4.6
(5508)
17,951
hikers
03:25
8.10km
710m
Hiking
Hike the challenging Windsor Trail up Mount Ascutney, featuring Gerry's Falls and panoramic views from the summit observation tower.
Last updated: February 26, 2026
Waypoints
Start point
Parking
Get Directions
1.17 km
Highlight • Waterfall
Tip by
3.98 km
Highlight • Monument
Tip by
8.10 km
End point
Parking
Way Types & Surfaces
Way Types
8.08 km
Surfaces
8.07 km
< 100 m
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Elevation
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Weather
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Today
Wednesday 26 August
25°C
12°C
0 %
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Max wind speed: 6.0 km/h
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This route was planned by komoot.
The Windsor Trail is located in Mount Ascutney State Park in Vermont. The trailhead is typically accessed from the park's entrance. Parking is available within the state park facilities.
Yes, as the Windsor Trail is located within Mount Ascutney State Park, there is an entrance fee required to access the park. No additional permits are typically needed for hiking the trail itself.
Dogs are generally permitted on trails within Vermont State Parks, including the Windsor Trail, but they must be kept on a leash at all times. Please ensure you clean up after your pet.
The trail is excellent for hiking from late spring through fall. Summer offers lush greenery and the chance to spot painted Trillium, while fall provides vibrant foliage. Winter hiking is possible but requires appropriate gear and awareness of conditions, as the trail can be steep and potentially icy.
The Windsor Trail is considered an Intermediate/Difficult hike, known as the steepest ascent up Mount Ascutney. It requires good fitness due to significant elevation gain, but the footing is generally good with no technical rock climbing involved.
The trail takes you through diverse scenery, including birches and pines, and follows a brook in its lower half. A notable feature is Gerry's Falls, a beautiful waterfall early in the hike. Near the summit, you'll find an Observation Tower on Mount Ascutney, offering 360-degree panoramic views of the White Mountains, Green Mountains, Berkshires, and Taconics.
The Windsor Trail itself is primarily an out-and-back route for reaching the summit of Mount Ascutney. However, it connects with other trails in the park, allowing for variations or longer loop possibilities if combined with other paths.
The terrain is varied. The lower half follows a brook and includes sections of a wide woods road. As you ascend, it becomes a challenging climb with good footing. You'll traverse through forests, past an old sawmill clearing, and alongside a ravine.
Yes, the route also passes through sections of the Norcross Trail, Castle Rock Trail, Brownsville Trail, and the 1903 Route, among others, offering opportunities to explore different parts of Mount Ascutney State Park.
Yes, there are two cold springs about two-thirds of the way up the trail. Additionally, you'll pass an old stone lean-to shelter that has a fresh drinking water spring, which can be a welcome stop during your hike.
Given its challenging nature, bring plenty of water, sturdy hiking boots, and layers of clothing suitable for changing weather conditions. Snacks, a map, and a first-aid kit are also recommended. If hiking in cooler months, be prepared for potentially icy conditions.
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