Hikes near Winchester Highlands, Massachusetts
Ambleway maps 2,235 hikes within 60 miles of Winchester Highlands. The wildest is Martin Road & Prospect Hill Road at 80% wild, 58 miles out. Nothing within 5 miles of the centre scores as wild; the nearest that does is Bradford Pond Road, 10 miles out.
960 sunset spots near Winchester Highlands →
Hikes
A short drive · 5–25 miles
Lost 50 Trail
13 mi away · 2 mi · ▲ 27 ft
Sentinel Perimeter Acquisition Radar Excavation & Sentinel Powerplant Excavation via Lost 50 Trail
13 mi away · 2.8 mi · ▲ 27 ft
Crane Beach–Crane Estate Beach Loop, 5 beaches
24 mi away · 3.1 mi · ▲ 113 ft
Bradford Pond Road
10 mi away · 2 mi · ▲ 0 ft
Skyview Trail–Spalding Hill Road Trail, 4 sights
21 mi away · 1.9 mi · ▲ 173 ft
Beaver Pond Loop–Cottontail Lane, 5 sights
21 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
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
57 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
47 mi away · 3.1 mi · ▲ 227 ft
Webster Springs Road
49 mi away · 3 mi · ▲ 55 ft
Copicut Hill–Copicut Road Loop, 4 sights
52 mi away · 2.9 mi · ▲ 170 ft
Cook Hill
59 mi away · 2.4 mi · ▲ 140 ft
Show 8 less-wild hikesHide 8 less-wild hikes
Ash Hill–Rocky Hill, 6 summits
4 mi away · 3.5 mi · ▲ 541 ft
Breakheart Hill–Pearce Lake, 5 lakes
4 mi away · 3.4 mi · ▲ 576 ft
Pearce Lake–Silver Lake, 5 sights
4 mi away · 3.7 mi · ▲ 587 ft
Ash Path
4 mi away · 2.5 mi · ▲ 358 ft
North Reservoir–South Reservoir, 7 sights
1 mi away · 6.1 mi · ▲ 395 ft
Grinding Rock Hill–South Reservoir, 5 sights
3 mi away · 5 mi · ▲ 286 ft
rock sofa–North Reservoir Loop, 5 sights
1 mi away · 2.3 mi · ▲ 56 ft
Silver Lake–Pipelline Trail, 3 sights
5 mi away · 1.9 mi · ▲ 252 ft