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Particularly Special Place
Top Rated Hiking Trails
near Bolton, Massachusetts
Bolton, Massachusetts 
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
Easy
Ocean View Loop Trail
1.5 mi 2.5 km • 40' Up 12.19 m Up • 36' Down 11.12 m Down
Newport, RI
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
Pisgah Ridge Trail
2.8 mi 4.6 km • 272' Up 82.86 m Up • 534' Down 162.76 m Down
Chester…, 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
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
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
Sammy C Trail
3.2 mi 5.2 km • 254' Up 77.47 m Up • 264' Down 80.39 m Down
Charles…, RI
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
Intermediate
Hawley Bog Trail
0.3 mi 0.5 km • 1' Up 0.41 m Up • 27' Down 8.09 m Down
Charlemont, MA
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
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
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
Intermediate/Difficult
Naugatuck (Blue) Trail
11.6 mi 18.6 km • 962' Up 293.28 m Up • 1,073' Down 327.03 m Down
Woodbridge, CT
No Photos
Intermediate
Morses Pond Trail
1.1 mi 1.8 km • 41' Up 12.41 m Up • 37' Down 11.36 m Down
Wellesley, MA
No Photos
Easy
Healthy Heart Trail
1.5 mi 2.5 km • 70' Up 21.4 m Up • 76' Down 23.13 m Down
Melrose, MA
Easy/Intermediate
Tower Trail
1.6 mi 2.5 km • 512' Up 156.07 m Up • 3' Down 0.94 m Down
Hamden, CT
Difficult
Mahican - Mohawk Trail Section 4: Charlemont - Cold River
10.9 mi 17.6 km • 1,846' Up 562.76 m Up • 1,237' Down 377.18 m Down
Charlemont, MA
Difficult
Bog Mountain Trail
2.8 mi 4.5 km • 953' Up 290.45 m Up • 683' Down 208.05 m Down
Wilmot, NH
No Photos
Intermediate
Hermit's Castle Trail
0.9 mi 1.4 km • 297' Up 90.46 m Up • 183' Down 55.84 m Down
Erving, MA
No Photos
Intermediate
Reservoir Road
6.9 mi 11.1 km • 987' Up 300.98 m Up • 404' Down 123.14 m Down
Hinsdale, NH
No Photos
Intermediate
Moraine Trail - Northern Section
2.7 mi 4.3 km • 208' Up 63.25 m Up • 244' Down 74.33 m Down
West Fa…, MA
