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Trails near Cheshire, CT

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

Hiking trails (894) Walking trails (881) Bike trails (155) Mountain bike trails (79) Paved trails (113) Horse trails (71) ATV and UTV trails (3) Off-road and 4x4 trails (4) Dog-friendly trails (29) Snowmobile trails (4) Cross-country ski trails (36) Wheelchair-accessible trails (6) Rail trails (3) Greenways (22)

Quick picks

All nearby trails

New Haven & Northampton Canal Greenway

0.7 mi away

10 mi long · Easy · Cheshire Village

Hiking Biking Paved Greenway

Brooke Yellow Trail

1.9 mi away

0.3 mi long · Cheshire

Hiking

Brooke Blue Trail

2.0 mi away

1.0 mi long · Cheshire

Hiking

Roaring Brook Falls Trail

2.2 mi away

0.6 mi long · Cheshire

Hiking

Green Trail

2.6 mi away

0.2 mi long · Cheshire

Hiking

Red Trail

2.6 mi away

1.4 mi long · Cheshire

Hiking

Purple Trail

2.6 mi away

0.3 mi long · Cheshire

Hiking

Yellow Trail

2.6 mi away

0.9 mi long · Cheshire

Hiking

Blue Trail

2.9 mi away

0.6 mi long · Cheshire

Hiking

Quinnipiac River Gorge Trail

3.0 mi away

2.5 mi long · Easy · Meriden

Hiking Biking Paved

Black Trail

3.0 mi away

0.2 mi long · Cheshire

Hiking

Brooksvale Park Path

3.1 mi away

0.3 mi long · Easy · Cheshire

Hiking Biking Paved

Ives Yellow Trail

3.5 mi away

0.5 mi long · Cheshire Village

Hiking

Ives Red Trail

3.6 mi away

0.3 mi long · Cheshire Village

Hiking

Ives Blue Trail

3.6 mi away

1.1 mi long · Meriden

Hiking

Horse Trail

3.9 mi away

2.5 mi long · Hamden

Hiking Horses

Riverbound Orange Trail

4.0 mi away

0.7 mi long · Cheshire Village

Hiking

Riverbound Blue Trail

4.0 mi away

0.3 mi long · Cheshire Village

Hiking

Horse Trail

4.0 mi away

3.6 mi long · Connecticut Department of Energy and Environmental Protection

Hiking Horses

Riverbound Red Trail

4.0 mi away

0.2 mi long · Cheshire Village

Hiking

Black Trail

4.0 mi away

1.2 mi long · Prospect

Hiking

Yellow Trail

4.0 mi away

0.7 mi long · Prospect

Hiking

White Trail

4.1 mi away

0.3 mi long · Prospect

Hiking

Quinnipiac Connector Trail

4.1 mi away

1.6 mi long · Easy · Dogs allowed · Prospect

Hiking Dogs allowed

Orange Trail

4.2 mi away

0.6 mi long · Prospect

Hiking

Dark Green Trail

4.2 mi away

0.6 mi long · Prospect

Hiking

Lost Vista Trail

4.2 mi away

0.3 mi long · Hamden

Hiking

Quinnipiac Linear Trail

4.2 mi away

2.1 mi long · Easy · Wallingford

Hiking Biking Paved

Red Trail

4.2 mi away

2.4 mi long · Prospect

Hiking

Blue Trail

4.2 mi away

0.4 mi long · Cheshire Village

Hiking

Ski Trail

4.5 mi away

2.8 mi long · Connecticut Department of Energy and Environmental Protection

Hiking

Tower Trail

4.7 mi away

1.5 mi long · Connecticut Department of Energy and Environmental Protection

Hiking

Judge Cook's Oxen Trail

5.1 mi away

0.3 mi long · Hamden

Hiking

Dickerman Carriage Road

5.2 mi away

0.6 mi long · Hamden

Hiking

Nature Trail

5.3 mi away

1.1 mi long · Connecticut Department of Energy and Environmental Protection

Hiking

New Haven & Northampton Canal Greenway

5.4 mi away

5.8 mi long · Easy · Hamden

Hiking Biking Paved Greenway

Finch Brook Trail

6.0 mi away

2.5 mi long · Wolcott

Hiking

Beacon Cap Trail

6.1 mi away

0.3 mi long · Connecticut Forest and Park Association

Hiking

Quinnipiac Trail

6.3 mi away

20 mi long · Moderate · Dogs allowed · Connecticut Forest and Park Association

Hiking Dogs allowed

Red Trail

6.3 mi away

1.2 mi long · Hamden

Hiking

Naugatuck Trail

6.7 mi away

5.3 mi long · Connecticut Forest and Park Association

Hiking

Whittemore Trail

6.7 mi away

0.7 mi long · Connecticut Forest and Park Association

Hiking

Hein Hiking Trail

6.7 mi away

0.7 mi long · Bethany Land Trust

Hiking

Hein Horse Trail

6.7 mi away

0.6 mi long · Bethany Land Trust

Horses

Sanford Feeder

6.8 mi away

0.6 mi long · Hamden

Hiking

Cedar Meadows Trail

6.8 mi away

0.3 mi long · Bethany Land Trust

Hiking Horses

Carol and Polly's Path

6.9 mi away

0.3 mi long · Bethany Land Trust

Hiking

Tibby's Trail

7.0 mi away

0.6 mi long · Naugatuck

Hiking

Northrop Road Trail

7.0 mi away

0.5 mi long · Naugatuck

Hiking

Old Metacomet

7.1 mi away

0.5 mi long · Meriden

Hiking

Banton Quinnipiac Trail

7.1 mi away

2.7 mi long · North Haven

Hiking

Van Epps Trail

7.1 mi away

0.4 mi long · Naugatuck

Hiking

Woodward Trail

7.1 mi away

0.8 mi long · Naugatuck

Hiking

Grobe Green Gadabout Trail

7.3 mi away

0.3 mi long · Naugatuck

Hiking

Blue-Red

7.5 mi away

1.0 mi long · Wallingford Center

Hiking

Yellow

7.5 mi away

0.7 mi long · Wallingford Center

Hiking

Beaver Trail

7.5 mi away

0.6 mi long · Naugatuck

Hiking

White Birches Trail

7.5 mi away

0.5 mi long · Naugatuck

Hiking

Black-White

7.6 mi away

0.3 mi long · Wallingford Center

Hiking

Orange

7.6 mi away

1.4 mi long · Wallingford Center

Hiking

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Nearby cities

All trails in Connecticut

Common questions

How many trails are near Cheshire?
We list 903 trails within 30 miles of Cheshire, Connecticut. This page shows the 60 closest.
What is the longest trail near Cheshire?
Quinnipiac Trail is the longest on this page at about 20 miles, 6.3 miles from Cheshire.
Are there dog-friendly trails near Cheshire?
Yes. Map data lists 2 trails on this page as open to dogs, including Quinnipiac Connector Trail, Quinnipiac Trail. Most trails have no dog rule in our data yet, so check signs at the trailhead.