrance; indoor seating
  • Link: southendbuttery.com

Back Bay

Back Bay Boston

The Friendly Toast — Back Bay

Bright, quirky décor and a menu that stretches from pancakes to breakfast burritos. They open at 7 a.m. and fill quickly on weekends, but weekdays are calmer. Portions are oversized, so splitting plates is common. Vegan scrambles, gluten-free pancakes, and almond milk lattes round out a menu that works for mixed groups.

  • Price: $–$$ (~$12–$18)
  • MBTA/Parking: Copley (Green Line)
  • Accessibility: Wheelchair accessible, large dining room
  • Link: thefriendlytoast.com

Flour Bakery + Café — Back Bay

Flour is Joanne Chang’s famous bakery-café, opening by 7 a.m. and staying steady until mid-afternoon. Sticky buns are the star, but breakfast sandwiches, yogurt parfaits, and good coffee keep it balanced. The atmosphere is friendly but bustling, so best for quick bites or takeaway. Gluten-free pastries rotate often, and staff mark allergens clearly.

  • Price: $–$$ (~$6–$15)
  • MBTA/Parking: Back Bay Station (Orange Line)
  • Accessibility: Wheelchair accessible, counter service
  • Link: flourbakery.com

Dorchester

Dorchester Boston

McKenna’s Café — Savin Hill, Dorchester

A true neighborhood diner that’s been running since the ’90s. Opens at 6 a.m. and is filled with locals grabbing eggs, pancakes, and bottomless coffee before work. Service is quick, and the staff know many by name. Prices are among the lowest in the city, making it a steady option for families and commuters.

  • Price: $ (~$7–$12)
  • MBTA/Parking: Savin Hill (Red Line)
  • Accessibility: Step entry, counter and booth seating
  • Link: mckennascafe.com

East Boston

East Boston

Angela’s Café — East Boston

Mexican breakfast served from 7 a.m., with huevos rancheros and chilaquiles that outshine most of the city’s brunch plates. It’s small and casual, with fast service and friendly staff. Regulars know to ask for extra salsa verde. It’s also a rare early-morning option for those who want something other than standard diner fare.

  • Price: $–$$ (~$10–$16)
  • MBTA/Parking: Maverick (Blue Line)
  • Accessibility: Small entry step; tight seating
  • Link: angelascafeboston.com

Caffè dell’Amore — East Boston

A cozy café that feels more European than Boston, with espresso drinks and fresh pastries ready when doors open at 7 a.m. Locals linger with cappuccinos, but they’ll pack up croissants and muffins quickly if you’re rushing to the T. Prices are modest, and it’s a quieter option than downtown cafés.

  • Price: $ (~$5–$12)
  • MBTA/Parking: Airport (Blue Line)
  • Accessibility: Small but accessible entrance, indoor tables
  • Link: caffedellosport.net

Recommendations

For classic diner plates, Mike’s City Diner and McKenna’s are the call. For pastries and lighter bites, Flour or South End Buttery shine. If you want international flair early, Angela’s is unmatched. And for students near Fenway, Tatte opens early and stays consistent.

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Filed Under: Best Of, Eat & Drink, Food

August 27, 2025 by Boston Southie

Boston’s neighborhoods each bring a slightly different personality to pizza. Some spots lean traditional, others push toppings in new directions, and many balance both. This guide keeps it simple: where to go, what to order, and how to get there by MBTA. Updated August 2025.


At-a-Glance

  • Neighborhoods: North End, South End, South Boston, East Boston, Back Bay, Fenway, Allston/Brighton, Jamaica Plain, Dorchester
  • MBTA stops: Haymarket, Back Bay, Broadway, Maverick, Hynes, Kenmore, Harvard Ave, Stony Brook, Fields Corner
  • Price tiers: $, $$, $$$
  • Wait/Resy notes: North End waits peak Fri–Sat; South End takes Resy; others walk-in friendly
  • Dietary tags: Gluten-free at select spots; vegan-friendly in JP and Allston
  • Hours/late-night: Many open until 11; Allston/Brighton and Fenway run later

