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Particularly Special Place
Top Recommended Hiking Routes
near Osterville, Massachusetts
Osterville, Massachusetts 
Recommended Routes, Photos, & More
Intermediate/Difficult
Skyline Trail
7.5 mi 12.1 km • 846' Up 257.71 m Up • 863' Down 262.89 m Down
Winchester, MA
Difficult
Blue Hills Loop
4.1 mi 6.5 km • 1,171' Up 356.87 m Up • 1,165' Down 355.22 m Down
Dedham, MA
Easy
Sachuest Point Figure-Eight
2.7 mi 4.4 km • 58' Up 17.6 m Up • 57' Down 17.43 m Down
Newport, RI
Intermediate
Ponkapoag Pond Loop
4.4 mi 7.0 km • 229' Up 69.67 m Up • 228' Down 69.44 m Down
Milton, MA
Easy
Walden Pond
1.8 mi 2.9 km • 44' Up 13.43 m Up • 43' Down 13.18 m Down
Concord, MA
Intermediate/Difficult
Pamet Loop
5.4 mi 8.7 km • 239' Up 72.87 m Up • 239' Down 72.94 m Down
Truro, MA
Difficult
Long Pond (a.k.a. Moonrise Kingdom)
2.1 mi 3.3 km • 180' Up 54.94 m Up • 180' Down 54.96 m Down
Hope Va…, RI
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
Easy
East Beach Loop
2.3 mi 3.7 km • 16' Up 5 m Up • 18' Down 5.36 m Down
Charles…, RI
No Photos
Intermediate
Blackall Family and Ballou Farm Preserve
3.8 mi 6.2 km • 323' Up 98.6 m Up • 325' Down 98.97 m Down
Cumberl…, RI
Intermediate
Vernal Pool Loop
1.8 mi 2.9 km • 99' Up 30.28 m Up • 99' Down 30.03 m Down
Sharon, MA
Difficult
Wapack and Back
43.0 mi 69.1 km • 7,536' Up 2296.92 m Up • 7,536' Down 2296.83 m Down
Ashburnham, MA
Intermediate
Borderland State Park Loop
4.6 mi 7.4 km • 234' Up 71.21 m Up • 227' Down 69.31 m Down
Easton, MA
Intermediate
Lynn Woods Loop
7.0 mi 11.2 km • 543' Up 165.53 m Up • 541' Down 164.95 m Down
South P…, MA
Easy/Intermediate
Escoheag Trail Loop
6.5 mi 10.4 km • 556' Up 169.37 m Up • 558' Down 170.11 m Down
Hope Va…, RI
Intermediate
Hidden Lake Out-and-Back
4.0 mi 6.5 km • 135' Up 41.25 m Up • 137' Down 41.64 m Down
Hope Va…, RI
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
Table Rock - Canonchet Preserve
3.3 mi 5.4 km • 231' Up 70.47 m Up • 231' Down 70.49 m Down
Hopkinton, RI
Easy/Intermediate
Wellfleet Audobon Loop
1.7 mi 2.8 km • 57' Up 17.47 m Up • 58' Down 17.56 m Down
North E…, MA
Intermediate
Crane Beach Loop
3.9 mi 6.2 km • 119' Up 36.35 m Up • 119' Down 36.34 m Down
Ipswich, MA
Intermediate/Difficult
Rock Circuit Loop
4.6 mi 7.4 km • 619' Up 188.64 m Up • 619' Down 188.75 m Down
Medford, MA
Intermediate
Beaver Brook Loop
2.6 mi 4.2 km • 256' Up 78.08 m Up • 260' Down 79.11 m Down
Belmont, MA
Intermediate
Green Falls Narragansett Loop
3.0 mi 4.9 km • 186' Up 56.69 m Up • 185' Down 56.49 m Down
Preston…, CT
Intermediate
School House Pond
4.7 mi 7.5 km • 294' Up 89.7 m Up • 294' Down 89.74 m Down
Bradford, RI
Intermediate
Grills Preserve Loop
3.2 mi 5.2 km • 159' Up 48.56 m Up • 159' Down 48.39 m Down
Bradford, RI
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
Intermediate/Difficult
Buck Hill Loop
5.3 mi 8.6 km • 583' Up 177.75 m Up • 583' Down 177.79 m Down
Milton, MA
