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Particularly Special Place
Top Rated Hiking Trails
near Oakham, Massachusetts
Oakham, Massachusetts 
Recommended Routes, Photos, & More
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/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
Saugatuck Trail
10.7 mi 17.3 km • 907' Up 276.43 m Up • 1,092' Down 332.76 m Down
Easton, CT
Easy
Needham Reservoir Trail
0.5 mi 0.8 km • 8' Up 2.4 m Up • 7' Down 2.23 m Down
Needham, MA
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
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
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
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
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
Norwalk River Valley Trail: Redding Mile
0.8 mi 1.3 km • 20' Up 5.98 m Up • 69' Down 20.98 m Down
Ridgefield, CT
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
