Hiking in Windham County

Trails, best known first

• Long Trail 248 mi · end-to-end
• Appalachian Trail 143 mi · end-to-end
• Haystack Mountain Trail 2.0 mi · 1,010 ft climb · Moderate
• Mount Olga Trail 0.7 mi · 520 ft climb · Easy
• Mount Olga Trail 0.8 mi · 420 ft climb · Easy
• Stratton Pond Trail 3.6 mi · 470 ft climb · Moderate
• South Pond Loop 6.0 mi · 490 ft climb · end-to-end
• West River Trail 11 mi · 830 ft climb · Very strenuous · end-to-end
• Deerfield Ridge Trail 2.6 mi · 580 ft climb · Moderate
• Deerfield Ridge trail 1.1 mi · 200 ft climb · Easy
• Hoot Toot & Whistle Trail 1.9 mi · 40 ft climb · Easy
• West Cliff Trail 2.6 mi · 580 ft climb · Strenuous
• Hemlock Trail 3.3 mi · 840 ft climb · Strenuous
• Bemis Hill Trail 1.7 mi · 700 ft climb · Moderate
• Stratton Ridge Trail 0.7 mi · 110 ft climb · Easy
• Holden Trail 1.3 mi · 440 ft climb · Easy
• Jamie Latham Trail 2.0 mi · 380 ft climb · Moderate
• Rim Run 0.7 mi · 260 ft climb · Easy
• Cascade Trail 1.3 mi · 880 ft climb · Moderate
• Radford-Smith Trail 1.1 mi · 590 ft climb · Moderate
• Ridgeline Trail 3.0 mi · 600 ft climb · Strenuous
• Townline Trail 1.6 mi · 740 ft climb · Moderate
• Loop Trail 0.8 mi · 130 ft climb · Easy
• Ridgeline Trail 0.9 mi · 180 ft climb · Easy
• Cross Mountain Trail 0.3 mi · 70 ft climb · Easy
• Hathaway Trail 0.9 mi · 360 ft climb · Easy
• Overlook Trail 1.3 mi · 360 ft climb · Moderate
• Little Hogback Loop 0.6 mi · 110 ft climb · Easy
• Athens Access Path 0.8 mi · 550 ft climb · Easy
• Bishop Trail 0.5 mi · 280 ft climb · Easy
• Tower Trail (white) 0.3 mi · 100 ft climb · Easy
• Bear Claw 0.4 mi · 120 ft climb · Easy
• Spruced up 0.3 mi · 190 ft climb · Easy
• Tower Trail 0.1 mi · 30 ft climb · Easy
• Prospect Hill Trail 0.5 mi · 340 ft climb · Easy
• Hogback Summit Trail 0.4 mi · 90 ft climb · Easy
• Intermediate Woods Ascent 1.7 mi · 1,300 ft climb · Moderate
• Tower Trail 0.2 mi · 90 ft climb · Easy
• Catamount Trail 7.4 mi · 680 ft climb · Strenuous
• Deer Run Trail 1.8 mi · 950 ft climb · Moderate
• Private Trail 0.3 mi · 30 ft climb · Easy
• Windmill Hill Trail 1.2 mi · 810 ft climb · Moderate
• Tower Trail 0.1 mi · 60 ft climb · Easy
• Beginner Wanderer Summit Ascent 1.3 mi · 990 ft climb · Moderate
• Undercliff Trail 0.3 mi · 80 ft climb · Easy
• Beaver Pond Loop 1.5 mi · 130 ft climb · Easy
• Catamount Trail Section 4 5.0 mi · 110 ft climb · Moderate
• Dine Trail 1.5 mi · 170 ft climb · Easy
• Flood Dam Trail 2.3 mi · 310 ft climb · Moderate
• Forest Road 383 1.7 mi · 90 ft climb · Easy
• Hannum Trail 1.2 mi · 130 ft climb · Easy
• Pond Loop 2.4 mi · 150 ft climb · Easy
• West River Trail 3.6 mi · 60 ft climb · Easy
• Lye Brook Trail 9.1 mi · 2,260 ft climb · Very strenuous
• Intermediate Lower Mountain Loop 1.2 mi · 510 ft climb · Moderate
• Bare Hill Trail 1.2 mi · 360 ft climb · Moderate
• East Trail 1.7 mi · 70 ft climb · Easy
• Beginner Main Base to Sun Bowl 0.9 mi · 440 ft climb · Easy
• Branch Pond Trail 7.7 mi · 970 ft climb · Very strenuous
• Hamilton Falls Trail 1.0 mi · 580 ft climb · Easy
• Ledges overlook trail 1.4 mi · 660 ft climb · Moderate
• North Trail 1.3 mi · 880 ft climb · Moderate
• Ravine Trail 1.1 mi · 730 ft climb · Moderate
• Camp Trail 0.7 mi · 60 ft climb · Easy
• Advanced Summit Standard Ascent 0.7 mi · 1,020 ft climb · Moderate
• Beginner Lower Mountain Loop/ Intermediate Lower Mountain Loop/ Intermediate Summit Meadows Ascent 0.5 mi · 530 ft climb · Easy
• Dunn Nature Trail 1.0 mi · 150 ft climb · Easy
• Hinton Tail 0.7 mi · 40 ft climb · Easy
• Ice Pond 0.9 mi · 210 ft climb · Easy
• Morningside 0.8 mi · 240 ft climb · Easy
• Upper Woodlands 0.6 mi · 170 ft climb · Easy
• Crosstown Trail 1.0 mi · 120 ft climb · Easy
• East Trail 1.2 mi · 100 ft climb · Easy
• Forest Road 324 1.0 mi · 80 ft climb · Easy
• Ho Chi Minh Trail 1.5 mi · 410 ft climb · Moderate
• Little John Trail 1.7 mi · 190 ft climb · Easy
• North Brookwood Trail 1.4 mi · 190 ft climb · Easy
• Raponda Ridge Trail 1.2 mi · 210 ft climb · Easy
• Shearer Hill Trail 1.2 mi · 280 ft climb · Easy
• Valley Trail 1.6 mi · 280 ft climb · Easy
• Valley Trail 1.0 mi · 110 ft climb · Easy
• Valley Trail 2.1 mi · 370 ft climb · Moderate
