32 Trails in Westwood, Massachusetts

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

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.