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Walking trails near Brookline, MA

1,075 walking trails within 30 miles of Brookline. Tap a trail for its map, trailhead and directions.

5.7 mi long · Easy · Dogs allowed · Mission Hill

Hiking Paved Wheelchair accessible Dogs allowed

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

Hiking Paved

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

Hiking Paved

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

Hiking Paved

1.5 mi long · Easy · Back of the Hill

Hiking Biking Paved

4.0 mi long · Easy · Roxbury Crossing

Hiking Biking Paved

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

Hiking Paved Dogs allowed

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

Hiking Biking Paved Wheelchair accessible Dogs allowed

0.4 mi long · Easy · Dogs allowed · Back Bay

Hiking Biking Paved Dogs allowed

Blue Trail

2.7 mi away

0.9 mi long · Chestnut Hill

Hiking

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

Hiking Biking Paved Wheelchair accessible Dogs allowed

Red Trail

3.0 mi away

0.9 mi long · Thompsonville

Hiking

Lagoon Path

3.0 mi away

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

Hiking Paved Wheelchair accessible Dogs allowed

5.6 mi long · Moderate · Jamaica Plain

Hiking Paved

Green Trail

3.2 mi away

0.9 mi long · Thompsonville

Hiking

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

Hiking Biking Paved Wheelchair accessible Dogs allowed

Fresh Pond Path

3.6 mi away

2.5 mi long · Easy · North Brighton

Hiking Biking Paved

3.0 mi long · Easy · Somerville

Hiking Biking Paved Wheelchair accessible

2.7 mi long · Easy · Faneuil

Hiking Biking Paved Greenway

Methane trench

3.9 mi away

1.0 mi long · West Somerville/Davis Square

Hiking

0.3 mi long · Easy · Boston

Hiking Paved

11 mi long · Easy · Dogs allowed · South Boston

Hiking Paved Dogs allowed

Freedom Trail

4.3 mi away

0.3 mi long · Boston National Historical Park

Hiking Wheelchair accessible

1.3 mi long · Newton Highlands

Hiking

0.6 mi long · Easy · West Somerville/Davis Square

Hiking Biking Paved

0.7 mi long · Easy · Watertown

Hiking Biking Paved

2.1 mi long · Easy · West Somerville/Davis Square

Hiking Biking Paved

9.7 mi long · Easy · Clarendon Hills

Hiking Paved

2.5 mi long · Easy · Tufts University

Hiking Biking Paved Greenway

2.3 mi long · Easy · East Boston

Hiking Biking Paved Greenway

Nearby cities

Walking trails in Massachusetts

Common questions

How many walking trails are near Brookline?
We list 1,075 walking trails within 30 miles of Brookline, Massachusetts. This page shows the 30 closest.
What is the longest walking trail near Brookline?
Dr. Paul Dudley White Path is the longest on this page at about 17 miles, 2.8 miles from Brookline.
Are there dog-friendly trails near Brookline?
Yes. Map data lists 8 trails on this page as open to dogs, including Walking City Trail Section 3, Walking City Trail Section 4, South Bay Harbor Trail. Most trails have no dog rule in our data yet, so check signs at the trailhead.