44 Trails in Middletown, Connecticut

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

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