27 Trails in Cheshire, Connecticut

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

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