North End — Regina Pizzeria

Regina has anchored the North End since 1926, and its coal-fired pies remain a steady draw. Expect a chewy, charred crust, tangy sauce, and a lively room that still feels old Boston. Go early or late to skip the long lines, and plan on pitchers and pies as the easy move.
Price: $ (~$15 per pie)
MBTA/Parking: Haymarket (Green/Orange)
Accessibility: Narrow doorway, small restrooms
Link: reginapizzeria.com

South End — Picco

Picco balances crisp thin-crust pizzas with a small but thoughtful beer list and its own ice cream counter. The pies come out blistered and light, and the pepperoni with hot honey has a loyal following. Weekends fill up, so book ahead; midweek nights are relaxed and easy. Families often land here because dessert is built-in.
Price: $$ (~$20–25 pp)
MBTA/Parking: Back Bay (Orange/Commuter Rail)
Accessibility: Step-free entry, tight tables
Link: piccorestaurant.com

South Boston — Capo

On West Broadway, Capo turns out Neapolitan-style pizzas alongside a full Italian menu. The Margherita is simple and solid, while seasonal pies bring new flavors. It works well for groups with mixed cravings, since the pasta program is strong too. Reservations make sense on weekends; weekday bar seats are often open.
Price: $$ (~$22–28 pp)
MBTA/Parking: Broadway (Red Line)
Accessibility: Ramp entrance, accessible restrooms
Link: caposouthboston.com

East Boston — Santarpio’s

Santarpio’s is straightforward: cash only, paper plates, and thin-crust pies that define Eastie comfort food. The sausage and garlic pizza is the standard order, and the room is noisy in a good way. Expect a line at peak hours but quick turnover once you’re inside.
Price: $ (~$15–20 per pie)
MBTA/Parking: Maverick (Blue Line)
Accessibility: Narrow step at entrance, no dedicated restroom
Link: santarpiospizza.com

Back Bay — Eataly Pizza & Pasta

Inside Prudential Center, Eataly serves Roman-style pizza with crisp crusts and clean toppings. It’s reliable for a quick lunch, a pre-Fenway bite, or a group meal when not everyone wants pizza. Slices are quick, tables run busier, but turnover is steady.
Price: $$ (~$20–25 pp)
MBTA/Parking: Hynes (Green Line)
Accessibility: Full ADA access
Link: eataly.com

Fenway — Tasty Burger Pizza Nights

Tasty Burger isn’t a pizza shop first, but its late-night slices keep Fenway crowds happy after games. The pies are simple, the service is quick, and the vibe is casual. It’s a dependable option when you need food after 11 p.m. without much fuss.
Price: $ (~$5–6 per slice)
MBTA/Parking: Kenmore (Green Line)
Accessibility: Step-free entrance, casual seating
Link: tastyburger.com

Allston/Brighton — Otto Pizza

Otto brought Portland’s mix-and-match topping style to Harvard Ave, and its slices have become a neighborhood standard. The mashed potato, bacon, and scallion pie is surprisingly balanced, and vegan-friendly options broaden the appeal. Hours stretch later than most, making it a strong late-night stop.
Price: $ (~$5–6 per slice; $20–25 per pie)
MBTA/Parking: Harvard Ave (Green Line B)
Accessibility: Narrow but step-free entry
Link: ottoportland.com

Jamaica Plain — Same Old Place

Same Old Place keeps Greek-style pan pizza alive in JP with thick, cheesy pies that have been on order sheets for decades. It’s neighborhood food at its core, reliable for delivery and casual dine-in alike. Calzones and subs round out the comfort-heavy menu.
Price: $ (~$15–20 per pie)
MBTA/Parking: Stony Brook (Orange Line)
Accessibility: Street-level entry, limited seating
Link: sameoldplacepizza.com

Dorchester — Molinari’s Pizzeria

Dorchester Center’s Molinari’s keeps things simple in the best way: thin crust, wood-fired pies made from fresh ingredients in a cozy open-kitchen setting. It’s a sit-down spot with a warm neighborhood feel and dependable flavor—a good replacement for the defunct Venice Pizza.
Price: Moderate
MBTA/Parking: Near Adams St/Lower Mills (Red Line); street parking available
Accessibility: Casual interior; check for accessibility details
Link: molinarispizzeria.com

Night shot of a boston skyline from the water

Filed Under: Best Of, Eat & Drink, Food

August 27, 2025 by Boston Southie

Cannoli aren’t just dessert in Boston, they’re tradition. From legendary North End bakeries to modern spins in Somerville, Cambridge, and beyond, the city’s cannoli scene is unmatched. This guide highlights the must-try spots where crispy shells and creamy ricotta fillings shine.

