38 Trails in Winchester, Massachusetts
| Trail Name | Difficulty | Length (mi) | Rating | City |
|---|---|---|---|---|
| Henry S. Hunnewell Town Forest | Intermediate | 1.0 |  |
Natick |
| Ward Reservation | Intermediate | 12.0 | |
Andover |
| Billerica State Forest | Intermediate | 9 | |
Billerica |
| Harold Parker State Forest | Advanced | 35 |  |
Andover |
| Russell Mill | Intermediate | 7.0 |  |
Chelmsford |
| Lynn Woods Reservation | Intermediate | 0 | |
Saugus |
| Middlesex Fells Reservation | Intermediate | 8.0 | |
Winchester |
| Horn Pond | Intermediate | 13 | |
Woburn |
| Landlocked Forest | Intermediate | 7 | |
Burlington |
| Willowdale Forest | Beginner | 20.0 | |
Wenham |
| Cutler Park | Beginner | 6 | |
Newton Highlands |
| Beaver Brook North | Intermediate | 4.0 | |
Belmont |
| Western Greenway | Intermediate | 8.0 | |
Belmont |
| Merrimack River Trail | Beginner | 10.0 | |
Andover |
| Prospect Hill | Beginner | 10.0 | |
Waltham |
| Weston College Land | Beginner | 5.0 | |
Weston |
| Mill Pond Conservation Area | Intermediate | 10 | |
Burlington |
| Hale Reservation | Beginner | 10.0 | |
Westwood |
| Lowell-Dracut-Tyngsborough State Forest | Advanced | 10.0 | |
Lowell |
| Georgetown-rowley State Forest | Intermediate | 9.0 | |
Georgetown |
| Needham Town Forest | Intermediate | 7.0 | |
Needham |
| Belmont Conservation | Beginner | 10.0 | |
Belmont |
| Bradley Palmer | Beginner | 11.0 | |
Topsfield |
| Great Brook State Park | Beginner | 15.0 | |
Carlise |
| Bald Hill Reservation | Beginner | 10.0 | |
Boxford |
| Caryl Park | Beginner | 17.0 | |
Dover |
| Whipple Hill | Beginner | 4.0 | |
Lexington |
| Charles River Loop | Easiest | 15 | |
Boston |
| Beals Cove Park | Beginner | 5.0 | |
Hingham |
| Jerico Town Forest | Beginner | 5.0 | |
Weston |
| Great Esker Park | Intermediate | 5.0 | |
Weymouth |
| Swan Pond Road Trails | Easiest | 7 | |
Middleton |
| Millenium Park | Easiest | 12.0 | |
West Roxbury |
| Reading Town Forest | 5.0 | |
Reading | |
| Littles Brook | 2.0 | |
Burlington | |
| Weston Aquaduct and Unused Rail Loop | 25.0 | |
Weston | |
| Root Ball (Harold Parker State Forest) | 0.29 | |
Andover | |
| Chestnut Hill Reservoir Loop | 2 | |
Boston |