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Particularly Special Place
Family Friendly Hiking Trails
near Windham, New York
Windham, New York 
Recommended Routes, Photos, & More
Intermediate
Overlook Mountain Trail
2.3 mi 3.7 km • 1,376' Up 419.27 m Up • 0' Down 0 m Down
Woodstock, NY
Intermediate/Difficult
Saugatuck Trail
10.7 mi 17.3 km • 907' Up 276.43 m Up • 1,092' Down 332.76 m Down
Easton, CT
Easy
Shelton Lakes Recreation Path
4.4 mi 7.1 km • 263' Up 80.29 m Up • 223' Down 68.09 m Down
Shelton, CT
Intermediate
Cascade Trail
1.1 mi 1.7 km • 253' Up 77.17 m Up • 3' Down 0.82 m Down
North A…, MA
Intermediate
Kane Mountain North Trail
1.4 mi 2.3 km • 589' Up 179.61 m Up • 55' Down 16.81 m Down
Glovers…, NY
No Photos
Intermediate
9-Mile Truck Trail
9.0 mi 14.5 km • 530' Up 161.65 m Up • 518' Down 157.82 m Down
Norwich, NY
Easy/Intermediate
Tower Trail
1.6 mi 2.5 km • 512' Up 156.07 m Up • 3' Down 0.94 m Down
Hamden, CT
Easy
Nepaug Dam Trail
1.0 mi 1.6 km • 61' Up 18.51 m Up • 75' Down 22.84 m Down
Collins…, CT
No Photos
Intermediate
Green Trail
1.0 mi 1.6 km • 96' Up 29.28 m Up • 83' Down 25.44 m Down
Goldens…, NY
No Photos
Easy
Dutchess Rail Trail
15.0 mi 24.1 km • 446' Up 135.82 m Up • 471' Down 143.65 m Down
Hillsid…, NY
No Photos
Intermediate
Rensselaer Tech Park Trails, Bloomingdale Brook Falls Trail
1.0 mi 1.6 km • 141' Up 43.03 m Up • 139' Down 42.38 m Down
Menands, NY
No Photos
Easy
Harlem Valley Rail Trail: Ancram to Copake
5.3 mi 8.5 km • 125' Up 38.08 m Up • 149' Down 45.31 m Down
Boston…, NY
No Photos
Easy
Harlem Valley Rail Trail: Wassaic to Millerton
11.1 mi 17.9 km • 360' Up 109.62 m Up • 143' Down 43.46 m Down
Dover P…, NY
No Photos
Intermediate/Difficult
Stony Pond Loop
1.8 mi 2.9 km • 169' Up 51.5 m Up • 162' Down 49.3 m Down
Morrisv…, NY
Easy/Intermediate
Field Loop
1.0 mi 1.7 km • 143' Up 43.67 m Up • 144' Down 43.82 m Down
Lanesbo…, MA
No Photos
Intermediate
Perimeter Trail
1.6 mi 2.6 km • 190' Up 57.8 m Up • 192' Down 58.67 m Down
Redding, CT
Intermediate
Yellow Trail
1.2 mi 1.9 km • 362' Up 110.42 m Up • 18' Down 5.37 m Down
Weatogue, CT
Difficult
Red Trail
2.6 mi 4.2 km • 476' Up 145.12 m Up • 207' Down 63.06 m Down
Easton, CT
Intermediate
Pecoy Notch Trail
1.4 mi 2.3 km • 652' Up 198.6 m Up • 15' Down 4.63 m Down
Manorville, NY
Easy/Intermediate
Wallkill Valley Rail Trail
22.2 mi 35.8 km • 354' Up 108.04 m Up • 463' Down 141.16 m Down
Wallkill, NY
Easy
Dingmans Creek Trail
0.4 mi 0.6 km • 29' Up 8.9 m Up • 17' Down 5.11 m Down
Birchwo…, PA
Easy/Intermediate
Ashokan Rail Trail
12.0 mi 19.3 km • 252' Up 76.78 m Up • 191' Down 58.28 m Down
West Hu…, NY
Easy
Cedar Swamp Trail
1.6 mi 2.6 km • 34' Up 10.37 m Up • 76' Down 23.1 m Down
Matamoras, PA
Easy/Intermediate
Dennings Point Trail
0.7 mi 1.1 km • 45' Up 13.68 m Up • 56' Down 17.08 m Down
Beacon, NY
Difficult
Camp Smith Trail
3.5 mi 5.6 km • 1,076' Up 327.88 m Up • 565' Down 172.36 m Down
Peekskill, NY
Intermediate
Minisink Trail
3.5 mi 5.7 km • 318' Up 96.81 m Up • 539' Down 164.18 m Down
Matamoras, PA
Easy/Intermediate
Pond Loop Trail
0.7 mi 1.1 km • 14' Up 4.37 m Up • 64' Down 19.62 m Down
Georgetown, CT
No Photos
Intermediate
George W. Childs Park Trail
0.8 mi 1.3 km • 152' Up 46.28 m Up • 169' Down 51.48 m Down
Birchwo…, PA
