Boston Southie

Things To Do In The City

Things To Do In The City

Outdoors

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Boston’s bike scene shines in every season, but fall brings extra color to the region’s rail trails and riverside paths. These eight routes balance convenience, scenery, and rideability, with MBTA access and suburban reach for anyone planning a two‑wheeled outing.

At-a-Glance

  • Start points: Boston, Cambridge, Somerville, Newton, Concord
  • Time: 1–4 hours
  • Distance: 3–20 miles
  • Surfaces: Paved or stone dust
  • Bathrooms/water: Available at most trailheads and parks
  • MBTA/parking: Red, Orange, Green lines; commuter rail options
  • Dogs/strollers: Allowed on multi-use paths
  • Season: Year-round, best foliage Sept–Nov
White Bike on a Boston Trail

Charles River Bike Path

The Charles River Bike Path is Boston’s signature ride, stretching about 17 miles from the Museum of Science to Norumbega Park in Newton. It offers flat, paved miles alongside the water, with skyline views and leafy stretches perfect for fall foliage. Popular with commuters and casual riders alike, it connects seamlessly with city parks. Expect some crowding on weekends, but the views are worth it.

  • Distance: ~17 miles
  • Surfaces/elevation: Paved, flat with some road crossings
  • Bathrooms/water: Public restrooms at Esplanade, BU Bridge, Herter Park
  • MBTA/parking: Red and Green lines at multiple entry points
  • Dogs/strollers: Multi-use friendly
  • Season/cautions: Year-round; fall brings heavy leaf‑peeping traffic
  • Link: mass.gov/charles-river-bike-path
  • Last checked: Aug 25, 2025

Southwest Corridor Park

Running four miles from Back Bay to Forest Hills, the Southwest Corridor Park is a green commuter artery through the South End and Jamaica Plain. The paved path passes playgrounds, basketball courts, and gardens, making it lively but not overwhelming. It’s a reliable ride for anyone seeking color without leaving the city. Evenings bring heavier bike traffic, but mornings are calm.

  • Distance: 4–5 miles
  • Surfaces/elevation: Paved, flat
  • Bathrooms/water: Available at Ruggles and Forest Hills
  • MBTA/parking: Orange Line along route
  • Dogs/strollers: Multi-use, family friendly
  • Season/cautions: Best in fall for tree color; watch for commuter cyclists
  • Link: boston.gov/southwest-corridor-park
  • Last checked: Aug 25, 2025

Minuteman Bikeway

Tracing Paul Revere’s historic ride, the Minuteman Bikeway runs from Alewife Station through Arlington and Lexington to Bedford. Over 10 miles of paved rail trail, it’s shaded and wide, with plenty of trailheads and signage. In fall, the leafy canopy adds a vibrant backdrop. Popular with both leisure riders and distance cyclists, it’s one of the region’s most beloved paths.

  • Distance: 10.1 miles
  • Surfaces/elevation: Paved, gentle grades
  • Bathrooms/water: Arlington Center and Lexington Depot
  • MBTA/parking: Red Line Alewife; parking in Arlington and Bedford
  • Dogs/strollers: Allowed
  • Season/cautions: Year-round; peak fall weekends are busy
  • Link: minutemanbikeway.org
  • Last checked: Aug 25, 2025

Arnold Arboretum Loop

Within Boston’s Arnold Arboretum, this 4.5-mile loop mixes gentle climbs with vibrant fall foliage. Paved roads wind past historic plantings and sweeping views of Boston from Peters Hill. Cyclists share space with walkers, but wide roads and slow traffic keep it relaxed. It’s best enjoyed as a leisurely ride paired with leaf peeping.

  • Distance: 4.5 miles
  • Surfaces/elevation: Paved, rolling hills
  • Bathrooms/water: Visitor Center at Arborway entrance
  • MBTA/parking: Orange Line Forest Hills; street parking nearby
  • Dogs/strollers: Dogs on leash; stroller-friendly
  • Season/cautions: Gorgeous in fall; some paths close in icy weather
  • Link: arboretum.harvard.edu
  • Last checked: Aug 25, 2025

Deer Island Trail

Deer Island offers a 4.6-mile paved perimeter loop with harbor views and historic markers. The ride mixes breezy shoreline with rolling terrain, plus access to picnic areas and restrooms. It’s a tranquil alternative to city rides, especially in fall when the air is crisp and crowds are thinner. A ferry ride adds adventure for those starting downtown.

