Hikes near Westchester, Connecticut
Ambleway maps 1,732 hikes within 60 miles of Westchester. The wildest is Uncas Pond via Keeny Road at 84% wild, 12 miles out in Nehantic State Forest. The closest wild walking is Day Pond Road at 65% wild, 2 miles out.
427 sunset spots near Westchester →
Hikes
Within 5 miles
Cowgirl–Good Friday Loop, 4 sights
5 mi away · 3.6 mi · ▲ 373 ft

Day Pond Road
2 mi away · 4 mi · ▲ 483 ft
Dickinson Road Connector & River Road
2 mi away · 4 mi · ▲ 311 ft
Pines
2 mi away · 4.2 mi · ▲ 417 ft
Jones Street Pond via Grayville Road
5 mi away · 1.9 mi · ▲ 233 ft
Lyman Viaduct (buried)
2 mi away · 4.5 mi · ▲ 313 ft
Cowgirl–Good Friday, 4 sights
5 mi away · 3.3 mi · ▲ 318 ft
Salmon River Trail
2 mi away · 2 mi · ▲ 397 ft
A short drive · 5–25 miles
Uncas Pond via Keeny Road
12 mi away · 2.9 mi · ▲ 287 ft
Reservoir Road via Mulford Road
8 mi away · 4.1 mi · ▲ 566 ft
Brown Hill Loop via Keeny Road
12 mi away · 2.2 mi · ▲ 294 ft
Norwich Pond via Keeny Road
12 mi away · 2.8 mi · ▲ 257 ft
The Cascade & State Forest Quarry #1 Loop
7 mi away · 4.4 mi · ▲ 460 ft
Reservoir Road
7 mi away · 4.8 mi · ▲ 636 ft
Keeny Road
13 mi away · 2.9 mi · ▲ 272 ft
Meshomasic Mountain & Portland Reservoir Loop via Del Reeves Road
9 mi away · 4.6 mi · ▲ 575 ft
Worth the drive · 25–60 miles
East Street & Greenwich Plains Road
52 mi away · 2 mi · ▲ 82 ft
Fisk Road & Greenwich Plains Road
52 mi away · 2.9 mi · ▲ 138 ft
Axe Factory Road
29 mi away · 3.1 mi · ▲ 27 ft
Bruie Pond–Hampden Road, 3 sights
34 mi away · 4.6 mi · ▲ 505 ft
Pell Road
42 mi away · 3.6 mi · ▲ 219 ft
Crooked Ledge Road
51 mi away · 3.6 mi · ▲ 357 ft
Lookout–Springfield Water Works Intake Reservoir, 6 sights
47 mi away · 3.7 mi · ▲ 401 ft
Sweetman Mountain & North Lane Number One
45 mi away · 3.7 mi · ▲ 623 ft