Windham is a quiet mountain hamlet with wildlife and vintage charm
In South Vermont, Windham is a small but scenic town tucked in the rolling hills and valleys of the Green Mountains. Windham was settled around 1795, and after twenty years, the population tripled. Since then, however, there has been a slow decline, and today, slightly more than 400 residents live in this quaint Windham County town. The Windham Village Historic District features about a dozen Greek Revival buildings with historical significance, including the Congregational Church. Not much architectural change has happened since the village's 18th century founding, landing the community on the National Register of Historic Places in 1984.
The secluded environment of the area lends itself to several hidden hiking trails, and the landscape makes for backyard tributaries as waterways run down into the valley. A winding two-lane highway serves the rural community, breaking off into unmarked mountainside lanes where residences hide far from the main road. "People move here because it’s a quiet mountain town. We appreciate when people tread lightly and pick up their trash, not making a lot of noise or trespassing on their neighbor’s property,” says Alison Cummings, broker/owner with Cummings & Co who is the third generation to live on her family’s farm. “We respect nature here. We have a lot of mountain biking, hiking and nature conservancy with bear, moose and deer. Our ponds also see eagles and beavers. Outside of wildlife, we don’t have a lot of visitors. And that’s the way we like it.”
Hiking through state parks and events at the local meetinghouse
The elevation varies throughout Windham, as mountains extend above the horizon and valleys dip low into creeks and streams. That geographic variation allows for several state parks and trails in and around the town. On Windham’s south side, Hamilton Falls requires a moderate hike to a 50-foot cascade, where locals enjoy light swimming or picnicking. “It’s a spectacular three-level waterfall,” Cummings says. “And the brook that the falls pours into is the only Class-A water in the state of Vermont, running from Glebe Mountain all the way into the West River.” On the west side, Lowell State Park has a 3.5-mile hiking trail around Lowell Lake, which many nature lovers use for scenic kayaking adventures. To the east, Mollie Beattie State Forest offers wooded trails that are popular for summer hikes and winter snowshoeing.
The town’s Congregational Church, which was built in 1802 in the Greek Revival style, serves as Windham’s meetinghouse and nondenominational church. “The church has the highest steeple in the state of Vermont because of Windham’s elevation,” Cummings says. “We have different events there, like tag sales, chicken dinners and yoga classes. The town’s library is also in the building.” Cummings also mentions that the Windham Firehouse hosts periodic auctions, including a pie auction.
Cottages and Farmhouse Revivals for full-time and seasonal residents
Due to its small population and country environment, Windham has a low housing inventory. Interested buyers can find a range of homes from quaint cottage camp homes as small as 600 square feet and as large as Farmhouse Revivals with five bedrooms and 3,000 square feet of space. In between, there are rustic log cabins and New England colonial-style homes, as well asCape Cods and saltboxes. Some properties sit on an acre or two, while others are secluded on 25 acres with a creek or river flowing through the backyard. Price tags generally run from $125,000 for a studio cabin to $925,000 for a spacious farmhouse.
Due to its proximity to five different ski resorts, many Windham residents are second-homeowners. “We’re equidistant to Bromley, Magic, Stratton, Okemo and Mount Snow,” says Cummings. “Windham is a great place for people into winter sports. We have about the same number of full-time residents and seasonal residents, but we’re enjoying a bit of a surge in full-time purchases because the price point is much lower and more affordable for our local families.”
Dine and attend farmers markets in Londonderry and Townshend
Windham's rural landscape may make for secluded residences and green spaces, but the town’s retail is absent. “We’re up in the mountains, so it’s an 11-mile drive for me to get to the grocery store,” Cummings says. “We go to Londonderry for errands, and we go to Grafton to have dinner.” To the west, Londonderry has a small shopping plaza with the Londonderry Village Market, a fresh grocery store. The town hosts the West River Farmers Market each Saturday, complete with artisan foods and craft vendors. To the east in Grafton, the 1801 Tavern offers a rotating farm-to-table menu. To the south in Townshend, West Townshend Country Store is a rustic food market in a former Victorian home that offers breakfast all day. Outside the store each Friday, the Townshend Farmers Market attracts a crowd for live music and local produce.
Students start at Townshend Elementary before Leland and Gray
Windham Elementary School used to serve the kindergarten through sixth-grade learners in the area before it shuttered in 2024. Reluctant town voters agreed that their students needed a larger, safer learning environment, as well as licensed educators. The 15 students that attended the school were then moved to Townshend School, where they will remain until further notice. Townshend School receives a B-plus rating from Niche and has about 90 students in attendance. Learners can then advance to Leland & Gray Middle and High School, which receives a C-minus. This combined school, built in 1834, serves around 250 students in sixth through twelfth grades from the towns of Windham, Newfane, Brookline, Jamaica and Townshend. In addition to traditional athletic teams, Leland & Gray offers a co-ed snowboarding team.
Artistic retreats and scenic inns hide in Windham’s mountainside
Residents and visitors alike use Windham’s open green spaces for tranquil retreats and artistic inspiration. The Fourth Corner Foundation, located on the town’s north side, aims to help artists create alongside nature. “It was originally dedicated to sustainable building practice research,” says Matt Brader, Executive Director of The Fourth Corner Foundation. “We are now transitioning to lodging for artists in their 30s who can focus on restoring the four magnificent buildings on our property, and in return, they’ll get a free place to stay and support on different skills and trades.” The nonprofit organization’s campus also includes horticulture gardens and about 3,000 square feet of gallery space. “I leave it open for people to wander the gardens, but they need to schedule a tour with me if they want to look around inside the buildings,” Brader says. “We support other local nonprofits by offering our venue for them to run their events. We also have a big annual art show for the community.” A few historic inns and renovated chalets offer bed-and-breakfast services, including Windham Hill Inn, which is a former dairy barn from the 1800s that sits on 160 acres overlooking the Green Mountains.
Windham Hill Road winds through the car-dependent town
Windham Hill Road serves as the town’s main thoroughfare, running north-south through Windham and connecting residents to Vermont Route 11 at the north end and Vermont Route 30 at the south end. These state highways make for a 90-mile commute to Albany, a 115-mile commute to Hartford and a 140-mile commute to Boston. “We use Bradley International Airport in Hartford because it’s the easiest to get there,” Cummings says of the airport just over 100 miles south. “I travel a lot, and I can fly pretty much anywhere from there with a connection.”
Written By
Mary Beth Greene
