RidgeSyncHiking Near Bennington, VT
Southwestern Vermont, where the Long Trail begins at the Massachusetts line and climbs into the Glastenbury Wilderness. 59 mapped hiking routes sit within 25 miles, each with a real elevation profile computed from the trail geometry.
59Trails within 25 mi
19Rated easy
960 ftAverage gain
1.1 miClosest trailhead
Waterfall Hikes (13)Lake & Pond Hikes (26)Summit Hikes (331)Hikes to Shelters (35)Loop Hikes (88)Easy Hikes (186)Hardest Hikes (60)Long Day Hikes (67)Short Hikes (213)Fire Tower Hikes (13)
Closest trailheads to Bennington
| Trail | From town | Distance | Gain | Difficulty |
|---|---|---|---|---|
| Ursa Way | 1.1 mi | 2.4 mi | 785 ft | Moderate |
| Bald Mountain Trail | 1.2 mi | 7.7 mi | 2,122 ft | Strenuous |
| Mount Anthony via Summit Trail | 1.4 mi | 2.3 mi | 1,238 ft | Moderate |
| Summit Trail and Zaphod's Run Loop | 1.4 mi | 1.7 mi | 692 ft | Easy |
| Zaphod's Run | 1.4 mi | 1.4 mi | 620 ft | Easy |
| Grime's Grind | 2 mi | 2.8 mi | 576 ft | Moderate |
| Mount Anthony via unmaintained | 2.7 mi | 3.5 mi | 555 ft | Moderate |
| Congdon Shelter via Appalachian Trail | 2.9 mi | 8.1 mi | 1,074 ft | Hard |
| Pond & Beaver dam via Appalachian Trail | 3.8 mi | 7.4 mi | 694 ft | Hard |
| Maple Hill via Appalachian Trail | 4.1 mi | 4 mi | 1,321 ft | Hard |
All 59 trails near Bennington
Ranked by popularity. Every figure is computed from the trail-snapped route geometry.
| Trail | Area | Distance | Gain | Difficulty |
|---|---|---|---|---|
| Lookout Rock via Summit Trail (Blue) | Manchester | 5.7 mi | 2,669 ft | Strenuous |
| Stratton Mountain via Appalachian Trail | Bromley & Stratton | 6.7 mi | 1,612 ft | Hard |
| Prospect Rock Loop via Appalachian Trail | Bromley & Stratton | 8.3 mi | 1,711 ft | Strenuous |
| Bald Mountain Trail | Bennington | 7.7 mi | 2,122 ft | Strenuous |
| Maple Hill via Appalachian Trail | Glastenbury | 4 mi | 1,321 ft | Hard |
| Mount Anthony via Summit Trail | Bennington | 2.3 mi | 1,238 ft | Moderate |
| Dome Trail | Bennington | 5 mi | 1,700 ft | Hard |
| Spruce Peak via Appalachian Trail | Bromley & Stratton | 7.9 mi | 1,381 ft | Hard |
| Glastenbury Mountain via Appalachian Trail | Glastenbury | 11.7 mi | 1,857 ft | Strenuous |
| Stratton Mountain via Stratton Pond Trail | Bromley & Stratton | 12.8 mi | 1,924 ft | Strenuous |
| Harmon Hill via Appalachian Trail | Glastenbury | 7.7 mi | 661 ft | Hard |
| Antone Mountain via Masters Mtn Trail | Manchester | 5.6 mi | 1,588 ft | Hard |
| The Gallop via Barton Trail | Manchester | 6.3 mi | 1,514 ft | Hard |
| Dome 2/3 Summit Trail | Bennington | 6.4 mi | 1,605 ft | Hard |
| Glastenbury Mountain via West Ridge Trail | Bennington | 17.5 mi | 3,149 ft | Strenuous |
| Haystack Mountain Trail | Glastenbury | 4 mi | 1,008 ft | Moderate |
| Bearclaw and Loop Trail | Brattleboro | 1.9 mi | 290 ft | Easy |
| Deer Knoll via Summit Trail (Blue) | Manchester | 6.1 mi | 461 ft | Moderate |
| Deer Knoll via Trout Lily Trail (White Purple) | Manchester | 2.4 mi | 558 ft | Moderate |
| Deer Knoll Loop via Mount Bluff Traili (White) | Manchester | 2.1 mi | 491 ft | Easy |
| Hagar Hill via Appalachian Trail | Glastenbury | 18.4 mi | 1,575 ft | Strenuous |
| Mount Anthony via unmaintained | Bennington | 3.5 mi | 555 ft | Moderate |
| Hogback Mountain via Raponda Ridge Trail | Brattleboro | 4.6 mi | 545 ft | Moderate |
