Family

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.

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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

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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)

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)

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

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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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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.

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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

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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

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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

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