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Trails near South Boston, MA

1,076 trails within 30 miles of South Boston, for hiking, biking, horseback riding and off-road riding. Tap a trail for its map, trailhead and directions.

Hiking trails (1,014) Walking trails (987) Bike trails (381) Mountain bike trails (294) Paved trails (158) Horse trails (68) ATV and UTV trails (3) Dirt bike trails (8) Off-road and 4x4 trails (4) Dog-friendly trails (27) Snowmobile trails (11) Cross-country ski trails (13) Wheelchair-accessible trails (16) Rail trails (22) Greenways (16)

Quick picks

All nearby trails

South Bay Harbor Trail

1.0 mi away

0.5 mi long · Easy · Dogs on leash · South Boston

Hiking Biking Paved Wheelchair accessible Dogs allowed

South Bay Harbor Trail

1.2 mi away

2.5 mi long · Easy · Dogs on leash · South Boston

Hiking Biking Paved Wheelchair accessible Dogs allowed

Lagoon Path

1.8 mi away

0.5 mi long · Easy · Dogs on leash · Friends of the Public Garden

Hiking Paved Wheelchair accessible Dogs allowed

Washington-Rochambeau Revolutionary Route National Historic Trail

1.8 mi away

0.3 mi long · Easy · Boston

Hiking Paved

Boston Boundless Trail Section 1

1.9 mi away

11 mi long · Easy · Dogs allowed · South Boston

Hiking Paved Dogs allowed

Melnea Cass Bike Path

2.0 mi away

0.9 mi long · Easy · Roxbury Crossing

Biking Paved

Boston HarborWalk

2.0 mi away

29 mi long · Easy · Dogs on leash · Boston Seaport

Hiking Biking Paved Wheelchair accessible Dogs allowed

Jazz Along the Charles

2.2 mi away

0.4 mi long · Easy · Dogs allowed · Back Bay

Hiking Biking Paved Dogs allowed

FROM DOCK

2.3 mi away

0.2 mi long · Boston Harbor Islands National Recreation Area

BUILDINGS

2.3 mi away

0.1 mi long · Boston Harbor Islands National Recreation Area

SW TRAIL

2.4 mi away

0.8 mi long · Boston Harbor Islands National Recreation Area

East Boston Greenway

2.4 mi away

2.3 mi long · Easy · East Boston

Hiking Biking Paved Greenway

NEWLY CLEARED

2.4 mi away

0.0 mi long · Boston Harbor Islands National Recreation Area

CAMPUS

2.4 mi away

0.0 mi long · Easy · Boston Harbor Islands National Recreation Area

Paved

Walking City Trail Section 4

2.4 mi away

6.5 mi long · Easy · Dogs allowed · Friends of the Public Garden

Hiking Paved Dogs allowed

Dr. Paul Dudley White Path

2.5 mi away

17 mi long · Easy · Dogs on leash · Lower Allston

Hiking Biking Paved Wheelchair accessible Dogs allowed

TO TOILET

2.6 mi away

0.0 mi long · Boston Harbor Islands National Recreation Area

FIELD EDGE

2.6 mi away

0.1 mi long · Boston Harbor Islands National Recreation Area

TO CAMP

2.6 mi away

0.0 mi long · Boston Harbor Islands National Recreation Area

Freedom Trail

2.7 mi away

0.3 mi long · Boston National Historical Park

Hiking Wheelchair accessible

Harborwalk Charlestown

3.1 mi away

1.9 mi long · VA Boston Healthcare System, Brockton Campus

Hiking

Quincy RiverWalk

3.4 mi away

2.6 mi long · Easy · Ashmont

Hiking Biking Paved

Somerville Community Path

3.5 mi away

3.0 mi long · Easy · Somerville

Hiking Biking Paved Wheelchair accessible

Walking City Trail Section 3

3.6 mi away

5.7 mi long · Easy · Dogs allowed · Mission Hill

Hiking Paved Wheelchair accessible Dogs allowed

Jamaicaway Bikepath

3.7 mi away

1.5 mi long · Easy · Back of the Hill

Hiking Biking Paved

Concrete Walk to Basement

3.9 mi away

0.0 mi long · Easy · John Fitzgerald Kennedy National Historic Site

Hiking Paved

Front Concrete Walkway

3.9 mi away

0.0 mi long · Easy · John Fitzgerald Kennedy National Historic Site

Hiking Paved

