27 Trails in Cheshire, 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. Nassahegan State Forest Intermediate difficulty 15.0 ***** Burlington
4. West Hartford Reservoir Intermediate difficulty 10.0 **** West Hartford
5. Westwoods Intermediate difficulty 30.0 **** Guilford
6. Wadsworth State Park Intermediate difficulty 5.0 **** Middletown
7. Crescent Lake Intermediate difficulty 6 **** Southington
8. Larkin State Bridal Trail Easiest difficulty 10.0 **** Southbury
9. Tyler Mills Intermediate difficulty 10.0 *** Wallingford
10. West Rocks State Park Intermediate difficulty 12.0 *** New Haven
11. Winding Trails Beginner difficulty 5.0 *** Farmington
12. East Rock Park Intermediate difficulty 5.0 ***** New Haven
13. Rockhouse Hill Sanctuary Intermediate difficulty 12.0 ***** Oxford
14. Supply Ponds Intermediate difficulty 10.0 *** Branford
15. Yale Preserve Intermediate difficulty 6.0 ***** Woodbridge
16. Cheshire Lock 12 Easiest difficulty 18.0 ***** Cheshire
17. Sessions Woods difficulty 20.0 *** Burlington
18. Middlebury Greenway Easiest difficulty 10.0 **** Middlebury
19. Genesee Recreation Area Beginner difficulty 10.0 *** Madison
20. Powder Ridge Bike Park Intermediate difficulty 0 *** Middlefield
21. Stony Creek Quarry Preserve Intermediate difficulty 10.0 *** Branford
22. Racebrook Tract difficulty 11.0 *** Middletown
23. Brooksvale Park And Naugatuck State Forest Advanced difficulty 10.0 ** Hamden
24. Thomaston Dam Easiest difficulty 0.0 *** Thomaston
25. Farmington Canal Heritage Trail Easiest difficulty 5.0 * Hamden
26. Rockwell Park difficulty 0 Bristol
27. Timberlands difficulty 5.0 Madison

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