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Particularly Special Place
Family Friendly Hiking Routes
near Southampton, Massachusetts
Southampton, Massachusetts 
Recommended Routes, Photos, & More
Intermediate/Difficult
Mount Greylock Summit Loop
6.6 mi 10.7 km • 2,251' Up 686.23 m Up • 2,246' Down 684.66 m Down
Adams, MA
Intermediate
Castle Craig
2.8 mi 4.5 km • 644' Up 196.41 m Up • 644' Down 196.37 m Down
Meriden, CT
Intermediate/Difficult
Bear Mountain
5.4 mi 8.7 km • 1,549' Up 472.12 m Up • 1,548' Down 471.96 m Down
Salisbury, CT
Intermediate/Difficult
Huckleberry Point
4.8 mi 7.7 km • 973' Up 296.52 m Up • 971' Down 296.07 m Down
Palenville, NY
Intermediate/Difficult
Mount Watatic and Nutting Hill Loop
2.8 mi 4.5 km • 644' Up 196.29 m Up • 645' Down 196.55 m Down
Ashburnham, MA
Intermediate
Wachusett Friendly Loop
3.6 mi 5.7 km • 832' Up 253.67 m Up • 825' Down 251.36 m Down
Princeton, MA
Intermediate/Difficult
North Pack Monadnock Mountain via Wapack Trail
3.1 mi 5.0 km • 921' Up 280.65 m Up • 921' Down 280.6 m Down
Greenfield, NH
Intermediate
West Thompson Lake
7.2 mi 11.6 km • 227' Up 69.34 m Up • 224' Down 68.35 m Down
Thompson, CT
Intermediate
Gap Mountain
2.6 mi 4.3 km • 602' Up 183.55 m Up • 602' Down 183.51 m Down
Troy, NH
Easy/Intermediate
Turkey Hill
1.6 mi 2.5 km • 307' Up 93.61 m Up • 308' Down 93.92 m Down
Fort Mo…, NY
Easy/Intermediate
Bedford Heritage Trail
1.8 mi 2.9 km • 47' Up 14.31 m Up • 47' Down 14.33 m Down
Bedford, NH
Easy
Rockwood Hall Short Loop
1.3 mi 2.2 km • 139' Up 42.4 m Up • 139' Down 42.33 m Down
Sleepy…, NY
Easy
Livingstong Park Loop
1.1 mi 1.8 km • 42' Up 12.79 m Up • 42' Down 12.92 m Down
Manchester, NH
Easy/Intermediate
Mohegan Park Loop
1.9 mi 3.1 km • 156' Up 47.56 m Up • 152' Down 46.19 m Down
Norwich, CT
Easy/Intermediate
Mt. Misery Loop
1.9 mi 3.1 km • 200' Up 60.89 m Up • 197' Down 59.92 m Down
Lincoln, MA
Intermediate/Difficult
Will Warren's Den and Lookout
2.5 mi 4.1 km • 421' Up 128.35 m Up • 422' Down 128.65 m Down
Farmington, CT
Intermediate
Rocky Narrows Loop
4.6 mi 7.4 km • 345' Up 105.26 m Up • 343' Down 104.42 m Down
Sherborn, MA
Intermediate
Mount Nimham Fire Tower
1.4 mi 2.3 km • 326' Up 99.5 m Up • 326' Down 99.47 m Down
Lake Ca…, NY
Intermediate
Godfrey Pond Loop
1.3 mi 2.1 km • 115' Up 34.91 m Up • 114' Down 34.86 m Down
Georgetown, CT
