29 Trails in Chester, Connecticut

Trail Name Difficulty Length (mi) Rating City
Westwoods Intermediate difficulty 30.0 **** Guilford
Rockland Preserve Intermediate difficulty 25.0 **** Madison
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
Devil's Hopyard Expert difficulty 12.0 *** East Haddam
Hurd State Park Intermediate difficulty 12.0 **** East Hampton
Stony Creek Quarry Preserve Intermediate difficulty 10.0 *** Branford
Genesee Recreation Area Beginner difficulty 10.0 *** Madison
Mooween State Park Intermediate difficulty 8.0 ***** East Haddam
Grayville Falls Town Park Advanced difficulty 8.0 ***** Hebron
Day Pond Intermediate difficulty 7.0 ***** Colchester
Salmon River State Forest Intermediate difficulty 7.0 *** Colchester
River Highlands State Park / Cromwell Creek Beginner difficulty 7.0 ***** Cromwell
Canfield  difficulty 6.0 **** Deep RIver
Hartman Park Intermediate difficulty 6.0 *** Salem
Champlain Open Space Intermediate difficulty 5.0 **** Old Lyme
Wadsworth State Park Intermediate difficulty 5.0 **** Middletown
Hyper Coiler  difficulty 5.0 Old Lyme
Timberlands  difficulty 5.0 Madison
Millers Pond Advanced difficulty 5.0 ***** Durham
Rocky Neck State Park Intermediate difficulty 4.0 **** Niantic
Brotherin Trail System Intermediate difficulty 4.0 *** Madison
Corn Fields Easiest difficulty 3.0 ** Madison
Mile Creek Preserve Easiest difficulty 2.0 ***** Old Lyme
Outer Loop  difficulty 1.0 Westbrook
Inner Loop  difficulty 1.0 Westbrook
Red Trail  difficulty 1.0 East Hampton
Powder Ridge Bike Park Intermediate difficulty 0 *** Middlefield

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