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Particularly Special Place
Top Rated Hiking Trails
near Ashfield, Massachusetts
Ashfield, Massachusetts 
Recommended Routes, Photos, & More
Difficult
Labyrinth and Lemon Squeeze
0.5 mi 0.9 km • 276' Up 84.2 m Up • 71' Down 21.51 m Down
New Paltz, NY
Difficult
Breakneck Ridge Trail
4.1 mi 6.6 km • 1,735' Up 528.89 m Up • 385' Down 117.5 m Down
Cornwal…, NY
Difficult
White Dot Trail
1.8 mi 3.0 km • 1,754' Up 534.76 m Up • 0' Down 0 m Down
Jaffrey, NH
Intermediate
Overlook Mountain Trail
2.3 mi 3.7 km • 1,376' Up 419.27 m Up • 0' Down 0 m Down
Woodstock, NY
Difficult
Gertrude's Nose Trail
2.9 mi 4.6 km • 329' Up 100.23 m Up • 489' Down 149.13 m Down
Kerhonkson, NY
Intermediate/Difficult
Pumpelly Trail
4.1 mi 6.6 km • 1,771' Up 539.67 m Up • 125' Down 38.09 m Down
Dublin, NH
Difficult
Bucklin Trail
3.7 mi 6.0 km • 2,392' Up 729.16 m Up • 47' Down 14.22 m Down
Rutland, VT
Intermediate/Difficult
Dublin Trail
2.4 mi 3.8 km • 1,690' Up 515.17 m Up • 20' Down 5.98 m Down
Dublin, NH
Intermediate/Difficult
AT: AMC - Berkshire Chapter (MA)
89.7 mi 144.4 km • 15,444' Up 4707.35 m Up • 14,639' Down 4461.95 m Down
Sheffield, MA
Intermediate
Ice Glen Trail
0.8 mi 1.2 km • 216' Up 65.98 m Up • 68' Down 20.59 m Down
Stockbr…, MA
Intermediate
Pisgah Ridge Trail
2.8 mi 4.6 km • 272' Up 82.86 m Up • 534' Down 162.76 m Down
Chester…, NH
Intermediate/Difficult
Millbrook Ridge Trail
2.9 mi 4.6 km • 737' Up 224.72 m Up • 169' Down 51.38 m Down
New Paltz, NY
Intermediate
Kaaterskill Falls Trail
1.1 mi 1.8 km • 666' Up 203 m Up • 118' Down 35.82 m Down
Palenville, NY
No Photos
Easy
Empire State Trail: Maybrook Trailway Section
25.5 mi 41.0 km • 444' Up 135.43 m Up • 615' Down 187.43 m Down
Brewster, NY
No Photos
Intermediate
Hoosac Range Trail
2.7 mi 4.3 km • 685' Up 208.78 m Up • 175' Down 53.29 m Down
North A…, MA
No Photos
Difficult
Lion's Head Trail
1.2 mi 2.0 km • 576' Up 175.49 m Up • 77' Down 23.38 m Down
Canaan, 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/Difficult
Perkins Trail
4.3 mi 6.8 km • 525' Up 159.95 m Up • 727' Down 221.7 m Down
Cold Sp…, NY
Difficult
Bonticou Ascent Path
0.4 mi 0.7 km • 63' Up 19.3 m Up • 177' Down 53.98 m Down
New Paltz, NY
Difficult
Pomperaug Trail - Blue
1.7 mi 2.7 km • 307' Up 93.56 m Up • 173' Down 52.76 m Down
Southbury, CT
No Photos
Difficult
Totem Trail
1.0 mi 1.6 km • 722' Up 220.02 m Up • 4' Down 1.17 m Down
Charlemont, MA
Intermediate
Yellow Trail
2.2 mi 3.6 km • 501' Up 152.56 m Up • 249' Down 75.94 m Down
Hamden, CT
Intermediate
Tower Trail
2.0 mi 3.2 km • 581' Up 177.16 m Up • 64' Down 19.63 m Down
East Co…, NH
Intermediate
Day Pond Brook Spur Trail
0.2 mi 0.4 km • 1' Up 0.19 m Up • 88' Down 26.89 m Down
East Ha…, CT
No Photos
Difficult
Sleeping Beauty Mountain Trail
2.7 mi 4.3 km • 979' Up 298.43 m Up • 258' Down 78.75 m Down
Whitehall, NY
No Photos
Intermediate
Hawley Bog Trail
0.3 mi 0.5 km • 1' Up 0.41 m Up • 27' Down 8.09 m Down
Charlemont, MA
Intermediate
Hemlock Brook Falls Spur
0.1 mi 0.1 km • 0' Up 0 m Up • 47' Down 14.37 m Down
William…, MA
