Top Recommended Hiking Routes
near Cheshire, Connecticut
Cheshire, Connecticut
Recommended Routes, Photos, & More
Breakneck Ridge Bypass
2.8 mi 4.5 km • 1,129' Up 344.21 m Up • 1,135' Down 346.08 m Down
Bear Mountain Loop
3.7 mi 5.9 km • 1,121' Up 341.56 m Up • 1,120' Down 341.52 m Down
Gertrude's Nose Loop
6.5 mi 10.5 km • 864' Up 263.34 m Up • 876' Down 267.14 m Down
The Devil's Path
23.1 mi 37.2 km • 8,104' Up 2470.13 m Up • 8,373' Down 2552.14 m Down
Storm King Mountain
2.4 mi 3.9 km • 455' Up 138.62 m Up • 460' Down 140.21 m Down
Breakneck Ridge to Sugarloaf Mountain Loop
6.1 mi 9.9 km • 1,490' Up 454.2 m Up • 1,483' Down 451.97 m Down
Peanut Leap Cascade into Giant Stairs
4.2 mi 6.8 km • 744' Up 226.9 m Up • 746' Down 227.28 m Down
Bonticou Crag Route
2.3 mi 3.7 km • 412' Up 125.51 m Up • 426' Down 129.71 m Down
Castle Craig
2.8 mi 4.5 km • 644' Up 196.41 m Up • 644' Down 196.37 m Down
Pyramid Mountain Loop
3.5 mi 5.6 km • 488' Up 148.63 m Up • 488' Down 148.84 m Down
Rock Trail (RT) Loop
7.0 mi 11.3 km • 1,035' Up 315.48 m Up • 1,034' Down 315.22 m Down
Minnewaska Lake Carriageway
1.6 mi 2.6 km • 176' Up 53.54 m Up • 199' Down 60.76 m Down
Cold Spring Harbor State Park Out-and-Back
4.2 mi 6.8 km • 571' Up 174.03 m Up • 570' Down 173.82 m Down
Popolopen Gorge - Timp-Torne Loop
4.3 mi 7.0 km • 1,157' Up 352.56 m Up • 1,092' Down 332.84 m Down
Bear Mountain
5.4 mi 8.7 km • 1,549' Up 472.12 m Up • 1,548' Down 471.96 m Down
Robert Frost Trail
40.2 mi 64.7 km • 5,360' Up 1633.58 m Up • 5,892' Down 1795.84 m Down
Macedonia Ridge Trail
6.4 mi 10.3 km • 1,592' Up 485.14 m Up • 1,586' Down 483.51 m Down
Anthony's Nose to Bear Mountain Bridge
6.0 mi 9.6 km • 1,446' Up 440.79 m Up • 1,446' Down 440.69 m Down
Lemon Squeeze, Bowling Rocks, and Valley of Boulders Loop
10.1 mi 16.3 km • 1,627' Up 495.81 m Up • 1,623' Down 494.83 m Down
Sky Top Tower via "The Trapps"
7.0 mi 11.2 km • 964' Up 293.86 m Up • 964' Down 293.68 m Down
Huckleberry Point
4.8 mi 7.7 km • 973' Up 296.52 m Up • 971' Down 296.07 m Down
Diamond Mountain
5.2 mi 8.4 km • 836' Up 254.71 m Up • 836' Down 254.75 m Down
North Point Loop
5.4 mi 8.6 km • 1,551' Up 472.66 m Up • 1,549' Down 472.1 m Down
Long Pond (a.k.a. Moonrise Kingdom)
2.1 mi 3.3 km • 180' Up 54.94 m Up • 180' Down 54.96 m Down
Norvin Green Highlights
7.1 mi 11.5 km • 1,430' Up 435.82 m Up • 1,429' Down 435.44 m Down
Catskills Black Dome and Blackhead Loop
6.2 mi 9.9 km • 2,245' Up 684.37 m Up • 2,247' Down 684.75 m Down
White - Long Path - red - blue trail loop
4.8 mi 7.8 km • 900' Up 274.36 m Up • 900' Down 274.18 m Down
Mohonk 10-Mile Loop
9.8 mi 15.8 km • 774' Up 236.02 m Up • 730' Down 222.47 m Down