Hikes near Winchester, Massachusetts
Ambleway maps 2,266 hikes within 60 miles of Winchester. The wildest is East Street & Greenwich Plains Road at 83% wild, 60 miles out in Quabbin Reservoir Reservation. Nothing within 5 miles of the centre scores as wild; the nearest that does is Bradford Pond Road, 11 miles out.
970 sunset spots near Winchester →
Hikes
A short drive · 5–25 miles
Lost 50 Trail
14 mi away · 2 mi · ▲ 27 ft
Sentinel Perimeter Acquisition Radar Excavation & Sentinel Powerplant Excavation via Lost 50 Trail
14 mi away · 2.8 mi · ▲ 27 ft
Crane Beach–Crane Estate Beach Loop, 5 beaches
25 mi away · 3.1 mi · ▲ 113 ft
Bradford Pond Road
11 mi away · 2 mi · ▲ 0 ft
Skyview Trail–Spalding Hill Road Trail, 4 sights
22 mi away · 1.9 mi · ▲ 173 ft
Beaver Pond Loop–Cottontail Lane, 5 sights
22 mi away · 3.5 mi · ▲ 197 ft
Blood Road
23 mi away · 2 mi · ▲ 138 ft
Long Trail–Skyview Trail Loop, 5 sights
22 mi away · 2.1 mi · ▲ 122 ft
Worth the drive · 25–60 miles
East Street & Greenwich Plains Road
60 mi away · 2 mi · ▲ 82 ft
Fisk Road & Greenwich Plains Road
60 mi away · 2.9 mi · ▲ 138 ft
Martin Road & Prospect Hill Road
58 mi away · 3.6 mi · ▲ 339 ft
Pierce Road
57 mi away · 2.2 mi · ▲ 167 ft
Gorge Trail–Soapstone Mtn Trail, 3 sights
56 mi away · 4.4 mi · ▲ 464 ft
Fay Martin Road & Prospect Hill Road
58 mi away · 4.3 mi · ▲ 198 ft
Canesto Brook Trail–Mill Pond Trail, 3 sights
46 mi away · 3.1 mi · ▲ 227 ft
Webster Springs Road
49 mi away · 3 mi · ▲ 55 ft
Show 8 less-wild hikesHide 8 less-wild hikes
North Reservoir–South Reservoir, 7 sights
2 mi away · 6.1 mi · ▲ 395 ft
Grinding Rock Hill–South Reservoir, 5 sights
2 mi away · 5 mi · ▲ 286 ft
rock sofa–North Reservoir Loop, 5 sights
2 mi away · 2.3 mi · ▲ 56 ft
Whipple Hill–Geology Viewpoint Loop, 5 lakes
2 mi away · 1 mi · ▲ 173 ft
Gerry Hill & South Reservoir via Brooks Road
2 mi away · 3.2 mi · ▲ 322 ft
Mill Pond Reservoir Loop via Bridge and Cliff
5 mi away · 1.9 mi · ▲ 31 ft
Mount Hood–Gas Pipeline Viewpoint, 7 lakes
5 mi away · 1.4 mi · ▲ 144 ft
South Reservoir–Bellevue Pond, 4 lakes
1 mi away · 3.1 mi · ▲ 328 ft