46 Trails in Boston, 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. F. Gilbert Hills State Park Intermediate difficulty 11.0 **** Foxboro
9. Blue Hills Intermediate difficulty 5.0 **** Milton
10. Billerica State Forest Intermediate difficulty 9 ***** Billerica
11. Duxbury Intermediate difficulty 8.0 **** Duxbury
12. Borderland State Park Intermediate difficulty 7.0 **** Sharon
13. Adams Farm Intermediate difficulty 10.0 **** Walpole
14. Western Greenway Intermediate difficulty 8.0 **** Belmont
15. Belmont Conservation Beginner difficulty 10.0 *** Belmont
16. Needham Town Forest Intermediate difficulty 7.0 *** Needham
17. Wrentham State Forest Advanced difficulty 17.0 ***** Wrentham
18. Mill Pond Conservation Area Intermediate difficulty 10 **** Burlington
19. Horn Pond Intermediate difficulty 13 **** Woburn
20. Great Brook State Park Beginner difficulty 15.0 *** Carlise
21. Weston College Land Beginner difficulty 5.0 **** Weston
22. Chebacco Woods Intermediate difficulty 10.0 ***** Hamilton
23. Hale Reservation Beginner difficulty 10.0 **** Westwood
24. Carolina Hill Intermediate difficulty 10.0 **** Marshfield
25. Prospect Hill Beginner difficulty 10.0 **** Waltham
26. Beverly Commons Advanced difficulty 10 **** Beverly
27. Ames Nowell Intermediate difficulty 10.0 *** Abington
28. Beaver Brook North Intermediate difficulty 4.0 **** Belmont
29. Charles River Loop Easiest difficulty 15 ** Boston
30. Henry S. Hunnewell Town Forest Intermediate difficulty 1.0 ***** Natick
31. Caryl Park Beginner difficulty 17.0 *** Dover
32. Whitney And Thayer Woods/weir River Farm Beginner difficulty 10.0 *** Cohasset
33. Whipple Hill Beginner difficulty 4.0 *** Lexington
34. Noon Hill Reservation Beginner difficulty 8.0 *** Medfield
35. World's End Beginner difficulty 5.0 *** Hingham
36. Rocky Woods Beginner difficulty 7.0 ** Medfield
37. Great Esker Park Intermediate difficulty 5.0 ** Weymouth
38. Beals Cove Park Beginner difficulty 5.0 ** Hingham
39. Millenium Park Easiest difficulty 12.0 * West Roxbury
40. Jerico Town Forest Beginner difficulty 5.0 ** Weston
41. Cannon Hills Intermediate difficulty 1 *** Salem Ma
42. Weston Aquaduct and Unused Rail Loop difficulty 25.0 Weston
43. Littles Brook difficulty 2.0 Burlington
44. Reading Town Forest difficulty 5.0 Reading
45. Swan Pond Road Trails Easiest difficulty 7 ** Middleton
46. Chestnut Hill Reservoir Loop difficulty 2 Boston

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