Mt. Ascutney – Windsor, Vermont

There are four main trails that lead to the summit of Mt. Ascutney.

The Weathersfield Trail — This trail is on the south face of the mountain, the base of this trail is located in a parking lot at the end of Cascade Falls Rd, off of Vermont Route 131 in Weathersfield. A main feature of this trail includes Cascade Falls which is the largest waterfall on the mountain.

The Windsor Trail — The parking area for the Windsor Trail is located on Back Mountain Road (Rt. 44A). This trail merges with the Brownsville Trail near the summit and passes by Gerry Falls, The Blood Rock Trail, and the Log Shelter.

The Brownsville Trail — This trail begins at a parking area along Vermont Route 44. The lower end of the trail follows an abandoned logging road up to an old granite quarry and the trail offers many good viewing opportunities to the north and west.

The Futures Trail — This trail is not officially maintained by the ATA and is maintained by Ascutney State Park, The trail begins in the campground at Mt. Ascutney State Park on Route 44A. This is the longest trail on Mt. Ascutney — 4.6 miles, covering a wide variety of forest and geography before it connects to the Windsor Trail near the summit. Highlights of this trail include Bare Rock Vista (1.0 mile) and the Steam Donkey — a steam powered machine used for cable logging in the early 1900s (3.5 miles).

This trail can also be accessed at two points along the State Park Mountain Road for a shorter hike to summit. At the top, a relatively level trail follows the ridgeline and crosses the summit.

The top of the mountain is well below the tree line and is therefore covered in forest, however a number of rocky cliffs allow good viewing, and there is an observation tower.

The summit can also be reached via a short trail from the parking lot at the end of the only road up the mountain, the Mt. Ascutney State Park Mountain Road.

Mt. Peg – Woodstock, Vermont

The trailhead to Mt. Peg is easily accessible from the Village Green. Head down Court St. between Courthouse and Woodstock Inn. At the end of Court St. turn left and then make a right on to Golf Ave. Continue on Golf Ave. to Maple St. At Maple and Golf Streets you may park on the left and the trailhead is to the left of the driveway.

Trail starts with a steep incline through the woods but then levels off and becomes a pleasant easy-going hike. The views from the summit include Mt. Tom, Billings Farm, the Pomfret Hills and Killington Mountain.

Mt. Tom – Woodstock, Vermont

Mt.Tom is a great hike as it affords a great view of the Ottauquechee River Valley and the Village of Woodstock. It is a small mountain that is essentially right in the middle of town. The main trail from the center of Woodstock Village is the Faulkner Trial. This is an easy to navigate trail and will take a hiker about 30 minutes. There are many switchbacks so the incline for most of the hike is very gradual. Note that the trial is steep, narrow and rocky for the last 100 yards.

The Long Trial & The Green Mountain Hiking Club

The Green Mountain Hiking Club is very active and organizes many hikes throughout the year. The Green Mouintain Club was responsible for building The Long Trail follows the main ridge of the Green Mountains from the Vermont-Massachusetts border to the Canadian border. It crosses Vermont’s highest peaks. Moreover, The Long Trail was the inspiration for the Appalachian Trail which coincides with it for one hundred miles in the southern third of the Vermont.

The Long Trail is a 273-mile hiking footpath. It also is associated with 175 miles of side trails and 70 primitive shelters The Long Trail offers endless hiking opportunities for the day hiker, weekend overnighter, and extended backpacker. Please feel free to visit the website of the Green Mountain Club to learn more.

The Ottauquechee Chapter of the Green Mountain Hiking Club Maintains their own calendar showing dates and times of hikes in the Woodstock-South Woodstock Area. To view this calendar click here.

There are many other trails in the Woodstock-South Woodstock area. Please feel fee to ask us.