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Particularly Special Place
Top Rated Hiking Trails
near Winchester, New Hampshire
Winchester, New Hampshire 
Recommended Routes, Photos, & More
Intermediate/Difficult
Mt. Major Trail
1.5 mi 2.4 km • 1,121' Up 341.64 m Up • 8' Down 2.56 m Down
Gilford, NH
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/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
Difficult
Caves Trail
0.1 mi 0.2 km • 90' Up 27.42 m Up • 10' Down 2.92 m Down
Holderness, NH
Intermediate/Difficult
Elwell Trail
9.3 mi 15.0 km • 1,370' Up 417.48 m Up • 2,785' Down 848.79 m Down
Alexandria, 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
No Photos
Difficult
Eagle Cliff Trail
2.5 mi 4.0 km • 1,569' Up 478.24 m Up • 174' Down 53.17 m Down
Sandwich, NH
Intermediate
Pisgah Ridge Trail
2.8 mi 4.6 km • 272' Up 82.86 m Up • 534' Down 162.76 m Down
Chester…, NH
No Photos
Easy/Intermediate
Five Finger Point Trail
2.0 mi 3.2 km • 131' Up 39.94 m Up • 277' Down 84.58 m Down
Holderness, NH
Easy
Needham Reservoir Trail
0.5 mi 0.8 km • 8' Up 2.4 m Up • 7' Down 2.23 m Down
Needham, MA
No Photos
Difficult
Brook Walk
0.8 mi 1.3 km • 170' Up 51.75 m Up • 228' Down 69.45 m Down
Moulton…, NH
Intermediate
Pine Hill Trail
0.4 mi 0.7 km • 499' Up 152.21 m Up • 0' Down 0 m Down
Princeton, MA
Intermediate
Cascade Trail
1.1 mi 1.7 km • 253' Up 77.17 m Up • 3' Down 0.82 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
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
No Photos
Intermediate
Mary's Mountain Trail
1.0 mi 1.7 km • 323' Up 98.4 m Up • 165' Down 50.42 m Down
Freedom, NH
Intermediate
Tower Trail
2.0 mi 3.2 km • 581' Up 177.16 m Up • 64' Down 19.63 m Down
East Co…, NH
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
Easy
Lake Trail
1.1 mi 1.8 km • 58' Up 17.53 m Up • 41' Down 12.44 m Down
Northwood, NH
Intermediate
Hemlock Brook Falls Spur
0.1 mi 0.1 km • 0' Up 0 m Up • 47' Down 14.37 m Down
William…, MA
No Photos
Easy/Intermediate
Ledges Loop Trail
0.7 mi 1.2 km • 106' Up 32.17 m Up • 134' Down 40.73 m Down
Northwood, NH
No Photos
Intermediate/Difficult
Weathersfield Trail
2.6 mi 4.2 km • 2,057' Up 626.95 m Up • 79' Down 24.16 m Down
Windsor, VT
Intermediate
Bald Knob Trail
0.7 mi 1.2 km • 76' Up 23.27 m Up • 40' Down 12.23 m Down
Moulton…, NH
No Photos
Intermediate
Pocumtuck Ridge Trail
3.9 mi 6.4 km • 1,092' Up 332.88 m Up • 1,073' Down 327.18 m Down
South D…, MA
