29 Trails in Chester, Connecticut

Rank Trail Name Difficulty Length (mi) Rating City
1. Rockland Preserve Intermediate difficulty 25.0 **** Madison
2. Millers Pond Advanced difficulty 5.0 ***** Durham
3. River Highlands State Park / Cromwell Creek Beginner difficulty 7.0 ***** Cromwell
4. Middlesex Community College Intermediate difficulty 20.0 ***** Middletown
5. Cockaponset State Forest Advanced difficulty 20.0 **** Chester
6. Grayville Falls Town Park Advanced difficulty 8.0 ***** Hebron
7. Westwoods Intermediate difficulty 30.0 **** Guilford
8. Wadsworth State Park Intermediate difficulty 5.0 **** Middletown
9. Hurd State Park Intermediate difficulty 12.0 **** East Hampton
10. Mooween State Park Intermediate difficulty 8.0 ***** East Haddam
11. Champlain Open Space Intermediate difficulty 5.0 **** Old Lyme
12. Rocky Neck State Park Intermediate difficulty 4.0 **** Niantic
13. Hartman Park Intermediate difficulty 6.0 *** Salem
14. Old Saybrook Preserve Intermediate difficulty 20.0 **** Old Saybrook
15. Salmon River State Forest Intermediate difficulty 7.0 *** Colchester
16. Day Pond Intermediate difficulty 7.0 ***** Colchester
17. Genesee Recreation Area Beginner difficulty 10.0 *** Madison
18. Devil's Hopyard Expert difficulty 12.0 *** East Haddam
19. Powder Ridge Bike Park Intermediate difficulty 0 *** Middlefield
20. Brotherin Trail System Intermediate difficulty 4.0 *** Madison
21. Stony Creek Quarry Preserve Intermediate difficulty 10.0 *** Branford
22. Canfield difficulty 6.0 **** Deep RIver
23. Mile Creek Preserve Easiest difficulty 2.0 ***** Old Lyme
24. Corn Fields Easiest difficulty 3.0 ** Madison
25. Red Trail difficulty 1.0 East Hampton
26. Hyper Coiler difficulty 5.0 Old Lyme
27. Timberlands difficulty 5.0 Madison
28. Outer Loop difficulty 1.0 Westbrook
29. Inner Loop difficulty 1.0 Westbrook

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