Winchester is a small town with rural appeal
Incorporated in 1753, Winchester is a small, rural town tucked into the southwestern corner of New Hampshire. The area is bordered to the south by Massachusetts and to the west by Vermont, and is equidistant to Keene and Brattleboro, each about 13 miles away. As of the 2020 census, Winchester was home to just over 4,100 full-time residents. “People are really drawn to this area for the historic aspect, the space you get and all the nature you can explore here,” says Diana Elfreich , a local real estate agent with Keller Williams Metropolitan and resident of the neighboring town of Swanzey. Winchester is home to two historic covered bridges: Ashuelot and Coombs, both well-known photo-taking attractions in the Monadnock region. Winchester has an overall CAP Index Crime Score of 2 out of 10, lower than the national average of 4.
Historic New England homes meet modern builds
Winchester’s housing landscape includes everything from manufactured homes and ranch styles to historic New Englanders and new builds that feature a mix of contemporary and Colonial Revival architecture. Homes in central Winchester typically have much smaller lots than rural properties in the town’s countryside, which often occupy more than an acre of land. Turnkey single-family houses typically cost between $160,000 and $550,000, with a median sale price of just under $400,000. Manufactured homes are often less expensive in comparison, with prices ranging from about $40,000 to $200,000.
Winchester School serves K-8
Kindergarten through eighth-grade students are zoned for Winchester School, which receives a C-minus rating from Niche and is the only school in town. Grades nine through 12 can attend the B-minus-rated Keene High School, which is part of the Keene School District and a 20-minute drive from Winchester. The high school offers over 30 student clubs and 21 athletic teams, including skiing, bowling and bass fishing. High school students can also take Advanced Placement courses or do dual enrollment programs through several higher education avenues, including Cheshire Career Center and Keene State College.
Monadnock region offers year-round outdoor recreation
Winchester residents can enjoy outdoor recreation throughout all four seasons with access to several well-known outdoor destinations. Granite Gorge Mountain Park is about a half-hour drive away and has ski hills and other winter sports amenities just outside Keene. While Granite Gorge Mountain may be the nearest place for downhill skiing, Winchester residents can easily get to cross-country ski trails in Pisgah State Park, which takes up part of the western side of town. Covering more than 13,300 acres of land, Pisgah State Park has an extensive nature trail network that, in addition to cross-country skiing, can accommodate hiking, biking, snowmobiling and off-roading vehicles, depending on the season. Other outdoor destinations in town include Pulpit Falls, a natural waterfall attraction at the end of a hiking trail, and the Ashuelot River, which winds through Winchester and is popular for activities like kayaking and fishing. Golfers can practice their swing at Willy D’s Driving Range, just off Route 10.
Local businesses and farms dominate shape shopping and dining
Winchester’s shopping and dining amenities are limited, though the local establishments typically reflect the town’s welcoming, rural atmosphere. Winchester’s countryside is dotted with small farmers’ markets like Cheshire Garden, which sells handmade goods and seasonal fresh produce. The town center has a convenience store called Main Street Mini Mart and Kulick’s Market, where residents can shop for weekly groceries. Aubuchon Hardware sells hardware tools, farm machinery and other industrial supplies. Winchester’s restaurant options are mostly locally owned places like The Rustic Table and The Arlington Inn & Tavern, a casual pub-grub spot attached to a bed and breakfast in a historic property from the early 1800s. Takeout options are available at Win Win Express for Chinese fare and Dunkin’, the town’s only chain restaurant.
Racing events and the Winchester Pickle Festival bring crowds to town
Winchester's thriving motorsport scene stems from Winchester Speed Park and Monadnock Speedway, two racing venues in town. Winchester Speed Park is known for its motocross events, while Monadnock Speedway hosts NASCAR Whelen Modified Tour races and other modified relays. Speedways aren’t the only thing to attract crowds to town, though. “Winchester has the Pickle Festival every year in September, and it’s one of those things you can’t miss,” Elfreich says. For more than 25 years, the Winchester New Hampshire Pickle Festival has attracted several thousand attendees annually. The festival starts with the Pickle Parade, followed by a day full of contests and competitions, live music performances and family-friendly entertainment.
Car-dependent commuting in Cheshire County
Winchester is a car-dependent community without any public transit systems. A few numbered thoroughfares—New Hampshire Routes 119, 78 and 10—run through town, all converging along Main Street in the center of Winchester. Commuters can take Route 10 and drive 20 minutes north to Keene or take the route south and reach the Massachusetts state line in under 10 minutes. Route 119 travels west across the Connecticut River and up to Brattleboro, Vermont, roughly 13 miles away. The nearest commercial airport is Manchester-Boston Regional Airport, nearly 60 miles from Winchester. The equidistant Brattleboro Memorial Hospital and Cheshire Medical Center have 24-hour emergency departments and are less than half an hour drive away.
