26 Trails in Southbury, Connecticut

Rank Trail Name Difficulty Length (mi) Rating City
1. Pequonnock River Valley State Park / Trumbull Intermediate difficulty 15.0 ***** Trumbull
2. George C Waldo St Park Intermediate difficulty 7.0 ***** Southbury
3. Bennetts Pond Advanced difficulty 10.0 ***** Ridgefield
4. Trout Brook Valley Intermediate difficulty 20.0 **** Easton
5. Wilton Woods Intermediate difficulty 7.0 **** Wilton
6. Larkin State Bridal Trail Easiest difficulty 10.0 **** Southbury
7. Collis P Huntington State Park Intermediate difficulty 20.0 *** Bethel
8. Sunny Valley Intermediate difficulty 7.0 **** Bridgewater
9. West Rocks State Park Intermediate difficulty 12.0 *** New Haven
10. Twin Brooks Park Intermediate difficulty 8 ***** Trumbull
11. Tarrywile Park Beginner difficulty 5.0 *** Danbury
12. Rockhouse Hill Sanctuary Intermediate difficulty 12.0 ***** Oxford
13. Yale Preserve Intermediate difficulty 6.0 ***** Woodbridge
14. Steep Rock Advanced difficulty 7.0 **** Washington
15. Middlebury Greenway Easiest difficulty 10.0 **** Middlebury
16. Dingle Brook Trail  difficulty 6.0 *** Newtown
17. Racebrook Tract  difficulty 11.0 *** Middletown
18. Thomaston Dam Easiest difficulty 0.0 *** Thomaston
19. Gurski Farm Intermediate difficulty 4.0 *** Brookfield
20. Trumbull Rail Trail Easiest difficulty 6.0 ** Trumbull
21. Upper Paugussett State Forest  difficulty 6.0 Newtown
22. Funny Farm North Beginner difficulty 5.0 * Newtown
23. Lower Paugussett State Forest  difficulty 6.0 Newtown
24. Rockwell Park  difficulty 0 Bristol
25. Blue Trail (Trout Brook Valley)  difficulty 2.0 Westport
26. Monroe Rail Trail  difficulty 8.0 Monroe

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