221 Trails in Massachusetts
| Rank | Trail Name | Difficulty | Length (mi) | Rating | City |
|---|---|---|---|---|---|
| 1. | Vietnam Trails | Intermediate | 20.0 |   |
Milford |
| 2. | Harold Parker State Forest | Advanced | 35 |  |
Andover |
| 3. | Lynn Woods Reservation | Intermediate | 0 | |
Saugus |
| 4. | Russell Mill | Intermediate | 7.0 | |
Chelmsford |
| 5. | Middlesex Fells Reservation | Intermediate | 8.0 | |
Winchester |
| 6. | Landlocked Forest | Intermediate | 7 | |
Burlington |
| 7. | Thunder Mountain Bike Park (Berkshire East) | Advanced | 5.0 | |
Charlemont |
| 8. | Wompatuck State Park | Intermediate | 15.0 | |
Hingham |
| 9. | Earl's Trails | Intermediate | 12.0 | |
Amherst |
| 10. | Village Park/ Abrams Rock | Intermediate | 5.0 | |
Swansea |
| 11. | Leominster State Forest | Advanced | 10.0 | |
Princeton |
| 12. | Cutler Park | Beginner | 6 | |
Newton Highlands |
| 13. | Otis | Intermediate | 30.0 | |
Bourne |
| 14. | West Barnstable Conservation Area | Intermediate | 12.0 | |
West Barnstable |
| 15. | F. Gilbert Hills State Park | Intermediate | 11.0 | |
Foxboro |
| 16. | Rayburn Trails | Intermediate | 10.0 | |
Millbury |
| 17. | Willowdale Forest | Beginner | 20.0 | |
Wenham |
| 18. | Blue Hills | Intermediate | 5.0 | |
Milton |
| 19. | Billerica State Forest | Intermediate | 9 | |
Billerica |
| 20. | Duxbury | Intermediate | 8.0 | |
Duxbury |
| 21. | Borderland State Park | Intermediate | 7.0 | |
Sharon |
| 22. | Singletary Trails | Intermediate | 15.0 | |
Millbury |
| 23. | Callahan State Park | Beginner | 10.0 | |
Framingham |
| 24. | Hodges Village Dam | Intermediate | 15.0 | |
Oxford |
| 25. | Pine Hills | Intermediate | 15.0 | |
Plymouth |
| 26. | Robinson state park | Intermediate | 25.0 | |
Agawam |
| 27. | Otis/atwood Conservation Area Loop (West Barnstable Conservation Area) | Intermediate | 2.0 | |
Hyannis |
| 28. | Lowell-Dracut-Tyngsborough State Forest | Advanced | 10.0 | |
Lowell |
| 29. | Plummer's Landing/ Goat Hill | Advanced | 15.0 | |
Whitinsville |
| 30. | Douglas State Forest | Intermediate | 27.0 | |
Douglas |
| 31. | Adams Farm | Intermediate | 10.0 | |
Walpole |
| 32. | Massasoit State Park | Intermediate | 0.0 | |
Taunton |
| 33. | Kenoza Lake | Intermediate | 10.0 | |
Haverhill |
| 34. | Wendell State Forest | Intermediate | 17.0 | |
Wendell |
| 35. | Western Greenway | Intermediate | 8.0 | |
Belmont |
| 36. | Amethyst Brook | Advanced | 7.0 | |
Amherst |
| 37. | Belmont Conservation | Beginner | 10.0 | |
Belmont |
| 38. | Sawmill Hills Conservation Area | Intermediate | 8.0 | |
Northampton |
| 39. | Needham Town Forest | Intermediate | 7.0 | |
Needham |
| 40. | Wrentham State Forest | Advanced | 17.0 | |
Wrentham |
| 41. | Wells State Park | Intermediate | 10.0 | |
Sturbridge |
| 42. | Mill Pond Conservation Area | Intermediate | 10 | |
Burlington |
| 43. | Horn Pond | Intermediate | 13 | |
Woburn |
| 44. | Sutton State Forest | Intermediate | 12.0 | |
Sutton |
| 45. | Mt. Pisgah | Intermediate | 8.0 | |
Northborough |
| 46. | Destruction Brook | Beginner | 15.0 | |
Dartmouth |
| 47. | Great Brook State Park | Beginner | 15.0 | |
Carlise |
| 48. | Weston College Land | Beginner | 5.0 | |
Weston |
| 49. | Wellfleet Ponds | Beginner | 20.0 | |
Wellfleet |
| 50. | Greenbriar Hodges Village Dam | Intermediate | 15.0 | |
Oxford |
