109 Trails in Connecticut

Rank Trail Name Difficulty Length (mi) Rating City
1. Pequonnock River Valley State Park / Trumbull Intermediate 15.0 ***** Trumbull
2. Millers Pond Advanced 5.0 ***** Durham
3. Nassahegan State Forest Intermediate 15.0 ***** Burlington
4. River Highlands State Park / Cromwell Creek Beginner 7.0 ***** Cromwell
5. Cowles Park Intermediate 8.0 **** East Granby
6. George C Waldo St Park Intermediate 7.0 ***** Southbury
7. Penwood State Park Advanced 7.0 ***** Bloomfield
8. Rockland Preserve Intermediate 25.0 **** Madison
9. Middlesex Community College Intermediate 20.0 ***** Middletown
10. Bluff Point State Park Intermediate 20.0 **** Groton
11. Somers Mountain / Shenipsit SF Advanced 0.0 **** Somers
12. Grayville Falls Town Park Advanced 8.0 ***** Hebron
13. Thompson Dam Intermediate 10.0 **** Thompson
14. Mooween State Park 8.0 East Haddam
15. East Rock Park 5.0 New Haven
16. Twin Brooks Park Intermediate 8.0 ***** Trumbull
17. Nepaug Intermediate 8.0 ***** New Hartford
18. Meshomasic State Forest Intermediate 30.0 ***** East Hampton
19. Wadsworth State Park Intermediate 5.0 **** Middletown
20. Champlain Open Space Intermediate 5.0 **** Old Lyme
21. Dragon tail Intermediate 2.0 **** Groton
22. Nathan Hale Intermediate 21.0 **** Coventry
23. Case Mountain Intermediate 33.0 **** Manchester
24. Trout Brook Valley Intermediate 20.0 **** Easton
25. West Hartford Reservoir Intermediate 10.0 **** West Hartford
26. Crescent Lake Intermediate 6.0 **** Southington
27. Westwoods Intermediate 30.0 **** Guilford
28. Farringtons Woods Intermediate 8.0 **** Danbury
29. Rockhouse Hill Sanctuary 12.0 Oxford
30. Cockaponset State Forest Advanced 20.0 **** Chester
31. Hurd State Park Intermediate 12.0 **** East Hampton
32. Gay City State Park Beginner 10.0 **** Hebron
33. Sunny Valley Intermediate 7.0 **** Bridgewater
34. Blue and Red trails Intermediate 5.0 **** Old Saybrook
35. Blue Trail (Trout Brook Valley) 2.0 Westport
36. Old Furnace Intermediate 8.0 **** Danielson
37. Old Saybrook Preserve Intermediate 20.0 **** Old Saybrook
38. Crandall Park Advanced 8.0 ***** Tolland
39. Mansfield Hollow Beginner 18.0 **** Mansfield
40. Steep Rock Advanced 7.0 **** Washington
41. Larkin State Bridal Trail Easiest 10.0 **** Southbury
42. Devil's Hopyard Expert 12.0 *** East Haddam
43. Upper Paugussett State Forest 6.0 Newtown
44. Middlebury Greenway Easiest 10.0 **** Middlebury
45. Monroe Rail Trail 8.0 Monroe
46. Canfield 6.0 **** Deep RIver
47. Day Pond Intermediate 7.0 ***** Colchester
48. Stratton Brook State Park Intermediate 5.0 **** Simsbury
49. Stony Creek Quarry Preserve 10.0 Branford
50. Cheshire Lock 12 Easiest 18.0 ***** Cheshire