| Hogback Mountain via Ware Road Connector | Brattleboro | 3.9 mi | 464 ft | Moderate |
| Hogback Mountain via Douglas Trail | Brattleboro | 2.4 mi | 340 ft | Easy |
| Hogback Mountain via White's Loop | Brattleboro | 2.2 mi | 211 ft | Easy |
| Lookout Rock via Beartown Road | Manchester | 6.5 mi | 1,947 ft | Strenuous |
| Prospect Rock via Appalachian Trail | Bromley & Stratton | 18.3 mi | 699 ft | Strenuous |
| Stratton Mountain via Stratton Ridge Trail | Bromley & Stratton | 1.2 mi | 102 ft | Easy |
| Stratton Pond via Catamount Trail | Bromley & Stratton | 7.4 mi | 495 ft | Moderate |
| Stratton Pond via Appalachian Trail | Bromley & Stratton | 6.8 mi | 357 ft | Moderate |
| Little Mud Pond via Appalachian Trail | Bromley & Stratton | 7.8 mi | 1,228 ft | Hard |
| Little Pond Mountain via Appalachian Trail | Glastenbury | 9.8 mi | 1,094 ft | Hard |
| Rice Hill via Loop Trail | Brattleboro | 1.8 mi | 258 ft | Easy |
| Prospect Rock via Branch Pond Trail | Bromley & Stratton | 14.7 mi | 222 ft | Moderate |
| Mount Olga via Tower Trail | Brattleboro | 1.1 mi | 253 ft | Easy |
| Mount Olga via Bishop Trail | Brattleboro | 1.5 mi | 462 ft | Easy |
| Lye Brook Falls via Lye Brook Trail | Bromley & Stratton | 4.5 mi | 857 ft | Moderate |
| Mount Olga Trail | Brattleboro | 1.4 mi | 525 ft | Easy |
| Deer Knoll via Mount Bluff Traili (White) | Manchester | 1.4 mi | 372 ft | Easy |
| Sucker Pond via Appalachian Trail | Glastenbury | 4.8 mi | 254 ft | Easy |
| Hagar Hill via Little Pond Road | Glastenbury | 2.2 mi | 173 ft | Easy |
| Masters Mtn Trail Loop | Manchester | 5.2 mi | 1,518 ft | Hard |
| Ursa Way | Bennington | 2.4 mi | 785 ft | Moderate |
| Pond & Beaver dam via Appalachian Trail | Glastenbury | 7.4 mi | 694 ft | Hard |
| West Ridge Trail | Bennington | 8.9 mi | 1,768 ft | Strenuous |
| Little Mud Pond via Stratton Pond Trail | Bromley & Stratton | 17.5 mi | 682 ft | Strenuous |
| Summit Trail and Zaphod's Run Loop | Bennington | 1.7 mi | 692 ft | Easy |
| Congdon Shelter Loop via Appalachian Trail | Glastenbury | 3.1 mi | 345 ft | Easy |
| Zaphod's Run | Bennington | 1.4 mi | 620 ft | Easy |
| Lake Raponda via Whites Road to West Lake Road | Brattleboro | 5.4 mi | 593 ft | Moderate |
| Grime's Grind | Bennington | 2.8 mi | 576 ft | Moderate |
| Congdon Shelter via Appalachian Trail | Glastenbury | 8.1 mi | 1,074 ft | Hard |
| Goddard Shelter via Appalachian Trail | Glastenbury | 19.4 mi | 2,088 ft | Strenuous |
| Bishop Trail and Rim Run Loop | Brattleboro | 1.9 mi | 469 ft | Easy |
| Kid Gore Shelter via Appalachian Trail | Glastenbury | 16.6 mi | 1,992 ft | Strenuous |
| Story Spring Shelter Loop via Appalachian Trail | Bromley & Stratton | 1.5 mi | 265 ft | Easy |
| Story Spring Shelter via Appalachian Trail | Bromley & Stratton | 1.5 mi | 216 ft | Easy |
| Mount Olga Trail (1.5 mi) | Brattleboro | 1.5 mi | 389 ft | Easy |
Frequently asked questions
Where can you hike near Bennington?
There are 59 mapped hiking routes within 25 miles of Bennington, 19 of them rated easy and 4 with 2,000 ft of climbing or more. The closest is Ursa Way, about 1.1 miles out.
What is the best hike near Bennington?
Lookout Rock via Summit Trail (Blue) is the most popular: 5.7 miles with 2,669 ft of gain, rated strenuous, about 20.5 miles from town.
Are there easy hikes near Bennington?
Yes — 19 of the 59 routes within 25 miles are rated easy, averaging well under an hour of climbing.