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Hiking Trails in Southern Vermont

Below are detailed descriptions of 7 hiking trails in our immediate area.

In addition to these local hikes, the Appalachian Trail is just a 20-minute drive from Deerhill Inn, and you can hike the Stratton Pond section of the Appalachian Trail, which in Vermont follows the same route as Vermont's Long Trail.

Dover/Wilmington Valley Trail

Covering both Dover and Wilmington, the Valley Trail starts 1 mile from Deerhill Inn, is moderate difficulty, and takes 2 hours - 6 hours. View the Valley Trail Map.

West Dover Crosstown Trail

A sub-section of the larger Dover/Wilmington Valley Trail, the Crosstown Trail is 1 mile from Deerhill Inn, is easy difficulty, and takes 20 minutes - 2 hours. View the Crosstown Trail Map.

Mount Snow

You can hike parts of the Mount Snow Ski Area, which is 6 minutes from Deerhill Inn, but it's mostly designed for mountain biking, is high difficulty, and takes 20 minutes - 3 hours. You can combine hiking with a scenic chairlift ride, depending on season and day of week. View the Mount Snow Trails Map.

Haystack Mountain

The Haystack Mountain Trail, a 15-minute drive from Deerhill Inn, is a high difficulty climb up to the summit of Haystack Mountain, and takes 4 hours. View the Haystack Mountain Trail Guide and Haystack Mountain Trail Map.

Molly Stark State Park

A Vermont State Park, Molly Stark is 15 minutes from Deerhill Inn and moderate difficulty. It takes about 90 minutes to get to a fire tower at the top of Mount Olga. View details of Molly Stark State Park and the Trail Map.

Woodford State Park

A Vermont State Park, Woodford is 30 minutes from Deerhill Inn and moderate difficulty. It takes about 2 hours to get around a reservoir. View details on Woodford State Park and the Trails Map.

Jamaica State Park

A Vermont State Park, Jamaica is 30 minutes from Deerhill Inn. A wide trail follows an old railroad bed along the West River up to a dam and waterfall. It's easy difficulty for 30 minutes leading up to Ball Mountain Dam and then moderate difficulty for another 15 minutes to Hamilton Falls. View details on Jamaica State Park and the Trails Map.

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