Stack of Cannolis from a south Boston store

At-a-Glance

  • Neighborhoods: North End, Somerville, Cambridge, South End, Quincy
  • MBTA stops: Haymarket, Davis, Harvard, Back Bay, Quincy Center
  • Price tiers: $–$$ ($4–$7 per cannoli)
  • Wait/Resy notes: Weekend lines in North End; shorter waits elsewhere
  • Hours: Most open daily; Bova’s is 24/7

North End

Mike’s Pastry — North End
Mike’s is the heavyweight of Boston cannoli, and the shop’s blue-and-white boxes are practically souvenirs. Expect oversized pastries stuffed with everything from classic ricotta to pistachio, espresso, and amaretto. The shells stay crunchy even under heaps of filling, making them ideal for sharing, though few people actually do. Weekend lines wrap down Hanover Street, but the energy, history, and payoff make the wait worthwhile.

  • Price: $–$$ (~$5–$7 per cannoli)
  • MBTA/Parking: Haymarket (Orange/Green Line)
  • Accessibility: Narrow, crowded interior
  • Link: mikespastry.com

Modern Pastry — North End
Family-owned and often the locals’ pick, Modern Pastry is all about choice. Customers can select plain or chocolate-dipped shells, pick their filling, and decide on toppings like chocolate chips or powdered sugar. The cannoli are slightly smaller than Mike’s, but their crispness and smooth ricotta filling give them staying power. With additional cakes, cookies, and tarts on display, it’s a bakery that rewards repeat visits.

  • Price: $ (~$4–$6 per cannoli)
  • MBTA/Parking: Haymarket (Orange/Green Line)
  • Accessibility: Step at entry
  • Link: modernpastry.com

Bova’s Bakery — North End
Bova’s is the North End’s answer to every late-night craving, serving cannoli 24/7. The shells are fried golden and filled with traditional ricotta, less sweet than some competitors, which makes them appealing for purists. Crowds are smaller here, so you can avoid the Hanover Street rush while still enjoying top-tier cannoli. Beyond pastries, the bakery also offers bread, cookies, and hearty sandwiches, but cannoli remain a highlight.

  • Price: $ (~$4–$6 per cannoli)
  • MBTA/Parking: Haymarket (Orange/Green Line)
  • Accessibility: Narrow entry, busy counter
  • Link: bovabakeryboston.net

Somerville

Lyndell’s Bakery — Union Square
Founded in 1887, Lyndell’s is one of the oldest bakeries in the Boston area, and its cannoli remain a neighborhood classic. The shells are crisp, the ricotta lightly sweetened, and the vibe pure old-school charm. Though Lyndell’s is better known for sheet cakes and cookies, regulars will tell you their cannoli are underrated gems. The pace is slower than Hanover Street, and you’ll usually find friendly service and no wait.

  • Price: $ (~$4–$5 per cannoli)
  • MBTA/Parking: Union Square (Green Line)
  • Accessibility: Step at entrance
  • Link: lyndells.com

La Saison Bakery — Somerville
A relative newcomer, La Saison blends creativity with respect for tradition. Cannoli are filled to order, ensuring shells stay crisp, and often come accented with toppings like candied orange peel or a drizzle of chocolate. The ricotta filling is smooth and balanced, never overly sweet. For those looking for a modern spin that still honors the original, this is one of Somerville’s best bets.

  • Price: $ (~$5–$6 per cannoli)
  • MBTA/Parking: Davis (Red Line)
  • Accessibility: Wheelchair accessible
  • Link: lasaison-bakery.com


Cambridge

Royal Pastry Shop — Harvard Square
Royal Pastry Shop feels frozen in time, in the best way possible. The bakery’s cannoli are straightforward: crisp shells, smooth ricotta, and no frills. It’s not flashy, but it’s the kind of dessert you keep going back for, with flavors that have been consistent for decades. Harvard students and longtime locals alike treat it as a dependable go-to.

