44 Trails in Middletown, Connecticut

Trail Name Difficulty Length (mi) Rating City
Cheshire Lock 12 Easiest difficulty 18.0 ***** Cheshire
East Rock Park Intermediate difficulty 5.0 ***** New Haven
Middlesex Community College Intermediate difficulty 20.0 ***** Middletown
Day Pond Intermediate difficulty 7.0 ***** Colchester
Nassahegan State Forest Intermediate difficulty 15.0 ***** Burlington
Millers Pond Advanced difficulty 5.0 ***** Durham
Grayville Falls Town Park Advanced difficulty 8.0 ***** Hebron
River Highlands State Park / Cromwell Creek Beginner difficulty 7.0 ***** Cromwell
Meshomasic State Forest Intermediate difficulty 30.0 ***** East Hampton
Wadsworth State Park Intermediate difficulty 5.0 **** Middletown
Rockland Preserve Intermediate difficulty 25.0 **** Madison
Nathan Hale Intermediate difficulty 21.0 **** Coventry
Case Mountain Intermediate difficulty 33.0 **** Manchester
West Hartford Reservoir Intermediate difficulty 10.0 **** West Hartford
Hurd State Park Intermediate difficulty 12.0 **** East Hampton
Old Saybrook Preserve Intermediate difficulty 20.0 **** Old Saybrook
Canfield difficulty 6.0 **** Deep RIver
Cockaponset State Forest Advanced difficulty 20.0 **** Chester
Gay City State Park Beginner difficulty 10.0 **** Hebron
Crescent Lake Intermediate difficulty 6 **** Southington
Heublein Tower Beginner difficulty 15.0 *** West Hartford
Winding Trails Beginner difficulty 5.0 *** Farmington
Hartman Park Intermediate difficulty 6.0 *** Salem
Tyler Mills Intermediate difficulty 10.0 *** Wallingford
Salmon River State Forest Intermediate difficulty 7.0 *** Colchester
West Rocks State Park Intermediate difficulty 12.0 *** New Haven
Supply Ponds Intermediate difficulty 10.0 *** Branford
Genesee Recreation Area Beginner difficulty 10.0 *** Madison
Powder Ridge Bike Park Intermediate difficulty 0 *** Middlefield
Sessions Woods difficulty 20.0 *** Burlington
Brotherin Trail System Intermediate difficulty 4.0 *** Madison
Stony Creek Quarry Preserve Intermediate difficulty 10.0 *** Branford
The Jumps Beginner difficulty 1.0 *** West Hartford
Devil's Hopyard Expert difficulty 12.0 *** East Haddam
Corn Fields Easiest difficulty 3.0 ** Madison
Brooksvale Park And Naugatuck State Forest Advanced difficulty 10.0 ** Hamden
Farmington Canal Heritage Trail Easiest difficulty 5.0 * Hamden
Outer Loop difficulty 1.0 Westbrook
Inner Loop difficulty 1.0 Westbrook
Van Otterloo Preserve difficulty 1.0 Bloomfield
Red Trail difficulty 1.0 East Hampton
Timberlands difficulty 5.0 Madison
Risley Resovior Loop difficulty 2.0 Vernon
Div Pond difficulty 2 Rocky Hill

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