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Trails near Jamaica Plain, MA

1,182 trails within 30 miles of Jamaica Plain, for hiking, biking, horseback riding and off-road riding. Tap a trail for its map, trailhead and directions.

Hiking trails (1,118) Walking trails (1,089) Bike trails (396) Mountain bike trails (308) Paved trails (161) Horse trails (71) ATV and UTV trails (3) Dirt bike trails (6) Off-road and 4x4 trails (3) Dog-friendly trails (27) Snowmobile trails (21) Cross-country ski trails (14) Wheelchair-accessible trails (16) Rail trails (22) Greenways (18)

Quick picks

All nearby trails

Jamaicaway Bikepath

0.4 mi away

1.5 mi long · Easy · Back of the Hill

Hiking Biking Paved

Walking City Trail Section 3

0.6 mi away

5.7 mi long · Easy · Dogs allowed · Mission Hill

Hiking Paved Wheelchair accessible Dogs allowed

Pierre Lallement Bike Path

0.6 mi away

4.0 mi long · Easy · Roxbury Crossing

Hiking Biking Paved

Arborway

0.7 mi away

0.7 mi long · Easy · Jamaica Plain

Biking Paved

Walking City Trail Section 2

1.7 mi away

5.6 mi long · Moderate · Jamaica Plain

Hiking Paved

Melnea Cass Bike Path

2.5 mi away

0.9 mi long · Easy · Roxbury Crossing

Biking Paved

Concrete Walk to Basement

2.6 mi away

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

Hiking Paved

Southwest Side and Rear Yard Concrete Walkway

2.6 mi away

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

Hiking Paved

Front Concrete Walkway

2.6 mi away

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

Hiking Paved

South Bay Harbor Trail

2.9 mi away

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

Hiking Biking Paved Wheelchair accessible Dogs allowed

Blue Trail

2.9 mi away

0.9 mi long · Chestnut Hill

Hiking

Red Trail

3.1 mi away

0.9 mi long · Thompsonville

Hiking

Walking City Trail Section 4

3.3 mi away

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

Hiking Paved Dogs allowed

Walking City Trail Section 1

3.4 mi away

9.7 mi long · Easy · Clarendon Hills

Hiking Paved

Green Trail

3.5 mi away

0.9 mi long · Thompsonville

Hiking

Jazz Along the Charles

3.7 mi away

0.4 mi long · Easy · Dogs allowed · Back Bay

Hiking Biking Paved Dogs allowed

South Bay Harbor Trail

3.9 mi away

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

Hiking Biking Paved Wheelchair accessible Dogs allowed

Neponset River Greenway

3.9 mi away

6.6 mi long · Easy · Milton Village

Hiking Biking Paved Greenway

Lagoon Path

4.0 mi away

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

Hiking Paved Wheelchair accessible Dogs allowed

Dr. Paul Dudley White Path

4.0 mi away

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

Hiking Biking Paved Wheelchair accessible Dogs allowed

Blue Heron Trail

4.3 mi away

2.8 mi long · Oak Hill Park

Hiking Biking Mountain biking

Sudbury Aqueduct Trail

4.6 mi away

1.3 mi long · Newton Highlands

Hiking

Keller Loop

4.7 mi away

0.7 mi long · Dedham

Hiking

Blue Heron Trail

4.7 mi away

1.8 mi long · Easy · Oak Hill Park

Hiking Biking Paved

Healthy Heart Trail

4.8 mi away

1.2 mi long · Needham

Hiking Biking Mountain biking

Watertown-Cambridge Greenway

4.8 mi away

2.7 mi long · Easy · Faneuil

Hiking Biking Paved Greenway

Blue Heron Trail

4.9 mi away

0.9 mi long · Oak Hill Park

Hiking Biking Mountain biking

Upper Falls Greenway

4.9 mi away

1.1 mi long · Newton Upper Falls

Biking Mountain biking Greenway

Washington-Rochambeau Revolutionary Route National Historic Trail

4.9 mi away

0.3 mi long · Easy · Boston

Hiking Paved

Blue Heron Trail

4.9 mi away

