27 Trails in Cheshire, Connecticut

Trail Name Difficulty Length (mi) Rating City
Brooksvale Park And Naugatuck State Forest Advanced 10.0 ** Hamden
Cheshire Lock 12 Easiest 18.0 ***** Cheshire
Crescent Lake Intermediate 6 **** Southington
East Rock Park Intermediate 5.0 ***** New Haven
Farmington Canal Heritage Trail Easiest 5.0 * Hamden
Genesee Recreation Area Beginner 10.0 *** Madison
Larkin State Bridal Trail Easiest 10.0 **** Southbury
Middlebury Greenway Easiest 10.0 **** Middlebury
Millers Pond Advanced 5.0 ***** Durham
Nassahegan State Forest Intermediate 15.0 ***** Burlington
Powder Ridge Bike Park Intermediate 0 *** Middlefield
Racebrook Tract 11.0 *** Middletown
Rockhouse Hill Sanctuary Intermediate 12.0 ***** Oxford
Rockland Preserve Intermediate 25.0 **** Madison
Rockwell Park 0 Bristol
Sessions Woods 20.0 *** Burlington
Stony Creek Quarry Preserve Intermediate 10.0 *** Branford
Supply Ponds Intermediate 10.0 *** Branford
Thomaston Dam Easiest 0.0 *** Thomaston
Timberlands 5.0 Madison
Tyler Mills Intermediate 10.0 *** Wallingford
Wadsworth State Park Intermediate 5.0 **** Middletown
West Hartford Reservoir Intermediate 10.0 **** West Hartford
West Rocks State Park Intermediate 12.0 *** New Haven
Westwoods Intermediate 30.0 **** Guilford
Winding Trails Beginner 5.0 *** Farmington
Yale Preserve 6.0 Woodbridge