Mt. Ascutney via the Windsor Trail

Mt. Ascutney – Windsor Trail – Vermont

For our first real hike since the beginning of the Covid-19 pandemic, we drove over to Vermont for a half-day hike to the summit of Mt. Ascutney. We had previously seen the mountain a few times in the distance from St. Gaudens National Historic Park, and it had been on our short list of New England day hikes to try out with Baxter. Since Mt. Ascutney is considered a “monadnock” (isolated mountain located in an otherwise level area), it is an iconic view in this region of Vermont/New Hampshire. It is also one of the premier hang gliding spots in New England. While there are four trails leading to the summit of Ascutney, we decided to go with the Windsor Trail, the most direct but steepest option for ascent.

Trail Summary (Windsor Trail)

Summit Elevation: 3,144 ft.

Elevation Gain: 2,520 ft.

Distance: ~5.6 miles (out and back)

Difficulty: Moderate

Blazes: White

Trail Map

Getting There

The small parking area at the trailhead for the Windsor Trail is located on Back Mountain Rd. (Rt. 44A) just west of I-91. It is a ~7 minute drive from the Windsor town center, ~30 minutes from Hanover, NH, and ~2 hours from the Boston area.

The Windsor Trail

The trail begins in a meadow with a view of the summit off in the distance. From there, the trail enters the woods and begins what ends up being a consistently steep ascent. It isn’t terribly difficult, but it is constant. There are basically no flat sections of the trail until the final approach to the summit. The first mile of the trail is effectively a straight line with a steep drop off to the left and a stream running parallel to the trail.

After about 0.8 miles there will be a short spur to the left leading to Gerry’s Falls. The falls are small but it’s a scenic spot to take a break (if you’re a human) or go for a swim (if you’re a dog). Baxter enjoyed himself thoroughly.

mt. ascutney Windsor trail Vermont
Gerry’s Falls



Shortly after Gerry’s Falls, there is a stream crossing before the trail branches off to the right and continues climbing. After another mile, you will reach a trail junction. If you go to the right, you will arrive at a log shelter built in 1968 (we went this way). Alternatively, if you go to the left, you will have the option of taking a 0.1 mile spur to a lookout point called Blood Rock. Regardless of which way you go, both branches rejoin after about a quarter of a mile. Shortly after the two branches rejoin, you will reach a junction with the Futures Trail on the left followed shortly by a junction with the Castle Rock Trail and Brownsville Trail. There is a 0.1 mile spur to an overlook at Castle Rock overlooking the Connecticut Valley and another spur to an overlook at Brownsville Rock with views to the northwest.

mt. ascutney Windsor trail Vermont
Baxter looking for leftovers in the log shelter

The Summit

The Windsor Trail and the Brownsville Trail run together for the final 0.2 miles of the ascent. Before reaching the official summit, you will come to a ~25 foot observation tower. There are only modest views from the base of the tower which is still below the tree line, but the tower is high enough to provide 360-degree views of the surrounding area including multiple Vermont ski mountains like Okemo and Killington. The true summit is much less impressive. It is just a rocky area with two large radio towers and minimal views.

Read More: Best Hikes in New England

mt. ascutney Windsor trail vermont
Panoramic view from the observation tower



mt. ascutney Windsor trail Vermont
View from the observation tower
mt. ascutney Windsor trail Vermont
The true summit offers minimal views

 

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