• West Trail 2.1 mi · 220 ft climb · Moderate
• White's Loop 1.1 mi · 80 ft climb · Easy
• Beginner Wanderer Summit Ascent/ Intermediate Summit Meadows Ascent 0.9 mi · 620 ft climb · Easy
• IP Road 8.8 mi · 1,450 ft climb · Very strenuous
• Bobcat Run 0.6 mi · 130 ft climb · Easy
• Double Birch 0.6 mi · 30 ft climb · Easy
• Ed Dodd Trail 0.5 mi · 250 ft climb · Easy
• Headwaters Trail 0.7 mi · 150 ft climb · Easy
• Main Trail 0.8 mi · 140 ft climb · Easy
• Connector to Timber Ridge >>> 0.6 mi · 150 ft climb · Easy
• East Trail 0.5 mi · 60 ft climb · Easy
• High Road Trail 0.5 mi · 140 ft climb · Easy
• Lower Woodlands 0.5 mi · 160 ft climb · Easy
• Owl Ridge 0.4 mi · 60 ft climb · Easy
• Princess Pine 0.4 mi · 70 ft climb · Easy
• Valley Trail 0.3 mi · 10 ft climb · Easy
• Beginner Main Base to Sun Bowl/ Intermediate Lower Mountain Loop 0.6 mi · 270 ft climb · Easy
• Castle Brook Road 7.3 mi · 770 ft climb · Strenuous
• Intermediate Summit Meadows Ascent 0.5 mi · 450 ft climb · Easy
• Beginner Lower Mountain Loop 0.4 mi · 310 ft climb · Easy
• Bellows Falls Riverfront Trail 0.5 mi · 30 ft climb · Easy
• Douglas Trail 0.8 mi · 140 ft climb · Easy
• Hilltop Trail 0.8 mi · 120 ft climb · Easy
• Hoosac Tunnel and Wilmington Railroad 0.8 mi · 30 ft climb · Easy
• Logging Camp Trail 0.6 mi · 50 ft climb · Easy
• Rice Hill Trail 0.9 mi · 390 ft climb · Easy
• Ridge Trail 0.8 mi · 110 ft climb · Easy
• Sherwood Forest Trail 0.5 mi · 50 ft climb · Easy
• Three Bridges 0.6 mi · 100 ft climb · Easy
• V.A.S.T Trail 0.7 mi · 210 ft climb · Easy
• Valley Trail 0.6 mi · 120 ft climb · Easy
• Cliff Trail 0.4 mi · 60 ft climb · Easy
• Flood Dam Road 1.3 mi · 140 ft climb · Easy
• Forest Road 376 1.2 mi · 150 ft climb · Easy
• Gulf Road 1.1 mi · 150 ft climb · Easy
• Josh Road 1.2 mi · 260 ft climb · Easy
• Ober Hill Road 0.4 mi · 200 ft climb · Easy
• Roundabout 0.3 mi · 100 ft climb · Easy
• Sweet 0.3 mi · 180 ft climb · Easy
• Parsons Cutoff 0.6 mi · 390 ft climb · Easy
• Beginner Wanderer Summit Ascent/ Intermediate Woods Ascent 0.2 mi · 90 ft climb · Easy
• Play Nice 0.9 mi · 210 ft climb · Easy
• Corn Mill Crossing 0.3 mi · 20 ft climb · Easy
• Grout Pond - Somerset Reservoir 0.4 mi · 70 ft climb · Easy
• Just For Fun 0.3 mi · 30 ft climb · Easy
• Long Walk 0.1 mi · 0 ft climb · Easy
• North Overlook 0.3 mi · 170 ft climb · Easy
• Porcupine Ledge 0.4 mi · 330 ft climb · Easy
• School Trail 0.1 mi · 0 ft climb · Easy
• Shoulder Trail 0.4 mi · 160 ft climb · Easy
• Switchback 0.3 mi · 200 ft climb · Easy
• The Way In 0.2 mi · 30 ft climb · Easy
• Valley Trail 0.3 mi · 40 ft climb · Easy
• North Brookwood Trail 1.0 mi · 70 ft climb · Easy
• Beginner Lower Mountain Loop/ Intermediate Woods Ascent 0.2 mi · 110 ft climb · Easy
• Intermediate Lower Mountain Loop/ Intermediate Summit Meadows Ascent 453 ft · 60 ft climb · Easy
• Ashworth Road 0.9 mi · 260 ft climb · Easy
• Bear Hill Road 0.5 mi · 280 ft climb · Easy
• Smith Woods Road 0.9 mi · 90 ft climb · Easy
• Grade A 0.2 mi · 150 ft climb · Easy
• Middle Earth 0.1 mi · 0 ft climb · Easy
• Sugarhouse 0.2 mi · 30 ft climb · Easy
• Sylvan Park 0.2 mi · 10 ft climb · Easy
• Stratton Pond Spur 0.1 mi · 50 ft climb · Easy
• Angel Falls Extention Trail 0.2 mi · 130 ft climb · Easy
• Bemis Hill Road 0.2 mi · 130 ft climb · Easy
• Flame Trail 0.1 mi · 120 ft climb · Easy
• Labrynth Trail 0.1 mi · 10 ft climb · Easy
• Old Tavern Trail 0.2 mi · 50 ft climb · Easy
• Saxtons River Valley Trail 0.2 mi · 30 ft climb · Easy
• South Overlook 0.2 mi · 120 ft climb · Easy
• TRAIL ---NOT A THRU ROAD--- TRAIL 0.4 mi · 60 ft climb · Easy
• Valley Trail 0.2 mi · 0 ft climb · Easy
• The Connector 0.1 mi · 20 ft climb · Easy
• Sap Bucket 0.2 mi · 0 ft climb · Easy
• Spruce Loop 0.2 mi · 10 ft climb · Easy
• Connector 0.2 mi · 0 ft climb · Easy
• Tripping Field Access Trail 0.2 mi · 130 ft climb · Easy
• Halladay Brook Road 0.1 mi · 20 ft climb · Easy
• Melchen Road 0.2 mi · 80 ft climb · Easy
• <<< Connector from Timber Ridge 0.5 mi · 370 ft climb · Easy
• Connector from Magic Mountain >>> 0.8 mi · 340 ft climb · Easy
• <<< Connector to Magic Mountain 0.4 mi · 120 ft climb · Easy

