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Particularly Special Place
Top Trail Running Routes
near Chester Center, Connecticut
Chester Center, Connecticut 
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
Peanut Leap Cascade into Giant Stairs
4.2 mi 6.8 km • 744' Up 226.9 m Up • 746' Down 227.28 m Down
Northvale, NJ
Intermediate/Difficult
Rock Trail (RT) Loop
7.0 mi 11.3 km • 1,035' Up 315.48 m Up • 1,034' Down 315.22 m Down
Pound R…, NY
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
Intermediate
Castle Craig
2.8 mi 4.5 km • 644' Up 196.41 m Up • 644' Down 196.37 m Down
Meriden, CT
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
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
Cold Spring Harbor State Park Out-and-Back
4.2 mi 6.8 km • 571' Up 174.03 m Up • 570' Down 173.82 m Down
Cold Sp…, NY
Intermediate/Difficult
Robert Frost Trail
45.2 mi 72.7 km • 5,999' Up 1828.41 m Up • 6,848' Down 2087.21 m Down
Wendell, MA
Difficult
Macedonia Ridge Trail
6.4 mi 10.3 km • 1,592' Up 485.14 m Up • 1,586' Down 483.51 m Down
Kent, CT
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
Difficult
Soapstone Mountain Trail Race
13.8 mi 22.2 km • 1,815' Up 553.27 m Up • 1,836' Down 559.49 m Down
Staffor…, CT
Difficult
Long Path and Shore Trail Loop
5.8 mi 9.3 km • 575' Up 175.22 m Up • 550' Down 167.68 m Down
Alpine, NJ
No Photos
Intermediate
Leatherman's Loop
6.4 mi 10.3 km • 505' Up 153.9 m Up • 505' Down 153.96 m Down
Katonah, NY
Intermediate
White - Long Path - red - blue trail loop
4.8 mi 7.8 km • 900' Up 274.36 m Up • 900' Down 274.18 m Down
South N…, NY
Easy
East Beach Loop
2.3 mi 3.7 km • 16' Up 5 m Up • 18' Down 5.36 m Down
Charles…, RI
Intermediate/Difficult
Goat Peak Out-and-Back
0.9 mi 1.5 km • 277' Up 84.39 m Up • 277' Down 84.49 m Down
Eastham…, MA
Easy
Marine Park: West Loop
3.7 mi 5.9 km • 42' Up 12.67 m Up • 42' Down 12.65 m Down
Bensonh…, NY
Difficult
The Long Path
433.0 mi 696.8 km • 64,602' Up 19690.6 m Up • 57,200' Down 17434.5 m Down
Inwood, NY
Intermediate/Difficult
Nike Overlook Park
2.7 mi 4.3 km • 573' Up 174.62 m Up • 573' Down 174.63 m Down
Blauvelt, NY
Intermediate
Jerry Stage 6K
3.8 mi 6.0 km • 511' Up 155.77 m Up • 537' Down 163.61 m Down
Staffor…, CT
Intermediate
Blauvelt Northern Loop
4.0 mi 6.5 km • 468' Up 142.79 m Up • 463' Down 141.27 m Down
Blauvelt, NY
Difficult
Breakneck Ridge to South Beacon Mountain Firetower
9.2 mi 14.8 km • 3,181' Up 969.69 m Up • 3,179' Down 969.03 m Down
Cornwal…, NY
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
Easy/Intermediate
Yellow Loop/Nature Trail
3.7 mi 5.9 km • 226' Up 68.86 m Up • 233' Down 71.04 m Down
Riverside, CT
Intermediate/Difficult
Zoar Trail
6.4 mi 10.2 km • 1,105' Up 336.9 m Up • 1,105' Down 336.9 m Down
Oxford, CT
