Discover Dummerston: History, Prospect Hill, and the Apple Pie Festival

Dummerston brings together local history in Dummerston Center, a scenic hike on Prospect Hill, and community events centered around the Apple Pie Festival. When choosing a destination for a hotel stay, these themes offer different starting points: you can focus on a visit to the Historical Society, a scenic outing, or a trip to a festival event.

Dummerston Center: Visit and Local History

The Dummerston Historical Society is located in Dummerston Center next to the Town Office. Admission is free. It is open on the first and third Sunday of each month from 1 to 3 p.m., or by appointment. The Center Schoolhouse was moved in May 1978 to make room for the Dummerston Historical Society. When the former schoolhouse is open, it offers a glimpse into Dummerston’s local history through genealogies, photographs from past exhibits, scrapbooks, artifacts, and albums. The society plans one to four public events each year, including photo and art exhibits, educational programs, and open houses.

Prospect Hill: Trail to the Summit Meadow

The hike up Prospect Hill begins in the historic village of Dummerston Center with a scenic 0.4-mile road walk. The Prospect Hill Trail leads to a large meadow at the summit of Prospect Hill, which is also called Blueberry Hill. The meadow offers a 180-degree view, including Mount Monadnock and Mount Snow. Prospect Hill and Blueberry Hill refer to the same summit, so both names lead to the same viewpoint. The trailhead route is described as a 0.4-mile stretch along the road, while the view is from the summit meadow.

Apple Pie Festival and Local Offerings

Another reason to visit is the annual Apple Pie Festival hosted by the Dummerston Congregational Church in Dummerston Center. A report on the 2025 edition describes it as the 56th edition and notes that visitors came from across the Northeast. Whole or sliced apple pies were offered that year, with Grafton Village Cheddar or ice cream available on request; fresh apple cider and cider doughnuts were also on offer. Offerings may vary from one edition to another. The 2025 program also included an arts and crafts market and a cookout hosted by the Evening Star Grange with more than 20 vendors. During the 2025 festival, the Dummerston Fire Department served an all-you-can-eat pancake breakfast at its station in Dummerston Center. If you plan your trip around the festival, check the date of the relevant edition.

When choosing your travel dates, you can focus on what interests you most: local history, the view from Prospect Hill, or an edition of the Apple Pie Festival.

Discover more destinations: Putney, Brattleboro, Rockingham, Stratton, Newfane, Whitingham, Wardsboro, West Dover

For the broader travel guide: Windham County.