221 Trails in Massachusetts

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

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