34 Trails in Walpole, Massachusetts

Rank Trail Name Difficulty Length (mi) Rating City
1. Vietnam Trails Intermediate difficulty 20.0 **** Milford
2. Diamond Hill State Park Advanced difficulty 10.0 ***** Cumberland
3. Lincoln Woods Advanced difficulty 10.0 **** Lincoln
4. Cutler Park Beginner difficulty 6 **** Newton Highlands
5. F. Gilbert Hills State Park Intermediate difficulty 11.0 **** Foxboro
6. Blue Hills Intermediate difficulty 5.0 **** Milton
7. Borderland State Park Intermediate difficulty 7.0 **** Sharon
8. Callahan State Park Beginner difficulty 10.0 **** Framingham
9. Adams Farm Intermediate difficulty 10.0 **** Walpole
10. Western Greenway Intermediate difficulty 8.0 **** Belmont
11. Belmont Conservation Beginner difficulty 10.0 *** Belmont
12. Needham Town Forest Intermediate difficulty 7.0 *** Needham
13. Wrentham State Forest Advanced difficulty 17.0 ***** Wrentham
14. Weston College Land Beginner difficulty 5.0 **** Weston
15. Hale Reservation Beginner difficulty 10.0 **** Westwood
16. Hopkinton State Park Intermediate difficulty 10.0 **** Hopkinton
17. Franklin State Forest Intermediate difficulty 7.0 **** Franklin State Forest
18. Ashland State Park Intermediate difficulty 7.0 *** Ashland
19. Prospect Hill Beginner difficulty 10.0 **** Waltham
20. Ames Nowell Intermediate difficulty 10.0 *** Abington
21. Beaver Brook North Intermediate difficulty 4.0 **** Belmont
22. Charles River Loop Easiest difficulty 15 ** Boston
23. Henry S. Hunnewell Town Forest Intermediate difficulty 1.0 ***** Natick
24. Caryl Park Beginner difficulty 17.0 *** Dover
25. Nobscot Mtn. Intermediate difficulty 15.0 *** Sudbury
26. Noon Hill Reservation Beginner difficulty 8.0 *** Medfield
27. Beaver Pond Advanced difficulty 7.0 **** Franklin
28. Rocky Woods Beginner difficulty 7.0 ** Medfield
29. Mass Autobahn Beginner difficulty 5.0 ** Attleboro Ma
30. Boy Scout Trails Intermediate difficulty 2.0 *** Franklin
31. Millenium Park Easiest difficulty 12.0 * West Roxbury
32. Jerico Town Forest Beginner difficulty 5.0 ** Weston
33. Weston Aquaduct and Unused Rail Loop  difficulty 25.0 Weston
34. Chestnut Hill Reservoir Loop  difficulty 2 Boston

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