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Particularly Special Place
Newest Trail Running Routes
near Old Bennington, Vermont
Old Bennington, Vermont 
Recommended Routes, Photos, & More
Intermediate/Difficult
CT State Highpoint/Tri-point Out and Back
2.9 mi 4.7 km • 1,045' Up 318.64 m Up • 1,045' Down 318.48 m Down
Salisbury, CT
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
Sunset Rock
3.8 mi 6.1 km • 1,052' Up 320.51 m Up • 1,051' Down 320.32 m Down
Boston…, NY
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
Difficult
Monadnock White Cross/Dot Loop
4.0 mi 6.5 km • 1,775' Up 541.15 m Up • 1,779' Down 542.16 m Down
Jaffrey, NH
Intermediate
Little Ascutney Mountain
2.5 mi 4.0 km • 798' Up 243.33 m Up • 798' Down 243.34 m Down
Windsor, VT
Easy/Intermediate
All Trails Loop
7.4 mi 11.9 km • 718' Up 218.76 m Up • 728' Down 222.01 m Down
West Hu…, NY
Intermediate/Difficult
Northfield Mountain Trails
11.3 mi 18.3 km • 1,913' Up 583.11 m Up • 1,912' Down 582.9 m Down
Millers…, MA
Intermediate/Difficult
Bellows Pipe to Mt Greylock Summit
5.8 mi 9.4 km • 2,231' Up 679.9 m Up • 2,231' Down 679.86 m Down
Adams, MA
Difficult
Moreau 15k Loop
9.8 mi 15.7 km • 1,981' Up 603.77 m Up • 1,972' Down 601.14 m Down
Corinth, NY
Intermediate
New Boston Trail
2.1 mi 3.4 km • 599' Up 182.52 m Up • 598' Down 182.36 m Down
Pittsfield, VT
Intermediate
Leyden Blueberry Fields
7.5 mi 12.1 km • 1,167' Up 355.66 m Up • 1,188' Down 362.11 m Down
Bernard…, MA
Intermediate
Manchester to Monadnock 55 Miler
54.7 mi 88.0 km • 6,767' Up 2062.48 m Up • 5,530' Down 1685.58 m Down
Manchester, NH
Easy/Intermediate
Trout Brook Conservation Area Loop
3.8 mi 6.1 km • 195' Up 59.38 m Up • 195' Down 59.39 m Down
Holden, MA
Intermediate
Mill Street Loop
4.3 mi 6.9 km • 233' Up 70.98 m Up • 218' Down 66.46 m Down
Holden, MA
Intermediate
Pinnacle Mountain Loop
4.0 mi 6.5 km • 512' Up 155.94 m Up • 508' Down 154.89 m Down
Newfane, VT
Difficult
Sunapee Mountain Out-and-Back
5.1 mi 8.3 km • 1,576' Up 480.23 m Up • 1,575' Down 480.07 m Down
Newbury, NH
Intermediate
Pack Monadnock Loop
2.7 mi 4.4 km • 782' Up 238.33 m Up • 783' Down 238.66 m Down
Temple, NH
Difficult
Mohawk Trail Loop
5.1 mi 8.2 km • 1,133' Up 345.45 m Up • 1,119' Down 341.09 m Down
Charlemont, MA
Intermediate/Difficult
Savage Hill Wildlife Management Area
4.3 mi 7.0 km • 257' Up 78.27 m Up • 265' Down 80.77 m Down
Princeton, MA
Intermediate
Holbrook to Donker Farm
4.8 mi 7.8 km • 449' Up 136.85 m Up • 449' Down 136.79 m Down
Holden, MA
Intermediate/Difficult
Giant Ledge and Panther Mountain Out and Back
6.9 mi 11.1 km • 1,918' Up 584.68 m Up • 1,933' Down 589.16 m Down
Shokan, NY
Intermediate
Sanderson Brook Falls Trail
2.0 mi 3.2 km • 238' Up 72.54 m Up • 239' Down 72.79 m Down
Otis, MA
Intermediate
Mohonk 10-Mile Loop
9.8 mi 15.8 km • 774' Up 236.02 m Up • 730' Down 222.47 m Down
Stone R…, NY
Intermediate/Difficult
Mt. Tom Loop
5.1 mi 8.2 km • 907' Up 276.44 m Up • 907' Down 276.38 m Down
Woodstock, VT
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
Intermediate/Difficult
Rock the Ridge 50 Miler
51.8 mi 83.3 km • 4,653' Up 1418.13 m Up • 4,649' Down 1417.02 m Down
New Paltz, NY
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