  • Price: $ (~$4–$5 per cannoli)
  • MBTA/Parking: Harvard (Red Line)
  • Accessibility: Narrow doorway
  • Link: royalpastryshop.net

Flour Bakery + Café — Cambridge
Best known for its sticky buns and breakfast sandwiches, Flour also makes cannoli worth seeking out. The filling is creamier and slightly sweeter than old-school versions, making it more of a dessert-style treat. Freshly made shells keep their snap, and the café setting makes it easy to pair one with coffee or a sandwich. It’s an option that bridges the line between traditional and modern tastes.

  • Price: $–$$ (~$5–$7 per cannoli)
  • MBTA/Parking: Central (Red Line)
  • Accessibility: Wheelchair accessible
  • Link: flourbakery.com

South End

Roma Bakery — South End
Roma Bakery channels Hanover Street without the lines, offering breads, cookies, and cannoli that hold their own against North End heavyweights. The shells are sturdy and travel-friendly, while the ricotta is lightly sweetened with subtle vanilla notes. It’s a great choice for picking up desserts before dinner parties, as everything here stays fresh well into the evening. Compared to the bustle of Hanover Street, Roma feels like a hidden neighborhood treasure.

  • Price: $ (~$4–$6 per cannoli)
  • MBTA/Parking: Back Bay (Orange Line)
  • Accessibility: Wheelchair accessible
  • Link: romabakeryboston.com

Mida — South End
While known primarily as an Italian restaurant, Mida’s dessert menu includes standout cannoli. They’re filled to order, ensuring the shells remain crisp, and the ricotta is smooth, balanced, and lightly sweet. A drizzle of chocolate and delicate presentation elevate them from casual pastry to plated dessert. It’s a refined way to finish a meal of house-made pasta or braised meats.

  • Price: $$ (~$7 per cannoli)
  • MBTA/Parking: Back Bay (Orange Line)
  • Accessibility: Wheelchair accessible
  • Link: midarestaurant.com

Quincy

Konditor Meister — Quincy
Konditor Meister is renowned for its elaborate cakes, but its cannoli are equally polished. The shells are perfectly crisp, the ricotta filling is rich but not overly sweet, and every pastry looks presentation-ready. This is the bakery people turn to for catering, weddings, and special occasions, where desserts need to taste as good as they look. Slightly pricier than most, but the attention to detail makes it well worth it.

Picture of Cannolis at a South Boston Bar
  • Price: $$ (~$6–$7 per cannoli)
  • MBTA/Parking: Quincy Adams (Red Line)
  • Accessibility: Large, wheelchair accessible bakery
  • Link: konditormeister.com

Filed Under: Best Of, Eat & Drink, Food

August 27, 2025 by Boston Southie

From champagne to shakshuka, Boston’s brunch scene covers everything from boozy weekends to family-friendly mornings. Here’s where to brunch by neighborhood.


At-a-Glance

  • Neighborhoods: South End, Cambridge, North End, Jamaica Plain, Seaport
  • MBTA stops: Back Bay, Kendall, Haymarket, Stony Brook, Courthouse
  • Price tiers: $–$$$ (most brunch plates $12–$28)
  • Wait/Resy notes: Reservations recommended in South End and Seaport
  • Dietary tags: Vegetarian, vegan, gluten-free options available
  • Hours: Most open 9 a.m.–3 p.m. weekends
Boston Brunch spread

South End

The Beehive — South End
Known for live jazz and a vibrant weekend crowd, The Beehive pairs classic brunch dishes with cocktails and a buzzy atmosphere. The shakshuka and smoked salmon plates hold their own, while the bottomless coffee keeps things grounded. It’s a bit chaotic at peak times, but the scene is part of the draw. Reservations are smart here, especially after 11 a.m.

  • Price: $$–$$$ (~$18–$28 plates)
  • MBTA/Parking: Back Bay (Orange Line)
  • Accessibility: Wheelchair accessible, large dining room
  • Link: beehiveboston.com

Boston Chops — South End
A steakhouse that transforms brunch into a hearty feast. Expect oversized portions like steak and eggs, fried chicken sandwiches, and rich Benedicts. The dining room is upscale but relaxed in the morning, with good service and strong coffee. A better fit for groups who want a filling brunch over a light bite.

