20 Trails in Westport, Connecticut

Rank Trail Name Difficulty Length (mi) Rating City
1. Pequonnock River Valley State Park / Trumbull Intermediate difficulty 15.0 ***** Trumbull
2. Stillwell Woods Intermediate difficulty 4.0 **** Syosset
3. East Setauket Intermediate difficulty 11.0 ***** East Setauket
4. Meadowlark Park Intermediate difficulty 6.0 **** East Northport
5. Bennetts Pond Advanced difficulty 10.0 ***** Ridgefield
6. Trail View State Park Intermediate difficulty 10.0 **** Syosset
7. Trout Brook Valley Intermediate difficulty 20.0 **** Easton
8. Mianus River Park Intermediate difficulty 10.0 **** Stamford
9. Wilton Woods Intermediate difficulty 7.0 **** Wilton
10. Caumsett State Park Easiest difficulty 10.0 **** Lloyd Harbor
11. Farringtons Woods Intermediate difficulty 8.0 **** Danbury
12. Collis P Huntington State Park Intermediate difficulty 20.0 *** Bethel
13. Twin Brooks Park Intermediate difficulty 8 ***** Trumbull
14. Setauket/port Jefferson station greenway Easiest difficulty 4.0 ***** port Jefferson
15. Tarrywile Park Beginner difficulty 5.0 *** Danbury
16. Rockhouse Hill Sanctuary Intermediate difficulty 12.0 ***** Oxford
17. Cranberry Park Easiest difficulty 7.0 *** Norwalk`
18. Trumbull Rail Trail Easiest difficulty 6.0 ** Trumbull
19. Blue Trail (Trout Brook Valley)  difficulty 2.0 Westport
20. Monroe Rail Trail  difficulty 8.0 Monroe

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