Southwest Side and Rear Yard Concrete Walkway

3.9 mi away

0.0 mi long · Easy · John Fitzgerald Kennedy National Historic Site

Hiking Paved

Pierre Lallement Bike Path

3.9 mi away

4.0 mi long · Easy · Roxbury Crossing

Hiking Biking Paved

Arborway

3.9 mi away

0.7 mi long · Easy · Jamaica Plain

Biking Paved

Neponset River Greenway

4.1 mi away

6.6 mi long · Easy · Milton Village

Hiking Biking Paved Greenway

Chelsea Greenway

4.3 mi away

0.7 mi long · Easy · Chelsea

Hiking Biking Paved Greenway

Deer Island Loop Trail

4.4 mi away

2.7 mi long · Easy · Winthrop

Hiking Biking Paved

Broadway

4.7 mi away

0.5 mi long · Everett

Biking Mountain biking

Walking City Trail Section 1

4.8 mi away

9.7 mi long · Easy · Clarendon Hills

Hiking Paved

Winthrop Greenway

4.9 mi away

0.6 mi long · Easy · Winthrop

Hiking Biking Paved Greenway

Wellington Greenway

5.0 mi away

0.6 mi long · Easy · Ten Hills

Hiking Biking Paved Greenway

Mill Creek Riverwalk

5.0 mi away

0.7 mi long · Easy · Dogs on leash · Revere

Hiking Paved Dogs allowed

Walking City Trail Section 2

5.2 mi away

5.6 mi long · Moderate · Jamaica Plain

Hiking Paved

Everett Riverwalk

5.3 mi away

1.1 mi long · Malden

Hiking Biking Mountain biking

Methane trench

5.8 mi away

1.0 mi long · West Somerville/Davis Square

Hiking

Fresh Pond Path

6.0 mi away

2.5 mi long · Easy · North Brighton

Hiking Biking Paved

Quarry Trail

6.1 mi away

0.7 mi long · Milton

Hiking

Clippership Connector

6.2 mi away

0.5 mi long · Easy · Medford

Hiking Biking Paved

BOARDWALK

6.2 mi away

0.0 mi long · Easy · Boston Harbor Islands National Recreation Area

Paved

STEPS

6.2 mi away

0.0 mi long · Easy · Boston Harbor Islands National Recreation Area

Paved

Alewife Brook Parkway Path

6.3 mi away

0.6 mi long · Easy · West Somerville/Davis Square

Hiking Biking Paved

Blue Trail

6.3 mi away

0.9 mi long · Chestnut Hill

Hiking

BATTERY

6.4 mi away

0.0 mi long · Easy · Boston Harbor Islands National Recreation Area

Paved

Alewife Linear Park

6.4 mi away

2.1 mi long · Easy · West Somerville/Davis Square

Hiking Biking Paved

Alewife Brook Greenway

6.6 mi away

2.5 mi long · Easy · Tufts University

Hiking Biking Paved Greenway

MAIN

6.6 mi away

1.4 mi long · Boston Harbor Islands National Recreation Area

Red Trail

6.6 mi away

0.9 mi long · Thompsonville

Hiking

W/STEPS

6.6 mi away

0.0 mi long · Easy · Boston Harbor Islands National Recreation Area

Paved

Quarries Foot Path

6.7 mi away

0.6 mi long · Easy · Quincy

Hiking

Sawcut Notch Path

6.8 mi away

1.4 mi long · Easy · Milton

Hiking Paved

Crags Foot Path

6.8 mi away

0.9 mi long · Easy · Milton

Hiking Paved

Green Trail

6.9 mi away

0.9 mi long · Thompsonville

Hiking

Watertown-Cambridge Greenway

6.9 mi away

2.7 mi long · Easy · Faneuil

Hiking Biking Paved Greenway

Skyline Trail

7.0 mi away

9.3 mi long · Easy · Milton Center

Hiking Paved

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Nearby cities

All trails in Massachusetts

Common questions

How many trails are near South Boston?
We list 1,076 trails within 30 miles of South Boston, Massachusetts. This page shows the 60 closest.
What is the longest trail near South Boston?
Boston HarborWalk is the longest on this page at about 29 miles, 2.0 miles from South Boston.
Are there dog-friendly trails near South Boston?
Yes. Map data lists 10 trails on this page as open to dogs, including South Bay Harbor Trail, South Bay Harbor Trail, Lagoon Path. Most trails have no dog rule in our data yet, so check signs at the trailhead.