Parking in Windham County

Lots with a gold seal are verified. The rest are not yet confirmed.

• Athens Access Path Trailhead 821 ft
• Beaver Pond Loop Trailhead 1,436 ft
• Catamount Trail Section 4 Trailhead 2,151 ft
• Catamount Trail Trailhead 2,151 ft
• Crosstown Trail Trailhead 2,023 ft
• Deer Run Nature Preserve 580 ft
• Dine Trailhead Parking 1,552 ft
• Dunn Nature Trail Trailhead 1,108 ft
• Ed Dodd Trail Trailhead 1,034 ft
• Forest Road 324 Trailhead 1,942 ft
• Hannum Trailhead Parking 1,480 ft
• Hinton Tail Trailhead 1,522 ft
• Hogback Mountain Parking 2,163 ft
• Holden Trail Trailhead 1,211 ft
• Hoot Toot & Whistle Trail Trailhead 1,492 ft
• Hoot Toot & Whistle Trail Trailhead (Wilmington) 1,522 ft
• Hoot Toot & Whistle Trail Trailhead (Wilmington) 1,508 ft
• Ice Pond Trailhead 348 ft
• Jamaica State Park Day Parking 687 ft
• Jamie Latham Trail Trailhead 1,463 ft
• Long Trail Trailhead (Stratton) 2,220 ft
• Long Walk Trailhead 526 ft
• Long Walk Trailhead (Saxtons River) 526 ft
• Long Walk Trailhead (Saxtons River) 533 ft
• Long Walk Trailhead (Saxtons River) 516 ft
• Morningside Trailhead 229 ft
• Pond Loop Trailhead (Stratton) 2,271 ft
• Rim Run Trailhead 2,175 ft
• School Trail Trailhead 398 ft
• SMC Parking Garage 2,129 ft
• South Pond 1,656 ft
• Stratton Pond Trail Trailhead 2,347 ft
• Sun Bowl Permit Parking 1,985 ft
• Upper Woodlands Trailhead 468 ft
• Valley Trail Trailhead 1,711 ft
• West River Trail Trailhead 1,028 ft
• West River Trail Trailhead (Brattleboro) 271 ft
• West River Trail Trailhead (Brattleboro) 233 ft
• West River Trail Trailhead (Brattleboro) 231 ft
• West River Trail Trailhead (Jamaica) 958 ft
• West River Trail Trailhead (Jamaica) 949 ft
• West River Trail Trailhead (Londonderry) 1,049 ft
• West River Trail Trailhead (Londonderry) 1,048 ft
• Windmill Hill Trail Trailhead 576 ft