38 Trails in Winchester, 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. Billerica State Forest Intermediate difficulty 9 ***** Billerica
9. Lowell-Dracut-Tyngsborough State Forest Advanced difficulty 10.0 **** Lowell
10. Western Greenway Intermediate difficulty 8.0 **** Belmont
11. Belmont Conservation Beginner difficulty 10.0 *** Belmont
12. Needham Town Forest Intermediate difficulty 7.0 *** Needham
13. Mill Pond Conservation Area Intermediate difficulty 10 **** Burlington
14. Horn Pond Intermediate difficulty 13 **** Woburn
15. Great Brook State Park Beginner difficulty 15.0 *** Carlise
16. Weston College Land Beginner difficulty 5.0 **** Weston
17. Hale Reservation Beginner difficulty 10.0 **** Westwood
18. Georgetown-rowley State Forest Intermediate difficulty 9.0 **** Georgetown
19. Bald Hill Reservation Beginner difficulty 10.0 *** Boxford
20. Ward Reservation Intermediate difficulty 12.0 ***** Andover
21. Prospect Hill Beginner difficulty 10.0 **** Waltham
22. Bradley Palmer Beginner difficulty 11.0 *** Topsfield
23. Beaver Brook North Intermediate difficulty 4.0 **** Belmont
24. Charles River Loop Easiest difficulty 15 ** Boston
25. Merrimack River Trail Beginner difficulty 10.0 **** Andover
26. Henry S. Hunnewell Town Forest Intermediate difficulty 1.0 ***** Natick
27. Caryl Park Beginner difficulty 17.0 *** Dover
28. Whipple Hill Beginner difficulty 4.0 *** Lexington
29. Great Esker Park Intermediate difficulty 5.0 ** Weymouth
30. Beals Cove Park Beginner difficulty 5.0 ** Hingham
31. Millenium Park Easiest difficulty 12.0 * West Roxbury
32. Jerico Town Forest Beginner difficulty 5.0 ** Weston
33. Weston Aquaduct and Unused Rail Loop difficulty 25.0 Weston
34. Littles Brook difficulty 2.0 Burlington
35. Reading Town Forest difficulty 5.0 Reading
36. Swan Pond Road Trails Easiest difficulty 7 ** Middleton
37. Chestnut Hill Reservoir Loop difficulty 2 Boston
38. Root Ball (Harold Parker State Forest) difficulty 0.29 Andover

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