29 Trails in West Roxbury, Massachusetts

Rank Trail Name Difficulty Length (mi) Rating City
1. Lynn Woods Reservation Intermediate difficulty 0 **** Saugus
2. Middlesex Fells Reservation Intermediate difficulty 8.0 **** Winchester
3. Landlocked Forest Intermediate difficulty 7 **** Burlington
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. Adams Farm Intermediate difficulty 10.0 **** Walpole
9. Western Greenway Intermediate difficulty 8.0 **** Belmont
10. Belmont Conservation Beginner difficulty 10.0 *** Belmont
11. Needham Town Forest Intermediate difficulty 7.0 *** Needham
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. Prospect Hill Beginner difficulty 10.0 **** Waltham
16. Ames Nowell Intermediate difficulty 10.0 *** Abington
17. Beaver Brook North Intermediate difficulty 4.0 **** Belmont
18. Charles River Loop Easiest difficulty 15 ** Boston
19. Henry S. Hunnewell Town Forest Intermediate difficulty 1.0 ***** Natick
20. Caryl Park Beginner difficulty 17.0 *** Dover
21. Whipple Hill Beginner difficulty 4.0 *** Lexington
22. Noon Hill Reservation Beginner difficulty 8.0 *** Medfield
23. Rocky Woods Beginner difficulty 7.0 ** Medfield
24. Great Esker Park Intermediate difficulty 5.0 ** Weymouth
25. Millenium Park Easiest difficulty 12.0 * West Roxbury
26. Jerico Town Forest Beginner difficulty 5.0 ** Weston
27. Weston Aquaduct and Unused Rail Loop difficulty 25.0 Weston
28. Littles Brook difficulty 2.0 Burlington
29. Chestnut Hill Reservoir Loop difficulty 2 Boston

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