  • Price: $$–$$$ (~$20–$28 plates)
  • MBTA/Parking: Back Bay (Orange Line)
  • Accessibility: Wheelchair accessible, reservations recommended
  • Link: bostonchops.com

Cambridge

Cafe Luna — Kendall Square
Cafe Luna has long been a brunch staple, with a menu that balances sweet and savory. Nutella-stuffed French toast and crab cake Benedicts headline, while vegan scrambles and smoothies cover other bases. The space is bright and busy, and lines form quickly, so reservations are key on weekends. Service is efficient even when it’s packed.

  • Price: $$ (~$15–$25 plates)
  • MBTA/Parking: Kendall/MIT (Red Line)
  • Accessibility: Wheelchair accessible, indoor/outdoor seating
  • Link: cafeluna-centralsq.com

Henrietta’s Table — Harvard Square
Farm-to-table brunch that leans seasonal, with produce sourced locally. Think maple sausage, farm eggs, and rotating baked goods. The space feels warm and classic, drawing both Harvard families and longtime Cambridge locals. It’s not flashy, but quality is consistently high.

  • Price: $$–$$$ (~$20–$28 plates)
  • MBTA/Parking: Harvard (Red Line)
  • Accessibility: Wheelchair accessible, spacious dining room
  • Link: charleshotel.com/dining/henriettas-table

North End

Brunch spread from a South Boston restaurant

Parla — North End
Parla is better known for cocktails, but its weekend brunch pulls a loyal crowd. Plates like lemon ricotta pancakes and breakfast pastas mix with strong coffee and morning drinks. The atmosphere is moody but welcoming, and it feels like a hidden escape from the busier Hanover Street brunch lines.

  • Price: $$ (~$16–$24 plates)
  • MBTA/Parking: Haymarket (Green/Orange Line)
  • Accessibility: Small entry step, dim dining room
  • Link: parlaboston.com

Bricco — North End
An upscale Italian restaurant that runs a polished weekend brunch. Eggs, pastries, and paninis anchor the menu, with a European feel. Seating is tighter than some brunch spots, but service is attentive and quick. Best for smaller groups or pairs who want a more refined brunch.

  • Price: $$–$$$ (~$18–$26 plates)
  • MBTA/Parking: Haymarket (Green/Orange Line)
  • Accessibility: Narrow doorway, limited tables
  • Link: bricco.com

Jamaica Plain

The Haven — JP
Boston’s Scottish gastropub opens for brunch with hearty plates like Scotch eggs, smoked salmon toast, and full breakfasts. It’s casual but with a twist, and their beer list means brunch can stretch into the afternoon. Families mix with regulars, and the service is unfussy. Portions are generous for the price.

  • Price: $$ (~$14–$20 plates)
  • MBTA/Parking: Stony Brook (Orange Line)
  • Accessibility: Wheelchair accessible, cozy dining room
  • Link: thehavenjp.com

Brassica Kitchen — JP
Creative and seasonal, Brassica Kitchen blends comfort and innovation on its brunch menu. Expect fried chicken and waffles, kimchi scrambles, and inventive pastries. The vibe is laid-back but stylish, making it a destination for food-focused brunchers. It’s a spot where you’ll want to linger with a coffee refill.

  • Price: $$–$$$ (~$16–$24 plates)
  • MBTA/Parking: Forest Hills (Orange Line)
  • Accessibility: Wheelchair accessible, neighborhood spot
  • Link: brassicakitchen.com

Seaport

Committee — Seaport
Mediterranean-inspired brunch with strong cocktails and small plates for sharing. The Greek yogurt bowls and spanakopita Benedicts stand out, and the energy is lively even at 10 a.m. The large space fills quickly, so reservations are strongly advised. Expect a social scene more than a quiet meal.

South Boston Brunch spread
  • Price: $$–$$$ (~$18–$26 plates)
  • MBTA/Parking: Courthouse (Silver Line)
  • Accessibility: Wheelchair accessible, high-energy dining room
  • Link: committeeboston.com

Filed Under: Best Of, Eat & Drink, Food

August 27, 2025 by Boston Southie

Boston’s green spaces make it easy to get kids outside without committing to a full-day hike. These five trails balance stroller-friendly paths, bathrooms, and MBTA access, with enough variety to keep everyone from toddlers to teens engaged. Updated August 2025.


