Routes

Planner

Features

Updates

App

Login or Signup

Get the App

Login or Signup

Routes
Hiking trails & Routes
United States
Vermont
Windsor County

Windsor Trail

Moderate

4.6

(5508)

17,951

hikers

Windsor Trail

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

A

Start point

Parking

Get Directions

1

1.17 km

Gerry's Falls

Highlight • Waterfall

Gerry's Falls is one of five seasonal waterfalls dotted around the slopes of Mount Ascutney. The water flows down exposed bedrock and boulders between ferns, and then cascades into a waterslide.

Tip by

2

3.98 km

Trails from all directions lead to the summit of Mount Ascutney. There's a lookout tower that takes you above the trees for great views.

Tip by

B

8.10 km

End point

Parking

Loading

Way Types & Surfaces

Way Types

8.08 km

Surfaces

8.07 km

< 100 m

Sign up to see more specific route details

Sign up for free

Elevation

Elevation

Nothing selected – click and drag below to see the stats for a specific part of the route.

Sign up to see more specific route details

Sign up for free

Weather

Powered by Foreca

Today

Wednesday 26 August

25°C

12°C

0 %

Additional weather tips

Max wind speed: 6.0 km/h

to get more detailed weather forecasts along your route

Comments

guide_signup

Want to know more?

Sign up for a free komoot account to join the conversation.

Sign up for free

This route was planned by komoot.

Save

Edit route

Download GPX

Move start point

Print

Share

Embed on a website

Report an Issue

Report restricted access

Frequently Asked Questions

Where is the trailhead for the Windsor Trail and what are the parking options?

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.

Are there any fees or permits required to hike the Windsor Trail?

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.

Is the Windsor Trail dog-friendly?

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.

What is the best time of year to hike the Windsor Trail?

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.

How challenging is the Windsor Trail?

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.

What kind of scenery and points of interest can I expect on the trail?

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.

Is the Windsor Trail a loop or an out-and-back route?

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.

What is the terrain like on the Windsor Trail?

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.

Does the trail intersect other well-known paths?

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.

Are there any water sources or shelters along the trail?

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.

What should I bring for a hike on the Windsor Trail?

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.

Nearby routes

Moderate

11

Smith Pond Loop Trail

02:50h

9.21km

330m

Explore
RoutesRoute plannerFeaturesRedeem a voucherHikesMTB TrailsRoad cycling routesBikepackingSitemap
Download the app
Follow Us on Socials

© komoot GmbH

Privacy Policy