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Particularly Special Place
Family Friendly Hiking Routes
near Bolton, Massachusetts
Bolton, Massachusetts 
Recommended Routes, Photos, & More
Intermediate
Castle Craig
2.8 mi 4.5 km • 644' Up 196.41 m Up • 644' Down 196.37 m Down
Meriden, CT
Intermediate
Wright's Tower Out-and-Back
0.9 mi 1.5 km • 138' Up 42 m Up • 137' Down 41.88 m Down
Medford, MA
Intermediate
Vernal Pool Loop
1.8 mi 2.9 km • 99' Up 30.28 m Up • 99' Down 30.03 m Down
Sharon, MA
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
Pine Tree Trail
3.7 mi 6.0 km • 216' Up 65.94 m Up • 216' Down 65.98 m Down
Pocasset, 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
World's End Loop
3.1 mi 5.0 km • 181' Up 55.03 m Up • 180' Down 55.01 m Down
Hingham, MA
Easy/Intermediate
Ward Reservation
3.5 mi 5.7 km • 227' Up 69.24 m Up • 225' Down 68.67 m Down
Andover, MA
Easy/Intermediate
Virginia Woods Loop
0.9 mi 1.5 km • 117' Up 35.64 m Up • 118' Down 35.9 m Down
Melrose, MA
Intermediate
Franklin Park Loop
2.9 mi 4.7 km • 128' Up 38.98 m Up • 125' Down 38.05 m Down
Jamaica…, MA
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/Intermediate
Pine Mountain Loop
1.8 mi 2.9 km • 269' Up 82 m Up • 269' Down 81.88 m Down
New Durham, NH
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
Halibut Point Loop
1.1 mi 1.7 km • 50' Up 15.38 m Up • 50' Down 15.32 m Down
Rockport, MA
Intermediate
Little Ascutney Mountain
2.5 mi 4.0 km • 798' Up 243.33 m Up • 798' Down 243.34 m Down
Windsor, VT
Intermediate
Ipswich River Wildlife Sanctuary Loop
3.6 mi 5.7 km • 141' Up 42.86 m Up • 140' Down 42.58 m Down
Topsfield, MA
Easy
North River Loop
0.7 mi 1.2 km • 71' Up 21.78 m Up • 70' Down 21.44 m Down
Marshfi…, MA
Easy/Intermediate
Whipple Hill Loop
2.4 mi 3.8 km • 214' Up 65.25 m Up • 213' Down 65.06 m Down
Arlington, MA
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
Easy/Intermediate
Maudslay State Park Loop
3.7 mi 5.9 km • 146' Up 44.49 m Up • 145' Down 44.09 m Down
Amesbury, MA
Intermediate
Rocky Narrows Loop
4.6 mi 7.4 km • 345' Up 105.26 m Up • 343' Down 104.42 m Down
Sherborn, MA
Easy/Intermediate
Arnold Arboretum Tour
3.6 mi 5.7 km • 282' Up 85.97 m Up • 282' Down 85.95 m Down
Jamaica…, MA
