43 Trails in Hopkinton, 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. Mt. Pisgah Intermediate difficulty 8.0 **** Northborough
4. F. Gilbert Hills State Park Intermediate difficulty 11.0 **** Foxboro
5. Rayburn Trails Intermediate difficulty 10.0 **** Millbury
6. Singletary Trails Intermediate difficulty 15.0 **** Millbury
7. Callahan State Park Beginner difficulty 10.0 **** Framingham
8. Plummer's Landing/ Goat Hill Advanced difficulty 15.0 **** Whitinsville
9. Douglas State Forest Intermediate difficulty 27.0 **** Douglas
10. Adams Farm Intermediate difficulty 10.0 **** Walpole
11. Wrentham State Forest Advanced difficulty 17.0 ***** Wrentham
12. Sutton State Forest Intermediate difficulty 12.0 **** Sutton
13. Weston College Land Beginner difficulty 5.0 **** Weston
14. Hale Reservation Beginner difficulty 10.0 **** Westwood
15. Hopkinton State Park Intermediate difficulty 10.0 **** Hopkinton
16. Franklin State Forest Intermediate difficulty 7.0 **** Franklin State Forest
17. West Hill Dam Intermediate difficulty 5.0 **** Upton
18. Ashland State Park Intermediate difficulty 7.0 *** Ashland
19. Prospect Hill Beginner difficulty 10.0 **** Waltham
20. Upton State Forest Beginner difficulty 12.0 *** Upton
21. Grafton Land Trust Intermediate difficulty 20.0 *** Grafton
22. Mendon Town Forest Intermediate difficulty 7.0 **** Mendon
23. Vaughn Hill/bower Spring Trail System(s) Advanced difficulty 4.0 **** Bolton/harvard
24. Henry S. Hunnewell Town Forest Intermediate difficulty 1.0 ***** Natick
25. Caryl Park Beginner difficulty 17.0 *** Dover
26. Nobscot Mtn. Intermediate difficulty 15.0 *** Sudbury
27. Rattlesnake Hill Advanced difficulty 7.0 ***** Bolton
28. Cold Harbor Brook Intermediate difficulty 5.0 *** Northborough
29. Noon Hill Reservation Beginner difficulty 8.0 *** Medfield
30. Beaver Pond Advanced difficulty 7.0 **** Franklin
31. Rocky Woods Beginner difficulty 7.0 ** Medfield
32. Lake Whitehall Advanced difficulty 7.0 *** Hopkinton
33. Green Hill Park Advanced difficulty 5.0 **** Worcester
34. Peppercorn Hill Intermediate difficulty 3.0 *** Upton
35. Middle School Loop Beginner difficulty 3.0 *** Nasonville
36. Yellow Beginner difficulty 5.0 *** Worcester
37. Boy Scout Trails Intermediate difficulty 2.0 *** Franklin
38. Gardner Hill Town Forest Intermediate difficulty 6.0 *** Stow
39. Jerico Town Forest Beginner difficulty 5.0 ** Weston
40. Weston Aquaduct and Unused Rail Loop difficulty 25.0 Weston
41. Colt Farm difficulty 5.0 North Smithfield
42. Black Hut Management Area difficulty 11.0 Glendale
43. Libby Trail difficulty 4.0 Westborough

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