0.9 mi long · Newton Upper Falls

Hiking Biking Mountain biking

Proposed Dedham Heritage Rail Trail

4.9 mi away

0.9 mi long · Dedham

Hiking Rail trail

Somerville Community Path

5.0 mi away

3.0 mi long · Easy · Somerville

Hiking Biking Paved Wheelchair accessible

Boston Boundless Trail Section 1

5.0 mi away

11 mi long · Easy · Dogs allowed · South Boston

Hiking Paved Dogs allowed

Dedham Heritage Rail Trail

5.0 mi away

0.5 mi long · Readville

Biking Mountain biking Rail trail

Fresh Pond Path

5.1 mi away

2.5 mi long · Easy · North Brighton

Hiking Biking Paved

Quincy RiverWalk

5.1 mi away

2.6 mi long · Easy · Ashmont

Hiking Biking Paved

Neponset River Greenway

5.1 mi away

1.1 mi long · Easy · Readville

Hiking Biking Paved Greenway

SW TRAIL

5.4 mi away

0.8 mi long · Boston Harbor Islands National Recreation Area

Freedom Trail

5.4 mi away

0.3 mi long · Boston National Historical Park

Hiking Wheelchair accessible

Methane trench

5.4 mi away

1.0 mi long · West Somerville/Davis Square

Hiking

Blue Blazed Trail

5.4 mi away

1.8 mi long · Dedham

Hiking Biking Mountain biking

Cochituate Aqueduct Trail

5.5 mi away

1.3 mi long · Newton Upper Falls

Hiking Biking Mountain biking

Watertown Community Path

5.5 mi away

0.7 mi long · Easy · Watertown

Hiking Biking Paved

FROM DOCK

5.7 mi away

0.2 mi long · Boston Harbor Islands National Recreation Area

East Boston Greenway

5.7 mi away

2.3 mi long · Easy · East Boston

Hiking Biking Paved Greenway

BUILDINGS

5.7 mi away

0.1 mi long · Boston Harbor Islands National Recreation Area

Boston HarborWalk

5.8 mi away

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

Hiking Biking Paved Wheelchair accessible Dogs allowed

Quarry Trail

5.8 mi away

0.7 mi long · Milton

Hiking

CAMPUS

5.8 mi away

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

Paved

NEWLY CLEARED

5.9 mi away

0.0 mi long · Boston Harbor Islands National Recreation Area

Alewife Brook Parkway Path

5.9 mi away

0.6 mi long · Easy · West Somerville/Davis Square

Hiking Biking Paved

Harborwalk Charlestown

5.9 mi away

1.9 mi long · VA Boston Healthcare System, Brockton Campus

Hiking

Chestnut Run Path

5.9 mi away

0.6 mi long · Moderate · Milton Center

Hiking Biking Mountain biking

Sudbury Aqueduct Trail

6.1 mi away

0.5 mi long · Easy · Newton Upper Falls

Hiking Biking Mountain biking

Sawcut Notch Path

6.1 mi away

1.4 mi long · Easy · Milton

Hiking Paved

FIELD EDGE

6.1 mi away

0.1 mi long · Boston Harbor Islands National Recreation Area

Alewife Linear Park

6.1 mi away

2.1 mi long · Easy · West Somerville/Davis Square

Hiking Biking Paved

TO TOILET

6.1 mi away

0.0 mi long · Boston Harbor Islands National Recreation Area

TO CAMP

6.2 mi away

0.0 mi long · Boston Harbor Islands National Recreation Area

Alewife Brook Greenway

6.3 mi away

2.5 mi long · Easy · Tufts University

Hiking Biking Paved Greenway

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Nearby cities

All trails in Massachusetts

Common questions

How many trails are near Jamaica Plain?
We list 1,182 trails within 30 miles of Jamaica Plain, Massachusetts. This page shows the 60 closest.
What is the longest trail near Jamaica Plain?
Boston HarborWalk is the longest on this page at about 29 miles, 5.8 miles from Jamaica Plain.
Are there dog-friendly trails near Jamaica Plain?
Yes. Map data lists 9 trails on this page as open to dogs, including Walking City Trail Section 3, South Bay Harbor Trail, Walking City Trail Section 4. Most trails have no dog rule in our data yet, so check signs at the trailhead.