41 Trails in Weston, Massachusetts

Rank Trail Name Difficulty Length (mi) Rating City
1. Vietnam Trails Intermediate difficulty 20.0 **** Milford
2. Harold Parker State Forest Advanced difficulty 35 ***** Andover
3. Russell Mill Intermediate difficulty 7.0 **** Chelmsford
4. Middlesex Fells Reservation Intermediate difficulty 8.0 **** Winchester
5. Landlocked Forest Intermediate difficulty 7 **** Burlington
6. Cutler Park Beginner difficulty 6 **** Newton Highlands
7. Blue Hills Intermediate difficulty 5.0 **** Milton
8. Billerica State Forest Intermediate difficulty 9 ***** Billerica
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. Mill Pond Conservation Area Intermediate difficulty 10 **** Burlington
15. Horn Pond Intermediate difficulty 13 **** Woburn
16. Great Brook State Park Beginner difficulty 15.0 *** Carlise
17. Weston College Land Beginner difficulty 5.0 **** Weston
18. Hale Reservation Beginner difficulty 10.0 **** Westwood
19. Hopkinton State Park Intermediate difficulty 10.0 **** Hopkinton
20. Ashland State Park Intermediate difficulty 7.0 *** Ashland
21. Prospect Hill Beginner difficulty 10.0 **** Waltham
22. Oak Hill Advanced difficulty 8.0 **** Littleton
23. Beaver Brook North Intermediate difficulty 4.0 **** Belmont
24. Charles River Loop Easiest difficulty 15 ** Boston
25. Henry S. Hunnewell Town Forest Intermediate difficulty 1.0 ***** Natick
26. Caryl Park Beginner difficulty 17.0 *** Dover
27. Nobscot Mtn. Intermediate difficulty 15.0 *** Sudbury
28. Whipple Hill Beginner difficulty 4.0 *** Lexington
29. Boxborough Area Trails Intermediate difficulty 10.0 *** Boxborough
30. Noon Hill Reservation Beginner difficulty 8.0 *** Medfield
31. Rocky Woods Beginner difficulty 7.0 ** Medfield
32. Gardner Hill Town Forest Intermediate difficulty 6.0 *** Stow
33. Millenium Park Easiest difficulty 12.0 * West Roxbury
34. Jerico Town Forest Beginner difficulty 5.0 ** Weston
35. Hitchinpost Greens  difficulty 1.0 *** Westford
36. Weston Aquaduct and Unused Rail Loop  difficulty 25.0 Weston
37. Littles Brook  difficulty 2.0 Burlington
38. Reading Town Forest  difficulty 5.0 Reading
39. Fort Rock  difficulty 7.0 Littleton
40. Chestnut Hill Reservoir Loop  difficulty 2 Boston
41. Special Ops (♦)  difficulty 0.68 Groton

Know of a new mountain bike trail not listed here? Please tell us about it using this form. Find mountain bike trails near you or for even more trail inspiration and how we ranked the mountain bike trails, see this list of the best mountain bike trails in the world.