  • Distance: 4.6 miles
  • Surfaces/elevation: Paved, rolling
  • Bathrooms/water: Facilities near trailhead
  • MBTA/parking: Ferry from Long Wharf; parking on site
  • Dogs/strollers: Allowed
  • Season/cautions: Best fall views; windy in winter
  • Link: mwra.com/deer-island
  • Last checked: Aug 25, 2025

Somerville Community Path

The Somerville Community Path extends 3.2 miles through Davis Square and toward East Cambridge. Recently expanded, it links smoothly with the Green Line Extension and Red Line at Alewife. The path is paved and lined with murals, trees, and neighborhood energy. In fall, the blend of foliage and city makes it one of the best short rides.

A shot of Boston Skyscrapers from a bike lane
  • Distance: 3.2 miles
  • Surfaces/elevation: Paved, flat
  • Bathrooms/water: Limited along route; Davis Square nearby
  • MBTA/parking: Red Line Alewife, Green Line Lechmere
  • Dogs/strollers: Allowed
  • Season/cautions: Year-round; short but highly used
  • Link: somervillema.gov/communitypath
  • Last checked: Aug 25, 2025

Bruce Freeman Rail Trail

Stretching over 20 miles from Lowell through Acton and Concord, the Bruce Freeman Rail Trail is one of the longest suburban rides near Boston. Wide and well-maintained, it passes wetlands, woodlands, and neighborhoods, all lit up in fall color. Cyclists love it for long-distance, low‑stress riding. Future expansions will add even more mileage.

  • Distance: 20 miles (current open section)
  • Surfaces/elevation: Paved, flat to rolling
  • Bathrooms/water: Town centers along route
  • MBTA/parking: Commuter rail Concord/Acton; trailhead parking
  • Dogs/strollers: Allowed
  • Season/cautions: Stunning foliage in fall; open year-round
  • Link: brucefreemanrailtrail.org
  • Last checked: Aug 25, 2025

Mass Central Rail Trail (Wayside)

The Mass Central Rail Trail’s Wayside section links Weston, Wayland, and Waltham. Still expanding, it features a mix of paved and stone‑dust surfaces through woods and wetlands. It’s less busy than Minuteman, offering a quieter suburban alternative. Fall highlights include colorful foliage and peaceful wetland views.

Bikers at night in Boston
  • Distance: 10+ miles (varies by open sections)
  • Surfaces/elevation: Paved and stone dust
  • Bathrooms/water: Trailheads in Weston and Wayland
  • MBTA/parking: Commuter rail to Waltham; parking at trailheads
  • Dogs/strollers: Allowed
  • Season/cautions: Best in fall for foliage; incomplete connections
  • Link: masscentralrailtrail.org
  • Last checked: Aug 25, 2025

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Boston’s outdoors don’t shut down when the air turns crisp. From harbor views to wooded trails, these escapes are all inside city limits, MBTA-accessible, and perfect for fall foliage strolls or winter refreshers.

Route Overview

These 9 outdoor escapes offer a mix of waterfront loops, urban parks, and wooded trails. Each is within Boston proper, reachable by MBTA, and suitable for year-round visits, with notes on surfaces, bathrooms, dogs, and stroller access. The list balances iconic spots with quieter retreats.

A shot from over the water taken in Boston's Back Bay area

Waypoints

Harborwalk Loop — Seaport to North End

A flat, easy route along Boston Harbor that shines in fall with crisp skyline views. In winter, bundle up; the wind can cut sharp but crowds are light. Start in Seaport, pass Fan Pier, and trace the water toward the North End for hot chocolate after. The variety of views, from the Seaport skyline to old wharves, make this an urban walk that feels fresh every season.

  • Distance/Surface: ~3 miles; paved/boardwalk, flat
  • Bathrooms/Water: Seaport Common restrooms, Faneuil Hall
  • MBTA/Parking: Silver Line Courthouse; Aquarium stop
  • Dogs/Strollers: Both welcome; stroller-friendly
  • Season: Year-round; best in fall afternoons

Arnold Arboretum — Jamaica Plain

Harvard’s living museum of trees is spectacular in October with maples glowing red. In winter, its quiet hills and open meadows make for brisk walks. Peters Hill offers skyline views worth the climb. The Arboretum’s variety of species means the scenery changes week to week, rewarding repeat visits.

  • Distance/Surface: Variable; paved paths, dirt trails, moderate elevation
  • Bathrooms/Water: Visitor Center restrooms
  • MBTA/Parking: Orange Line Forest Hills; free street parking nearby
  • Dogs/Strollers: Dogs on leash; stroller-friendly main paths
  • Season: Year-round; peak fall foliage mid-October

Jamaica Pond — Jamaica Plain

This 1.5-mile loop is a city favorite for reflective water views. In fall, leaves frame the pond; in winter, it’s peaceful and often icy. Easy walking, popular with joggers and families. Seasonal sailing programs and summer concerts give it year-round appeal, but fall foliage around the water is unmatched.

