37 Trails in Cambridge, Massachusetts

Rank Trail Name Difficulty Length (mi) Rating City
1. Harold Parker State Forest Advanced difficulty 35 ***** Andover
2. Lynn Woods Reservation Intermediate difficulty 0 **** Saugus
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. Wompatuck State Park Intermediate difficulty 15.0 **** Hingham
7. Cutler Park Beginner difficulty 6 **** Newton Highlands
8. Blue Hills Intermediate difficulty 5.0 **** Milton
9. Billerica State Forest Intermediate difficulty 9 ***** Billerica
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. Prospect Hill Beginner difficulty 10.0 **** Waltham
20. Beaver Brook North Intermediate difficulty 4.0 **** Belmont
21. Charles River Loop Easiest difficulty 15 ** Boston
22. Henry S. Hunnewell Town Forest Intermediate difficulty 1.0 ***** Natick
23. Caryl Park Beginner difficulty 17.0 *** Dover
24. Whitney And Thayer Woods/weir River Farm Beginner difficulty 10.0 *** Cohasset
25. Whipple Hill Beginner difficulty 4.0 *** Lexington
26. Noon Hill Reservation Beginner difficulty 8.0 *** Medfield
27. World's End Beginner difficulty 5.0 *** Hingham
28. Rocky Woods Beginner difficulty 7.0 ** Medfield
29. Great Esker Park Intermediate difficulty 5.0 ** Weymouth
30. Beals Cove Park Beginner difficulty 5.0 ** Hingham
31. Millenium Park Easiest difficulty 12.0 * West Roxbury
32. Jerico Town Forest Beginner difficulty 5.0 ** Weston
33. Weston Aquaduct and Unused Rail Loop difficulty 25.0 Weston
34. Littles Brook difficulty 2.0 Burlington
35. Reading Town Forest difficulty 5.0 Reading
36. Swan Pond Road Trails Easiest difficulty 7 ** Middleton
37. Chestnut Hill Reservoir Loop difficulty 2 Boston

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