44 Trails in Middletown, Connecticut

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

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