How many trails are near Pittsfield?

We list 694 trails within 30 miles of Pittsfield, Massachusetts. This page shows the 60 closest.

What is the longest trail near Pittsfield?

October Mountain Loop Trail is the longest on this page at about 6.5 miles, 5.4 miles from Pittsfield.

Are there dog-friendly trails near Pittsfield?

None of the trails on this page have a dog rule in our data yet. Check signs at the trailhead or the park's website.

Trails near Pittsfield, MA

694 trails within 30 miles of Pittsfield, for hiking, biking, horseback riding and off-road riding. Tap a trail for its map, trailhead and directions.

Hiking trails (639) Walking trails (613) Bike trails (121) Mountain bike trails (101) Paved trails (40) Horse trails (13) ATV and UTV trails (7) Off-road and 4x4 trails (8) Dog-friendly trails (13) Snowmobile trails (16) Cross-country ski trails (31) Wheelchair-accessible trails (14) Rail trails (7) Greenways (4)

Quick picks

Closest: Downtown Loop 2.0 mi, 0.5 mi away
Longest: October Mountain Loop Trail 6.5 mi, 5.4 mi away
Easy walk: Downtown Loop 2.0 mi, 0.5 mi away
Paved: Downtown Loop 2.0 mi, 0.5 mi away
ATV / dirt bike: Schemerhorn Trail 1.7 mi, 5.4 mi away

All nearby trails

Downtown Loop

0.5 mi away

2.0 mi long · Easy · Pittsfield

Hiking Paved

Sacred Way Trail

1.5 mi away

0.9 mi long · Pittsfield

Hiking

Wolf Pine Trail

1.6 mi away

0.5 mi long · Pittsfield

Hiking

Wild Acres Park

2.3 mi away

0.8 mi long · Pittsfield

Hiking

Mahanna Cobble Trail

2.8 mi away

1.3 mi long · Pittsfield

Hiking

Blue Trail

2.8 mi away

0.8 mi long · Dalton

Hiking Biking Mountain biking

Red Trail

3.4 mi away

1.2 mi long · Dalton

Hiking Biking Mountain biking

Blue Trail

3.4 mi away

0.5 mi long · Dalton

Hiking Biking Mountain biking

Beaver Tail Trail

3.4 mi away

0.7 mi long · Pittsfield

Hiking

Unverified DCR Track

3.5 mi away

1.9 mi long · Pittsfield

Hiking

Unverified DCR Track

3.6 mi away

0.9 mi long · Pittsfield

Hiking

Bear Claw

3.7 mi away

1.2 mi long · Pittsfield

Hiking

Red Trail

3.7 mi away

0.9 mi long · Dalton

Hiking Biking Mountain biking

Deer Hill

3.8 mi away

1.2 mi long · Pittsfield

Hiking

Vosburgh CC Trail

3.8 mi away

0.9 mi long · Pittsfield

Green Trail

3.8 mi away

1.4 mi long · Dalton

Hiking

Honey Bear

3.9 mi away

0.7 mi long · Pittsfield

Hiking

Parker Brook Trail

4.0 mi away

1.3 mi long · Pittsfield

Honwee Loop Trail

4.1 mi away

3.1 mi long · Lanesborough

Hiking

Balance Rock Trail

4.3 mi away

0.7 mi long · Lanesborough

Upper Rollercoaster

4.4 mi away

0.8 mi long · Pittsfield

Hiking

Ghost Ski Trail

4.4 mi away

0.5 mi long · Pittsfield

Burgoyne Trail

4.5 mi away

1.4 mi long · Lanesborough

Daniels Brook Trail

4.5 mi away

1.4 mi long · Lanesborough

Shadow Ski Trail

4.6 mi away

0.6 mi long · Pittsfield

Ten-Point Buck

4.6 mi away

0.5 mi long · Easy · Lanesborough

Hiking Paved

Hawthorne trail

4.6 mi away

0.8 mi long · Pittsfield

West Mountain Trail

4.7 mi away

1.4 mi long · Pittsfield

Hiking

Circuit Trail

4.7 mi away

0.9 mi long · Pittsfield

Hiking

Turner Trail

4.8 mi away

0.7 mi long · Pittsfield

Shaker Brook Trail

4.8 mi away

1.4 mi long · Richmond

Hermit Thrush Loop

4.8 mi away

0.8 mi long · Lenox

Hiking

CCC Trail

4.9 mi away

2.4 mi long · Richmond

Balance Rock Loop Trail

4.9 mi away

1.7 mi long · Lanesborough

Balance Rock Trail

4.9 mi away

1.0 mi long · Lanesborough

Doll Mountain Trail

4.9 mi away

1.1 mi long · Richmond

Shaker Mountain Trail

4.9 mi away

2.6 mi long · Richmond

Hiking

North Family Trail

5.0 mi away

1.0 mi long · Richmond

Hiking

Roaring Brook Trail

5.0 mi away

1.2 mi long · Pittsfield

Hiking

North Branch Trail

5.0 mi away

0.7 mi long · Pittsfield

Taconic Skyline Trail

5.1 mi away

3.2 mi long · Lanesborough

Log Hop

5.1 mi away

1.4 mi long · Lenox

Hiking Biking Mountain biking

Honolulu

5.1 mi away

2.8 mi long · Lanesborough

Hiking

Constitution Hill Trail

5.1 mi away

1.6 mi long · Lanesborough

Hiking

Smith Mountain Trail

5.1 mi away

0.6 mi long · Pittsfield

Woolsey

5.1 mi away

0.6 mi long · Lenox

Hiking Biking Mountain biking

Overbrook Trail

5.2 mi away

0.9 mi long · Lenox

Hiking

Yokun Ridge Trail

5.2 mi away

2.7 mi long · Lenox

Hiking

Brickhouse Mountain Trail

5.2 mi away

1.2 mi long · Pittsfield

Pine Mountain Trail

5.2 mi away

1.9 mi long · Pittsfield

Aspinwall

5.3 mi away

0.8 mi long · Lenox

Hiking Biking Mountain biking

Coakley/Main

5.4 mi away

1.6 mi long · Lenox

Hiking Biking Mountain biking

October Mountain Loop Trail

5.4 mi away

6.5 mi long · Lenox

Hiking

Quicksand Trail

5.4 mi away

0.9 mi long · Lee

Hiking

Roaring Brook Trail

5.4 mi away

0.5 mi long · Lenox

Hiking

Schemerhorn Trail

5.4 mi away

1.7 mi long · Lenox

Hiking Biking Mountain biking ATV / UTV

Taconic Skyline Trail

5.5 mi away

1.9 mi long · Pittsfield

Laurel Trail

5.5 mi away

0.8 mi long · Lenox

Hiking

Trail of the Ledges

5.5 mi away

1.0 mi long · Lenox

Hiking

Lulu Brook Trail

5.5 mi away

1.4 mi long · Lanesborough

Hiking

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Nearby cities

All trails in Massachusetts

Common questions

How many trails are near Pittsfield?: We list 694 trails within 30 miles of Pittsfield, Massachusetts. This page shows the 60 closest.
What is the longest trail near Pittsfield?: October Mountain Loop Trail is the longest on this page at about 6.5 miles, 5.4 miles from Pittsfield.
Are there dog-friendly trails near Pittsfield?: None of the trails on this page have a dog rule in our data yet. Check signs at the trailhead or the park's website.