20 Trails in New Haven, Connecticut

Rank Trail Name Difficulty Length (mi) Rating City
1. Rockland Preserve Intermediate difficulty 25.0 **** Madison
2. Westwoods Intermediate difficulty 30.0 **** Guilford
3. Wadsworth State Park Intermediate difficulty 5.0 **** Middletown
4. Larkin State Bridal Trail Easiest difficulty 10.0 **** Southbury
5. Tyler Mills Intermediate difficulty 10.0 *** Wallingford
6. West Rocks State Park Intermediate difficulty 12.0 *** New Haven
7. Twin Brooks Park Intermediate difficulty 8 ***** Trumbull
8. East Rock Park Intermediate difficulty 5.0 ***** New Haven
9. Rockhouse Hill Sanctuary Intermediate difficulty 12.0 ***** Oxford
10. Supply Ponds Intermediate difficulty 10.0 *** Branford
11. Yale Preserve Intermediate difficulty 6.0 ***** Woodbridge
12. Cheshire Lock 12 Easiest difficulty 18.0 ***** Cheshire
13. Middlebury Greenway Easiest difficulty 10.0 **** Middlebury
14. Powder Ridge Bike Park Intermediate difficulty 0 *** Middlefield
15. Stony Creek Quarry Preserve Intermediate difficulty 10.0 *** Branford
16. Racebrook Tract  difficulty 11.0 *** Middletown
17. Brooksvale Park And Naugatuck State Forest Advanced difficulty 10.0 ** Hamden
18. Farmington Canal Heritage Trail Easiest difficulty 5.0 * Hamden
19. Lower Paugussett State Forest  difficulty 6.0 Newtown
20. Timberlands  difficulty 5.0 Madison

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