Blue Trail
0.5 mi away0.9 mi long · Chestnut Hill
Hiking
Trails near Chestnut Hill, MA
1,201 trails within 30 miles of Chestnut Hill, for hiking, biking, horseback riding and off-road riding. Tap a trail for its map, trailhead and directions.
Hiking trails (1,137) Walking trails (1,106) Bike trails (395) Mountain bike trails (306) Paved trails (164) Horse trails (74) ATV and UTV trails (3) Dirt bike trails (8) Off-road and 4x4 trails (3) Dog-friendly trails (25) Snowmobile trails (22) Cross-country ski trails (15) Wheelchair-accessible trails (17) Rail trails (22) Greenways (18)
Quick picks
- Closest: Blue Trail 0.9 mi, 0.5 mi away
- Longest: Dr. Paul Dudley White Path 17 mi, 4.8 mi away
- Easy walk: Sudbury Aqueduct Trail 1.3 mi, 2.1 mi away
- Paved: Watertown-Cambridge Greenway 2.7 mi, 2.5 mi away
- Dog friendly: Walking City Trail Section 3 5.7 mi, 2.7 mi away
- Mountain biking: Blue Heron Trail 2.8 mi, 3.6 mi away
All nearby trails
Red Trail
0.8 mi away0.9 mi long · Thompsonville
Hiking
Green Trail
0.9 mi away0.9 mi long · Thompsonville
Hiking
Sudbury Aqueduct Trail
2.1 mi away1.3 mi long · Newton Highlands
Hiking
Watertown-Cambridge Greenway
2.5 mi away2.7 mi long · Easy · Faneuil
Hiking Biking Paved Greenway
0.0 mi long · Easy · John Fitzgerald Kennedy National Historic Site
Hiking Paved
Front Concrete Walkway
2.5 mi away0.0 mi long · Easy · John Fitzgerald Kennedy National Historic Site
Hiking Paved
Concrete Walk to Basement
2.5 mi away0.0 mi long · Easy · John Fitzgerald Kennedy National Historic Site
Hiking Paved
Walking City Trail Section 3
2.7 mi away5.7 mi long · Easy · Dogs allowed · Mission Hill
Hiking Paved Wheelchair accessible Dogs allowed
Jamaicaway Bikepath
2.7 mi away1.5 mi long · Easy · Back of the Hill
Hiking Biking Paved
Upper Falls Greenway
2.9 mi away1.1 mi long · Newton Upper Falls
Biking Mountain biking Greenway
Watertown Community Path
3.0 mi away0.7 mi long · Easy · Watertown
Hiking Biking Paved
Blue Heron Trail
3.1 mi away0.9 mi long · Newton Upper Falls
Hiking Biking Mountain biking
Cochituate Aqueduct Trail
3.1 mi away1.3 mi long · Newton Upper Falls
Hiking Biking Mountain biking
Pierre Lallement Bike Path
3.3 mi away4.0 mi long · Easy · Roxbury Crossing
Hiking Biking Paved
Healthy Heart Trail
3.4 mi away1.2 mi long · Needham
Hiking Biking Mountain biking
Arborway
3.4 mi away0.7 mi long · Easy · Jamaica Plain
Biking Paved
Fresh Pond Path
3.5 mi away2.5 mi long · Easy · North Brighton
Hiking Biking Paved
Walking City Trail Section 2
3.6 mi away5.6 mi long · Moderate · Jamaica Plain
Hiking Paved
Blue Heron Trail
3.6 mi away2.8 mi long · Oak Hill Park
Hiking Biking Mountain biking
Blue Heron Trail
3.6 mi away0.9 mi long · Oak Hill Park
Hiking Biking Mountain biking
Charles River Path
3.7 mi away4.7 mi long · Easy · Bemis
Hiking Biking Paved
Cochituate Aqueduct Trail
4.0 mi away0.8 mi long · Newton Lower Falls
Hiking
Melnea Cass Bike Path
4.0 mi away0.9 mi long · Easy · Roxbury Crossing
Biking Paved
Sudbury Aqueduct Trail
4.1 mi away0.5 mi long · Easy · Newton Upper Falls
Hiking Biking Mountain biking
Walking City Trail Section 4
4.2 mi away6.5 mi long · Easy · Dogs allowed · Friends of the Public Garden
Hiking Paved Dogs allowed
Methane trench
4.2 mi away1.0 mi long · West Somerville/Davis Square
Hiking
Blue Heron Trail
4.4 mi away1.8 mi long · Easy · Oak Hill Park
Hiking Biking Paved
Charles River Path
