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Particularly Special Place
Newest Recommended Hiking Routes
near Great Barrington, Massachusetts
Great Barrington, Massachusetts 
Recommended Routes, Photos, & More
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
Difficult
Ragged Mountain Blue and Red Blazed Loop
5.8 mi 9.4 km • 860' Up 262.17 m Up • 857' Down 261.32 m Down
Kensington, CT
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
Intermediate/Difficult
Manny's Swiss Army Knife Route
15.0 mi 24.1 km • 3,013' Up 918.36 m Up • 3,014' Down 918.66 m Down
Fort Mo…, NY
Intermediate
Illinois Mountain
5.6 mi 9.0 km • 1,004' Up 306.02 m Up • 527' Down 160.67 m Down
Highland, NY
Easy
Maples Farm Outer Loop
1.3 mi 2.1 km • 148' Up 45.19 m Up • 141' Down 42.94 m Down
Bozrah, CT
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
Intermediate/Difficult
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
Intermediate
Black Rock Loop
1.1 mi 1.8 km • 335' Up 102.24 m Up • 334' Down 101.83 m Down
Thomaston, 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
Northwoods Loop
10.6 mi 17.1 km • 1,499' Up 456.91 m Up • 1,498' Down 456.52 m Down
Durham, CT
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
Shenipsit Trail: Case Mountain to Gay City
6.6 mi 10.6 km • 1,024' Up 312.07 m Up • 860' Down 262.25 m Down
Manchester, CT
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/Difficult
Dunderberg, Bald Mountain, and Timp Loop
7.7 mi 12.4 km • 1,505' Up 458.87 m Up • 1,506' Down 459.12 m Down
Verplanck, NY
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
Schunnemunk Highlight - Otterkill to Megalith Loop
7.6 mi 12.2 km • 1,735' Up 528.98 m Up • 1,737' Down 529.5 m Down
Beaverd…, NY
Intermediate
Teatown Lake Cliffdale Farm Double Loop
6.2 mi 10.0 km • 519' Up 158.14 m Up • 504' Down 153.67 m Down
Croton-…, 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
Easy/Intermediate
Lake Wintergreen Loop
1.6 mi 2.6 km • 94' Up 28.63 m Up • 89' Down 27.02 m Down
Woodbridge, CT
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
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
Mill Street Loop
4.3 mi 6.9 km • 233' Up 70.98 m Up • 218' Down 66.46 m Down
Holden, MA
Intermediate
Barn Island Loop
3.9 mi 6.3 km • 174' Up 53.06 m Up • 175' Down 53.37 m Down
Pawcatuck, CT
Intermediate
Hook Mountain - Nyack Beach Loop - Rockland Lake, Congers, Upper Nyack
5.8 mi 9.4 km • 665' Up 202.83 m Up • 638' Down 194.42 m Down
Congers, NY
Intermediate
Pinnacle Mountain Loop
4.0 mi 6.5 km • 512' Up 155.94 m Up • 508' Down 154.89 m Down
Newfane, VT
