38 Trails in Dover, 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. Middlesex Fells Reservation Intermediate difficulty 8.0 **** Winchester
4. Landlocked Forest Intermediate difficulty 7 **** Burlington
5. Cutler Park Beginner difficulty 6 **** Newton Highlands
6. F. Gilbert Hills State Park Intermediate difficulty 11.0 **** Foxboro
7. Blue Hills Intermediate difficulty 5.0 **** Milton
8. Borderland State Park Intermediate difficulty 7.0 **** Sharon
9. Callahan State Park Beginner difficulty 10.0 **** Framingham
10. Adams Farm Intermediate difficulty 10.0 **** Walpole
11. Western Greenway Intermediate difficulty 8.0 **** Belmont
12. Belmont Conservation Beginner difficulty 10.0 *** Belmont
13. Needham Town Forest Intermediate difficulty 7.0 *** Needham
14. Wrentham State Forest Advanced difficulty 17.0 ***** Wrentham
15. Horn Pond Intermediate difficulty 13 **** Woburn
16. Weston College Land Beginner difficulty 5.0 **** Weston
17. Hale Reservation Beginner difficulty 10.0 **** Westwood
18. Hopkinton State Park Intermediate difficulty 10.0 **** Hopkinton
19. Franklin State Forest Intermediate difficulty 7.0 **** Franklin State Forest
20. Ashland State Park Intermediate difficulty 7.0 *** Ashland
21. Prospect Hill Beginner difficulty 10.0 **** Waltham
22. Beaver Brook North Intermediate difficulty 4.0 **** Belmont
23. Charles River Loop Easiest difficulty 15 ** Boston
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. Whipple Hill Beginner difficulty 4.0 *** Lexington
28. Boxborough Area Trails Intermediate difficulty 10.0 *** Boxborough
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. Boy Scout Trails Intermediate difficulty 2.0 *** Franklin
33. Gardner Hill Town Forest Intermediate difficulty 6.0 *** Stow
34. Millenium Park Easiest difficulty 12.0 * West Roxbury
35. Jerico Town Forest Beginner difficulty 5.0 ** Weston
36. Weston Aquaduct and Unused Rail Loop difficulty 25.0 Weston
37. Littles Brook difficulty 2.0 Burlington
38. Chestnut Hill Reservoir Loop difficulty 2 Boston

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