4.5 mi away0.9 mi long · Newton Lower Falls
Hiking Biking Mountain biking
Esker Trail
4.6 mi away0.8 mi long · Newton Lower Falls
Hiking
Alewife Brook Parkway Path
4.6 mi away0.6 mi long · Easy · West Somerville/Davis Square
Hiking Biking Paved
Coal Road
4.6 mi away0.8 mi long · Easy · Belmont
Hiking Biking Mountain biking
Riverwalk
4.6 mi away0.5 mi long · Easy · Waltham
Hiking Biking Paved
Jazz Along the Charles
4.6 mi away0.4 mi long · Easy · Dogs allowed · Back Bay
Hiking Biking Paved Dogs allowed
Longfellow Pond Trail
4.7 mi away0.7 mi long · Newton Lower Falls
Hiking
Alewife Linear Park
4.7 mi away2.1 mi long · Easy · West Somerville/Davis Square
Hiking Biking Paved
South Bay Harbor Trail
4.8 mi away2.5 mi long · Easy · Dogs on leash · South Boston
Hiking Biking Paved Wheelchair accessible Dogs allowed
Keller Loop
4.8 mi away0.7 mi long · Dedham
Hiking
Dr. Paul Dudley White Path
4.8 mi away17 mi long · Easy · Dogs on leash · Lower Allston
Hiking Biking Paved Wheelchair accessible Dogs allowed
Western Greenway
4.8 mi away7.4 mi long · Hard · Belmont
Hiking Biking Mountain biking Greenway
Alewife Brook Greenway
4.8 mi away2.5 mi long · Easy · Tufts University
Hiking Biking Paved Greenway
Highland Farm Loop
5.0 mi away0.7 mi long · No dogs · Belmont
Hiking
Crosstown Trail
5.0 mi away1.1 mi long · Newton Lower Falls
Hiking
Centennial Park Trail
5.1 mi away0.9 mi long · Newton Lower Falls
Hiking
Sudbury Path
5.2 mi away1.0 mi long · Easy · Newton Lower Falls
Hiking Biking Mountain biking
Lagoon Path
5.2 mi away0.5 mi long · Easy · Dogs on leash · Friends of the Public Garden
Hiking Paved Wheelchair accessible Dogs allowed
Blue Blazed Trail
5.2 mi away1.8 mi long · Dedham
Hiking Biking Mountain biking
Somerville Community Path
5.3 mi away3.0 mi long · Easy · Somerville
Hiking Biking Paved Wheelchair accessible
Goat Track
5.4 mi away1.2 mi long · Weston Ski Track
Hiking Cross-country skiing
South Bay Harbor Trail
5.5 mi away0.5 mi long · Easy · Dogs on leash · South Boston
Hiking Biking Paved Wheelchair accessible Dogs allowed
Ring Path
5.5 mi away0.5 mi long · Arlington
Hiking Biking Mountain biking
Pine Springs Trail
5.6 mi away0.5 mi long · Easy · Waltham
Hiking
Brook Path
5.7 mi away0.2 mi long · Easy · Wellesley
Hiking Biking Paved
Carriage Road
5.7 mi away0.9 mi long · Easy · Belmont
Hiking Biking Mountain biking
Green Trail
5.9 mi away0.5 mi long · Needham
Hiking Biking Mountain biking
Walking City Trail Section 1
6.0 mi away9.7 mi long · Easy · Clarendon Hills
Hiking Paved
Yellow Triangle
6.0 mi away6.8 mi long · Moderate · Needham
Hiking Biking Paved
Blue Trail
6.0 mi away0.6 mi long · Needham
Biking Mountain biking
Crosstown Trail
6.1 mi away0.6 mi long · Wellesley
Hiking Biking Mountain biking
0.3 mi long · Easy · Boston
Hiking Paved
Nearby cities
Common questions
- How many trails are near Chestnut Hill?
- We list 1,201 trails within 30 miles of Chestnut Hill, Massachusetts. This page shows the 60 closest.
- What is the longest trail near Chestnut Hill?
- Dr. Paul Dudley White Path is the longest on this page at about 17 miles, 4.8 miles from Chestnut Hill.
- Are there dog-friendly trails near Chestnut Hill?
- Yes. Map data lists 7 trails on this page as open to dogs, including Walking City Trail Section 3, Walking City Trail Section 4, Jazz Along the Charles. Most trails have no dog rule in our data yet, so check signs at the trailhead.