46 Trails in Boston, Massachusetts
| Rank | Trail Name | Difficulty | Length (mi) | Rating | City |
|---|---|---|---|---|---|
| 1. | Harold Parker State Forest | Advanced | 35 |   |
Andover |
| 2. | Lynn Woods Reservation | Intermediate | 0 |  |
Saugus |
| 3. | Russell Mill | Intermediate | 7.0 | |
Chelmsford |
| 4. | Middlesex Fells Reservation | Intermediate | 8.0 | |
Winchester |
| 5. | Landlocked Forest | Intermediate | 7 | |
Burlington |
| 6. | Wompatuck State Park | Intermediate | 15.0 | |
Hingham |
| 7. | Cutler Park | Beginner | 6 | |
Newton Highlands |
| 8. | F. Gilbert Hills State Park | Intermediate | 11.0 | |
Foxboro |
| 9. | Blue Hills | Intermediate | 5.0 | |
Milton |
| 10. | Billerica State Forest | Intermediate | 9 | |
Billerica |
| 11. | Duxbury | Intermediate | 8.0 | |
Duxbury |
| 12. | Borderland State Park | Intermediate | 7.0 | |
Sharon |
| 13. | Adams Farm | Intermediate | 10.0 | |
Walpole |
| 14. | Western Greenway | Intermediate | 8.0 | |
Belmont |
| 15. | Belmont Conservation | Beginner | 10.0 | |
Belmont |
| 16. | Needham Town Forest | Intermediate | 7.0 | |
Needham |
| 17. | Wrentham State Forest | Advanced | 17.0 | |
Wrentham |
| 18. | Mill Pond Conservation Area | Intermediate | 10 | |
Burlington |
| 19. | Horn Pond | Intermediate | 13 | |
Woburn |
| 20. | Great Brook State Park | Beginner | 15.0 | |
Carlise |
| 21. | Weston College Land | Beginner | 5.0 | |
Weston |
| 22. | Chebacco Woods | Intermediate | 10.0 | |
Hamilton |
| 23. | Hale Reservation | Beginner | 10.0 | |
Westwood |
| 24. | Carolina Hill | Intermediate | 10.0 | |
Marshfield |
| 25. | Prospect Hill | Beginner | 10.0 | |
Waltham |
| 26. | Beverly Commons | Advanced | 10 | |
Beverly |
| 27. | Ames Nowell | Intermediate | 10.0 | |
Abington |
| 28. | Beaver Brook North | Intermediate | 4.0 | |
Belmont |
| 29. | Charles River Loop | Easiest | 15 | |
Boston |
| 30. | Henry S. Hunnewell Town Forest | Intermediate | 1.0 | |
Natick |
| 31. | Caryl Park | Beginner | 17.0 | |
Dover |
| 32. | Whitney And Thayer Woods/weir River Farm | Beginner | 10.0 | |
Cohasset |
| 33. | Whipple Hill | Beginner | 4.0 | |
Lexington |
| 34. | Noon Hill Reservation | Beginner | 8.0 | |
Medfield |
| 35. | World's End | Beginner | 5.0 | |
Hingham |
| 36. | Rocky Woods | Beginner | 7.0 | |
Medfield |
| 37. | Great Esker Park | Intermediate | 5.0 | |
Weymouth |
| 38. | Beals Cove Park | Beginner | 5.0 | |
Hingham |
| 39. | Millenium Park | Easiest | 12.0 | |
West Roxbury |
| 40. | Jerico Town Forest | Beginner | 5.0 | |
Weston |
| 41. | Cannon Hills | Intermediate | 1 | |
Salem Ma |
| 42. | Weston Aquaduct and Unused Rail Loop | 25.0 | |
Weston | |
| 43. | Littles Brook | 2.0 | |
Burlington | |
| 44. | Reading Town Forest | 5.0 | |
Reading | |
| 45. | Swan Pond Road Trails | Easiest | 7 | |
Middleton |
| 46. | Chestnut Hill Reservoir Loop | 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.
