44 Trails in Middletown, 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. Case Mountain Intermediate difficulty 33.0 **** Manchester
6. River Highlands State Park / Cromwell Creek Beginner difficulty 7.0 ***** Cromwell
7. Middlesex Community College Intermediate difficulty 20.0 ***** Middletown
8. Cockaponset State Forest Advanced difficulty 20.0 **** Chester
9. Grayville Falls Town Park Advanced difficulty 8.0 ***** Hebron
10. Gay City State Park Beginner difficulty 10.0 **** Hebron
11. Wadsworth State Park Intermediate difficulty 5.0 **** Middletown
12. Meshomasic State Forest Intermediate difficulty 30.0 ***** East Hampton
13. Crescent Lake Intermediate difficulty 6 **** Southington
14. Nathan Hale Intermediate difficulty 21.0 **** Coventry
15. Tyler Mills Intermediate difficulty 10.0 *** Wallingford
16. Hurd State Park Intermediate difficulty 12.0 **** East Hampton
17. West Rocks State Park Intermediate difficulty 12.0 *** New Haven
18. Winding Trails Beginner difficulty 5.0 *** Farmington
19. East Rock Park Intermediate difficulty 5.0 ***** New Haven
20. Heublein Tower Beginner difficulty 15.0 *** West Hartford
21. Hartman Park Intermediate difficulty 6.0 *** Salem
22. Supply Ponds Intermediate difficulty 10.0 *** Branford
23. Old Saybrook Preserve Intermediate difficulty 20.0 **** Old Saybrook
24. Salmon River State Forest Intermediate difficulty 7.0 *** Colchester
25. Day Pond Intermediate difficulty 7.0 ***** Colchester
26. Cheshire Lock 12 Easiest difficulty 18.0 ***** Cheshire
27. Sessions Woods  difficulty 20.0 *** Burlington
28. Genesee Recreation Area Beginner difficulty 10.0 *** Madison
29. Devil's Hopyard Expert difficulty 12.0 *** East Haddam
30. The Jumps Beginner difficulty 1.0 *** West Hartford
31. Powder Ridge Bike Park Intermediate difficulty 0 *** Middlefield
32. Brotherin Trail System Intermediate difficulty 4.0 *** Madison
33. Stony Creek Quarry Preserve Intermediate difficulty 10.0 *** Branford
34. Canfield  difficulty 6.0 **** Deep RIver
35. Brooksvale Park And Naugatuck State Forest Advanced difficulty 10.0 ** Hamden
36. Farmington Canal Heritage Trail Easiest difficulty 5.0 * Hamden
37. Corn Fields Easiest difficulty 3.0 ** Madison
38. Red Trail  difficulty 1.0 East Hampton
39. Timberlands  difficulty 5.0 Madison
40. Outer Loop  difficulty 1.0 Westbrook
41. Van Otterloo Preserve  difficulty 1.0 Bloomfield
42. Risley Resovior Loop  difficulty 2.0 Vernon
43. Inner Loop  difficulty 1.0 Westbrook
44. Div Pond  difficulty 2 Rocky Hill

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