42 Trails in Lexington, 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. Cutler Park Beginner difficulty 6 **** Newton Highlands
7. Willowdale Forest Beginner difficulty 20.0 **** Wenham
8. Blue Hills Intermediate difficulty 5.0 **** Milton
9. Billerica State Forest Intermediate difficulty 9 ***** Billerica
10. Callahan State Park Beginner difficulty 10.0 **** Framingham
11. Lowell-Dracut-Tyngsborough State Forest Advanced difficulty 10.0 **** Lowell
12. Western Greenway Intermediate difficulty 8.0 **** Belmont
13. Belmont Conservation Beginner difficulty 10.0 *** Belmont
14. Needham Town Forest Intermediate difficulty 7.0 *** Needham
15. Mill Pond Conservation Area Intermediate difficulty 10 **** Burlington
16. Horn Pond Intermediate difficulty 13 **** Woburn
17. Great Brook State Park Beginner difficulty 15.0 *** Carlise
18. Weston College Land Beginner difficulty 5.0 **** Weston
19. Hale Reservation Beginner difficulty 10.0 **** Westwood
20. Georgetown-rowley State Forest Intermediate difficulty 9.0 **** Georgetown
21. Bald Hill Reservation Beginner difficulty 10.0 *** Boxford
22. Ward Reservation Intermediate difficulty 12.0 ***** Andover
23. Ashland State Park Intermediate difficulty 7.0 *** Ashland
24. Prospect Hill Beginner difficulty 10.0 **** Waltham
25. Beaver Brook North Intermediate difficulty 4.0 **** Belmont
26. Charles River Loop Easiest difficulty 15 ** Boston
27. Merrimack River Trail Beginner difficulty 10.0 **** Andover
28. Henry S. Hunnewell Town Forest Intermediate difficulty 1.0 ***** Natick
29. Caryl Park Beginner difficulty 17.0 *** Dover
30. Nobscot Mtn. Intermediate difficulty 15.0 *** Sudbury
31. Whipple Hill Beginner difficulty 4.0 *** Lexington
32. Rocky Woods Beginner difficulty 7.0 ** Medfield
33. Millenium Park Easiest difficulty 12.0 * West Roxbury
34. Jerico Town Forest Beginner difficulty 5.0 ** Weston
35. Hitchinpost Greens difficulty 1.0 *** Westford
36. Weston Aquaduct and Unused Rail Loop difficulty 25.0 Weston
37. Littles Brook difficulty 2.0 Burlington
38. Reading Town Forest difficulty 5.0 Reading
39. Swan Pond Road Trails Easiest difficulty 7 ** Middleton
40. Fort Rock difficulty 7.0 Littleton
41. Chestnut Hill Reservoir Loop difficulty 2 Boston
42. Root Ball (Harold Parker State Forest) difficulty 0.29 Andover

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