111 Trails in Connecticut

Rank Trail Name Difficulty Length (mi) Rating City
1. Pequonnock River Valley State Park / Trumbull Intermediate 15.0 ***** Trumbull
2. Rockland Preserve Intermediate 25.0 **** Madison
3. Cowles Park Intermediate 8.0 **** East Granby
4. Millers Pond Advanced 5.0 ***** Durham
5. Bluff Point State Park Intermediate 20.0 **** Groton
6. Nassahegan State Forest Intermediate 15.0 ***** Burlington
7. George C Waldo St Park Intermediate 7.0 ***** Southbury
8. Case Mountain Intermediate 33.0 **** Manchester
9. West Hartford Reservoir Intermediate 10.0 **** West Hartford
10. Bennetts Pond Advanced 10.0 ***** Ridgefield
11. Penwood State Park Advanced 7.0 ***** Bloomfield
12. River Highlands State Park / Cromwell Creek Beginner 7.0 ***** Cromwell
13. Trout Brook Valley Intermediate 20.0 **** Easton
14. Mianus River Park Intermediate 10.0 **** Stamford
15. Middlesex Community College Intermediate 20.0 ***** Middletown
16. Cockaponset State Forest Advanced 20.0 **** Chester
17. Grayville Falls Town Park Advanced 8.0 ***** Hebron
18. Gay City State Park Beginner 10.0 **** Hebron
19. Westwoods Intermediate 30.0 **** Guilford
20. Wilton Woods Intermediate 7.0 **** Wilton
21. Somers Mountain / Shenipsit SF Advanced 0.0 **** Somers
22. Wadsworth State Park Intermediate 5.0 **** Middletown
23. Thompson Dam Intermediate 10.0 **** Thompson
24. Meshomasic State Forest Intermediate 30.0 ***** East Hampton
25. Old Furnace Intermediate 8.0 **** Danielson
26. Crescent Lake Intermediate 6 **** Southington
27. Nathan Hale Intermediate 21.0 **** Coventry
28. Larkin State Bridal Trail Easiest 10.0 **** Southbury
29. Farringtons Woods Intermediate 8.0 **** Danbury
30. Tyler Mills Intermediate 10.0 *** Wallingford
31. Nepaug Intermediate 8.0 ***** New Hartford
32. Collis P Huntington State Park Intermediate 20.0 *** Bethel
33. Hurd State Park Intermediate 12.0 **** East Hampton
34. Sunny Valley Intermediate 7.0 **** Bridgewater
35. Dragon tail Intermediate 2.0 **** Groton
36. Mooween State Park Intermediate 8.0 ***** East Haddam
37. West Rocks State Park Intermediate 12.0 *** New Haven
38. Champlain Open Space Intermediate 5.0 **** Old Lyme
39. Twin Brooks Park Intermediate 8.0 ***** Trumbull
40. Tarrywile Park Beginner 5.0 *** Danbury
41. Carpenter's Falls Beginner 3.0 ***** Granby
42. Mansfield Hollow Beginner 18.0 **** Mansfield
43. Winding Trails Beginner 5.0 *** Farmington
44. East Rock Park Intermediate 5.0 ***** New Haven
45. Heublein Tower Beginner 15.0 *** West Hartford
46. Rocky Neck State Park Intermediate 4.0 **** Niantic
47. Hartman Park Intermediate 6.0 *** Salem
48. Supply Ponds Intermediate 10.0 *** Branford
49. Old Saybrook Preserve Intermediate 20.0 **** Old Saybrook
50. Salmon River State Forest Intermediate 7.0 *** Colchester