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 ****
4. Russell Mill Intermediate 7.0 **** Chelmsford
5. Middlesex Fells Reservation Intermediate 8.0 **** Winchester
6. Landlocked Forest Intermediate 7 **** Burlington
7. Wompatuck State Park Intermediate 15.0 **** Hingham
8. Thunder Mountain Bike Park (Berkshire East) Advanced 5.0 ***** Charlemont
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. Amethyst Brook Advanced 7.0 **** Amherst
36. Western Greenway Intermediate 8.0 **** Belmont
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. Greenbriar Hodges Village Dam Intermediate 15.0 **** Oxford
50. Dogtown Advanced 15.0 ***** Gloucester