  • Distance/Surface: 1.5-mile loop; paved, flat
  • Bathrooms/Water: Seasonal restrooms near Boathouse (VERIFY HOURS)
  • MBTA/Parking: Green E Heath or Orange Line Stony Brook + walk
  • Dogs/Strollers: Dogs on leash; stroller accessible
  • Season: Year-round; quieter in winter

Charles River Esplanade — Back Bay

One of Boston’s classic urban escapes. In fall, tree-lined paths along the river burst with color. In winter, bundled joggers and skaters on the Hatch Shell ice rink keep it lively. Bridges connect multiple entry points. The Esplanade is also a hub for seasonal events, from fitness classes to concerts, making it a cultural as well as scenic landmark.

  • Distance/Surface: 3+ miles; paved, flat with bridges
  • Bathrooms/Water: Seasonal restrooms (VERIFY HOURS)
  • MBTA/Parking: Green Line Arlington; limited parking
  • Dogs/Strollers: Dogs allowed; stroller-friendly
  • Season: Year-round; fall foliage and winter skating highlight

Franklin Park — Dorchester/Roxbury

Boston’s largest park offers woodsy trails, open meadows, and fall color that feels far from city streets. Winter adds quiet and space for snowshoeing. Historic stone ruins and the zoo add variety. The range of terrain here, from shaded woods to open fields, makes it one of the city’s most versatile escapes.

  • Distance/Surface: Multiple loops; dirt and paved; rolling hills
  • Bathrooms/Water: Zoo restrooms; seasonal park facilities
  • MBTA/Parking: Orange Line Green St; free parking lots
  • Dogs/Strollers: Dogs welcome; stroller-friendly on main paths
  • Season: Year-round; especially scenic in fall

East Boston Greenway & Piers Park — East Boston

Trail shot from a Boston Trail

This stretch links neighborhood parks to harbor views with skyline backdrops. Fall sunsets glow over downtown. In winter, brisk walks with fewer crowds make it a hidden gem. The combination of playgrounds, gardens, and waterfront overlooks makes it as good for families as it is for solo walks.

  • Distance/Surface: ~2 miles; paved, flat
  • Bathrooms/Water: Piers Park boathouse restrooms (VERIFY HOURS)
  • MBTA/Parking: Blue Line Maverick; limited street parking
  • Dogs/Strollers: Both welcome; stroller-friendly
  • Season: Year-round; fall sunsets especially stunning

Castle Island & Pleasure Bay — South Boston

A coastal walk with history and ocean breezes. In fall, it’s crisp and bright; in winter, it’s bracing but rewarding. Fort Independence anchors the loop, with planes overhead adding urban drama. Sullivan’s snack stand (seasonal) makes it a popular summer spot too, but the quieter months reveal its serene side.

  • Distance/Surface: 2+ miles; paved, flat
  • Bathrooms/Water: Sullivan’s restrooms (VERIFY HOURS)
  • MBTA/Parking: Red Line Broadway + bus; free parking lots
  • Dogs/Strollers: Dogs on leash; stroller-friendly
  • Season: Year-round; less crowded in colder months

Charlestown Navy Yard — Charlestown

History meets harbor views here. The walk along dry docks and piers offers crisp fall air and dramatic winter harbor light. USS Constitution nearby makes it a cultural stop as well. The wide piers and calm paths make this one of the easiest harbor walks for families with strollers or older adults.

  • Distance/Surface: ~1 mile; paved, flat
  • Bathrooms/Water: Navy Yard visitor restrooms
  • MBTA/Parking: Orange Line Community College; ferry in season
  • Dogs/Strollers: Dogs welcome; stroller-friendly
  • Season: Year-round; winter light and harbor views highlight

Boston Common & Public Garden — Downtown/Back Bay

Bike Rack in Boston

Boston’s central green spaces shine in fall with leaf-lined paths. Winter adds ice skating at Frog Pond, making it lively even in the cold. Easy access and iconic views make it a go-to escape. The blend of history, monuments, and seasonal activities means there’s always something to see or do here.

  • Distance/Surface: Variable; paved paths, flat
  • Bathrooms/Water: Frog Pond restrooms (VERIFY_HOURS)
  • MBTA/Parking: Green/Red Line Park St; underground garage
  • Dogs/Strollers: Dogs on leash; stroller-friendly
  • Season: Year-round; skating in winter, foliage in fall

Safety & Access

All routes are MBTA-accessible with paved or mostly flat surfaces. Bathrooms are seasonal at some parks (noted with VERIFY HOURS). Dogs are generally welcome on leash. Winter walkers should dress in layers and be mindful of icy spots.