At-a-Glance

  • Neighborhoods: JP, Dorchester, East Boston, Milton, Medford
  • MBTA stops: Forest Hills, JFK/UMass, Maverick, Mattapan Trolley, Oak Grove
  • Surfaces: Mix of paved, gravel, and dirt
  • Bathrooms: Available at major trailheads
  • Dogs: Allowed on leash in most areas
  • Quiet times: Early mornings, weekdays
  • Updated: August 2025
Trail Sign on a hiking trail in South Boston

Arnold Arboretum — Jamaica Plain

The Arboretum’s paved main loop is stroller- and wheelchair-friendly, making it one of the most reliable spots for families year-round. Side trails let older kids climb hills and explore, while toddlers can stay on flat paths near the Hunnewell Visitor Center. Bathrooms are open seasonally, and the MBTA Forest Hills stop is a ten-minute walk away. Mornings before 10am are the calmest for families who prefer a quieter experience.
Trail length: Up to 3 miles
Surface: Paved with optional dirt side trails
Bathrooms: At Visitor Center (seasonal)
Dogs: Allowed on leash
MBTA/Parking: Forest Hills (Orange Line); limited parking
Link: arboretum.harvard.edu

Blue Hills Reservation — Milton

Just outside the city, Blue Hills offers family-friendly options without the intensity of its longer trails. The Eliot Tower loop provides a short, rewarding climb, while Houghton’s Pond has a flat, stroller-accessible path with picnic areas. Bathrooms and snack stands are near the pond in season, and parking lots make it an easy weekend drive. Expect crowds on peak fall weekends.
Trail length: 1–3 miles
Surface: Mix of gravel, dirt, paved near pond
Bathrooms: At Houghton’s Pond
Dogs: Allowed on leash
MBTA/Parking: Mattapan Trolley + bus; ample parking
Link: mass.gov/locations/blue-hills-reservation

Trail view of a hiking trail near boston

Middlesex Fells — Medford

The Fells’ Spot Pond area is a family favorite, with wide, well-marked trails and plenty of space to explore. The Reservoir Trail loop is manageable for older kids and teens, while younger ones can enjoy short strolls by the water. Bathrooms are at the Botume House Visitor Center. On weekends, bring snacks—there aren’t food vendors on site. Accessible by MBTA with a short walk, or by car with several parking lots nearby.
Trail length: 1–2.5 miles
Surface: Dirt and gravel
Bathrooms: At Visitor Center
Dogs: Allowed on leash
MBTA/Parking: Oak Grove (Orange Line) + 15-min walk; parking lots available
Link: friendsofthefells.org

Neponset River Greenway — Dorchester/Mattapan

This paved riverside trail is perfect for strollers, scooters, and bikes. Families can start near Pope John Paul II Park and follow the flat path along the Neponset River. The trail is dotted with playgrounds and benches, making it easy to break up the outing for little ones. Bathrooms are near the park entrances. The Mattapan Trolley connects directly to the trail, making it one of the most MBTA-friendly greenways.
Trail length: Up to 5 miles (out and back)
Surface: Fully paved
Bathrooms: At Pope John Paul II Park
Dogs: Allowed on leash
MBTA/Parking: Mattapan Trolley; free parking lots
Link: mass.gov/locations/neponset-river-reservation

Belle Isle Marsh — East Boston

Shot of a Boston Bay Island near a hiking trail

Boston’s only salt marsh offers short, flat boardwalk trails where kids can spot herons, egrets, and other wildlife. It’s an easy introduction to nature walks without leaving the city. Bathrooms are available seasonally, and benches along the loop let families rest. The Maverick stop on the Blue Line is a quick ride from downtown, and the marsh feels surprisingly peaceful given its proximity to Logan Airport.
Trail length: 0.5–1 mile
Surface: Boardwalk and gravel
Bathrooms: Seasonal facilities
Dogs: Allowed on leash
MBTA/Parking: Maverick (Blue Line); small parking lot
Link: mass.gov/locations/belle-isle-marsh-reservation

Filed Under: Best Of, Family, Nature, Outdoors

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