Londonderry is a scenic commercial and community center in southern Vermont
Country roads like State Routes 100 and 11 crisscross the Green Mountains in southern Vermont, intersecting in deep country towns and villages like Londonderry. Transitioning first from an agricultural community into one centered around industry and railroad tracks along the West River, Londonderry has carried over its historic trappings while transitioning into something of a modern business center for an overwhelmingly rural region. “Londonderry is unique in that they have a little commercial strip with a marketplace, a bike repair shop, places to go out to eat – it's a little bit more of a hub. That gives it a pretty 50-50 split between fulltime residents and second homeowners,” says Carrie Mathews, a broker at Winhall Real Estate with more than 20 years of experience specializing in south central Vermont. The aesthetics of classic New England small-town life fill the riverside valleys found in Londonderry, set against forested slopes that remain rich with opportunities for outdoor recreation as the trees shift from green to red to white and snow-covered.
Public and private recreation from the Green Mountains to the West River
The Green Mountains are as well known for publicly accessible recreation like the Long Trail as they are for private ski resorts, including Londonderry’s own Magic Mountain Ski Area and the slightly more distant Stratton Mountain Resort. Those that prefer cross-country to alpine skiing might instead head to the forested trails at the Viking Nordic Center. Fishing and paddling in the water at Lowell Lake State Park are best enjoyed through the warmer months, but hikers can simply swap their boots for snowshoes to hit the park’s trails through all four seasons. The West River winds through Londonderry, itself a hub for boaters and anglers. The route of a former regional railway hugged the river’s banks; now, cyclists travel long distances between rural Vermont towns on the West River Trail. “The West River Railroad ran from Londonderry to Brattleboro – they used to call it ‘36 Miles of Trouble’ because it always broke down,” Mathews says. The rail trail is still working on connecting all 36 miles, but hikers and bikers can still access many miles of the upper trail system from the town’s trailhead.
Single-family homes built since the colonial era
Simple colonial and folk homes were built on rural roadways and farmsteads in the late 1700s and early 1800s, many of which have been updated and preserved into the modern day. Londonderry’s longstanding appeal as a mountain town means that new houses were built in a mix of styles in the centuries since, including rustic cabins, simple midcentury Cape Cods and contemporary custom builds with much larger floorplans. Prices for single-family homes can range from around $200,000 for a small, simple cottage in a densely plotted village to over $1 million for an expansive estate set on a rural acreage. Londonderry’s median single-family home price is around $490,000, higher than the national median of roughly $400,000. Condos are less common and can go for anywhere from $190,000 to nearly $2 million depending on their size, luxury amenities and proximity to ski resorts.
Shopping and dining in Londonderry’s villages
State Routes 100 and 11 connect the small villages that make up the densest commercial districts throughout the town. Londonderry’s namesake village is the largest, centered by a locally owned grocery store, the Londonderry Village Market. Set in the same strip mall, shoppers might browse albums at In the Moment Records or pick up some household essentials at Londonderry Hardware. “The Second Congregational Church has the Thrifty Attic store – that's a very popular place for drop-off and pick-up,” Mathews says. Diners can enjoy New American cuisine in the historic dining room of SoLo Farm & Table or opt for the hearty diner fare served at Maple Leaf Diner.
Farmers markets and local community centers around Londonderry
While agriculture is no longer as big in Londonderry as it was in the past, the town still prides itself on supporting its modern farmers. Residents can savor locally grown produce and fresh baked goods while enjoying live music at the West River Farmers Market on Saturdays through the warmer months. Although its hours are limited, the South Londonderry Free Library is a hub for bookworms and residents looking to attend a family-friendly craft or gardening class. History buffs will usually need to schedule time with the Londonderry Arts and Historical Society to visit their museum, a repository of local artifacts and artworks displayed in a farmhouse and barn built in the 1800s.
Traveling to regional employers and more distant hubs like Rutland and Brattleboro
The local ski and tourism hubs are some of the largest employers in and around Londonderry. Residents can get some medical care at Mountain Valley Health Center, but Springfield Hospital offers more comprehensive care about 20 miles away down State Route 11. Brattleboro and Rutland are both more than 30 miles away, each home to a larger hospital and town center. Southern Vermont Regional Airport offers direct flights to Boston Logan International Airport about 25 miles from home. Londonderry is not served by public transportation, so residents will need a personal vehicle to get around.
Attending Flood Brook School and nearby independent upper schools
Flood Brook School serves prekindergarten through eighth grade and earns a B from Niche. The Green & Taconic School District does not operate any high schools, so students will likely finish at an independent school through the state’s school choice program. A-rated Long Trail School is an option that has a tuition sending relationship with Londonderry, located in the town of Dorset. The town will partially cover the cost of tuition, and students there frequently get to travel around the country and hike nearby trails thanks to the school’s experiential learning focus.
Flood risk along the West River
While Londonderry owes its development and wealth of recreation to the West River, that watershed has also caused significant flood damage to the town over the years, most recently in 2023. Run-off from the hills and high water after unusually heavy rain can damage roadways and homes. Residents should check maps to understand their potential risk and need for flood insurance. A town-backed committee is also working to form future flood resiliency plans.
Written By
Julia Szymanski