When to Go

  • Fall: Peak foliage mid-October at Arboretum, Franklin Park, and Esplanade. Crisp harbor walks shine in November.
  • Winter: Castle Island and Charlestown Navy Yard for bracing harbor air; Boston Common for skating. Quieter loops at Jamaica Pond and Franklin Park.

Year-round staples: Harborwalk, Esplanade, and Arboretum.

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The Head of the Charles Regatta brings two days of nonstop rowing to the river each October, and Boston’s banks fill with spectators. If you want to stay on the Boston side (without crossing into Cambridge), here are six of the best spots to take in the action, along with tips on food, access, and the best times to visit.

At-a-Glance

  • Neighborhoods: Back Bay, Allston/Brighton, Fenway, Beacon Hill
  • MBTA stops: Kenmore, Hynes, Harvard Ave, Charles/MGH
  • Best timing: Saturday morning for practice runs, Sunday afternoon for finals
  • Crowds: Heavy both days; arrive early for bridges
  • Food nearby: Beer gardens, cafes, and food trucks

Updated: August 2025

Weeks Footbridge — Back Bay

Weeks Footbridge is the iconic crossing point with panoramic views up and down the Charles. It’s one of the busiest spectator spots, so plan to arrive early if you want rail space. The flat bridge deck makes it easy to linger, and Harvard Square food trucks often line up nearby, so you can grab coffee or a sandwich before heading over. Bathrooms are limited, so plan ahead.
Cost: Free
MBTA/Parking: Harvard (Red Line), 10–12 min walk
Accessibility: Fully pedestrian bridge, level surface
Link: hocr.org

BU Bridge — Allston/Brighton

Shot of the Boston bay during Head of the Charles Race

The BU Bridge gives a sweeping perspective of crews as they come around the bend toward Cambridge. Crowds are lighter than at Weeks or Anderson, and you can walk down to Magazine Beach on the Boston side if you want more open space. After the races, grab pizza or beer in Allston, just a ten-minute walk away.
Cost: Free
MBTA/Parking: Boston University Central (Green Line B)
Accessibility: Narrow sidewalks; steep approach
Link: hocr.org

Anderson Memorial Bridge — Allston/Brighton

Anderson Bridge connects directly into Harvard Square but gives a solid Boston-side view of passing boats. It’s packed by midday, so the trick is to show up early or linger later in the afternoon when turnover happens. Food trucks cluster on both ends, and there’s usually a festive atmosphere. Restrooms are a walk away in Harvard Square.
Cost: Free
MBTA/Parking: Harvard Ave (Green Line B) + 15-min walk
Accessibility: Narrow sidewalks; crowd-heavy
Link: hocr.org

Charles River Esplanade — Back Bay/Fenway

The Esplanade runs for miles along the river, and it’s one of the most flexible viewing options. Families spread blankets on the grass near the BU Boathouse, while runners and cyclists weave through the crowd. Bring snacks or stop at a Back Bay café beforehand, since food options along the river itself are limited. Bathrooms are available at a couple of Esplanade facilities and are open from 8 AM to 6 PM, but lines may form.
Cost: Free
MBTA/Parking: Hynes (Green Line), 8–10 min walk
Accessibility: Paved paths; stroller- and wheelchair-friendly
Link: esplanade.org

Eliot Bridge — Allston/Brighton

Image of a Canoe during a race in the Boston Bay

At the bend near the finish stretch, Eliot Bridge offers a high vantage point and a little more breathing room than the central bridges. It’s still busy, but you’ll often find local families and alumni groups setting up tents nearby. Grab coffee in Allston or Fenway on your way, since food is less plentiful here. Bathrooms are scarce, so plan to walk back toward Harvard Square or the Esplanade.
Cost: Free
MBTA/Parking: Harvard Ave (Green Line B) or Central (Red Line) + 15-min walk
Accessibility: Narrow sidewalks, uneven pavement
Link: hocr.org

Charles/MGH Riverfront — Beacon Hill

Near the Charles/MGH station, you’ll find wide sidewalks and benches along the river, offering a calmer perspective than the busy bridges upriver. It’s an easy meet-up point for friends, and you can pair it with brunch on Charles Street afterward. Restrooms are inside the Red Line station.
Cost: Free
MBTA/Parking: Charles/MGH (Red Line)
Accessibility: Paved paths, ADA access
Link: hocr.org