46 Trails in Boston, Massachusetts
| Trail Name | Difficulty | Length (mi) | Rating | City |
|---|---|---|---|---|
| Adams Farm | Intermediate | 10.0 |    |
Walpole |
| Ames Nowell | Intermediate | 10.0 | |
Abington |
| Beals Cove Park | Beginner | 5.0 | |
Hingham |
| Beaver Brook North | Intermediate | 4.0 | |
Belmont |
| Belmont Conservation | Beginner | 10.0 | |
Belmont |
| Beverly Commons | Advanced | 10 | |
Beverly |
| Billerica State Forest | Intermediate | 9 | |
Billerica |
| Blue Hills | Intermediate | 5.0 | |
Milton |
| Borderland State Park | Intermediate | 7.0 | |
Sharon |
| Cannon Hills | Intermediate | 1 | |
Salem Ma |
| Carolina Hill | Intermediate | 10.0 | |
Marshfield |
| Caryl Park | Beginner | 17.0 | |
Dover |
| Charles River Loop | Easiest | 15 | |
Boston |
| Chebacco Woods | Intermediate | 10.0 | |
Hamilton |
| Chestnut Hill Reservoir Loop | 2 | |
Boston | |
| Cutler Park | Beginner | 6 | |
Newton Highlands |
| Duxbury | Intermediate | 8.0 | |
Duxbury |
| F. Gilbert Hills State Park | Intermediate | 11.0 | |
Foxboro |
| Great Brook State Park | Beginner | 15.0 | |
Carlise |
| Great Esker Park | Intermediate | 5.0 | |
Weymouth |
| Hale Reservation | Beginner | 10.0 | |
Westwood |
| Harold Parker State Forest | Advanced | 35 | |
Andover |
| Henry S. Hunnewell Town Forest | Intermediate | 1.0 | |
Natick |
| Horn Pond | Intermediate | 13 | |
Woburn |
| Jerico Town Forest | Beginner | 5.0 | |
Weston |
| Landlocked Forest | Intermediate | 7 | |
Burlington |
| Littles Brook | 2.0 | |
Burlington | |
| Lynn Woods Reservation | Intermediate | 0 | |
|
| Middlesex Fells Reservation | Intermediate | 8.0 | |
Winchester |
| Mill Pond Conservation Area | Intermediate | 10 | |
Burlington |
| Millenium Park | Easiest | 12.0 | |
West Roxbury |
| Needham Town Forest | Intermediate | 7.0 | |
Needham |
| Noon Hill Reservation | Beginner | 8.0 | |
Medfield |
| Prospect Hill | Beginner | 10.0 | |
Waltham |
| Reading Town Forest | 5.0 | |
Reading | |
| Rocky Woods | Beginner | 7.0 | |
Medfield |
| Russell Mill | Intermediate | 7.0 | |
Chelmsford |
| Swan Pond Road Trails | Easiest | 7 | |
Middleton |
| Western Greenway | Intermediate | 8.0 | |
Belmont |
| Weston Aquaduct and Unused Rail Loop | 25.0 | |
Weston | |
| Weston College Land | Beginner | 5.0 | |
Weston |
| Whipple Hill | Beginner | 4.0 | |
Lexington |
| Whitney And Thayer Woods/weir River Farm | Beginner | 10.0 | |
Cohasset |
| Wompatuck State Park | Intermediate | 15.0 | |
Hingham |
| World's End | Beginner | 5.0 | |
Hingham |
| Wrentham State Forest | Advanced | 17.0 | |
Wrentham |