Chesterfield's rural feel, scenic vistas and close-knit community
The small town of Chesterfield may sit among the rolling hills and historic covered bridges of southwest New Hampshire, but this community of 3,500 is as defined by its access to neighboring urban amenities as it is its rural landscape. "Chesterfield is right between Keene and Brattleboro," says Laurie Mack, a local Realtor with Better Homes and Gardens-The Masiello Group. "No matter where you are, you're only 10 miles from Interstate 91. We're basically in the hub of central New England, so you can get to Maine, Boston and Hartford within two hours."
This community, founded in the mid-18th century, has a long history reflected in its classic New England architecture, historic farmhouses and houses of worship like Asbury Church. It's charm lies in its quiet rural character, scenic vistas and close-knit community. Residents are surrounded by outdoor recreation, from wooded hiking trails to paddling on Spofford Lake, while still only a short drive from shopping, dining and entertainment options in Brattleboro and Keene.
Trails, forests and lakefront beaches offer year-round adventure
Preservation lands, mountain peaks and the wide-open countryside surround Chesterfield. Spofford Lake anchors the town's summer activities, enticing swimmers, boaters and kayakers to explore its 732 acres. A small yacht club, boat ramp, summer camp and two small beaches dot its shores: Wares Grove and North Shore.
A network of trails and nature preserves crisscross the region, inviting hikers and bikers to wander beside tranquil ponds and creeks. The Chesterfield Gorge Natural Area beckons visitors with its dramatic ravines and tranquil forested trails along the northeast corner of town. Friedsam Memorial Park offers additional trails in the heart of town. Farther west, a hiking path along the Connecticut River meanders toward the Wantastiquet Mountain Natural Area, a 520-acre forest where sweeping river valley vistas reward those who make the climb. The adjacent Madame Sherri Forest features dog-friendly trails and historic stone ruins.
Chesterfield is also the home to Pisgah State Park, New Hampshire's largest state park with 13,300 acres of rough forested terrain, wetlands and highland ridges. With six trailheads offering year-round access, Pisgah is a destination for hikers, mountain bikers, ATVers and snowmobilers. The park is a hub for community events led by Friends of Pisgah, who host guided hikes, annual kayaking trips and the Pisgah Mountain Trail races. "We're also close to all of Vermont's ski resorts," Mack says.
Colonial homes, cabins and cottages tucked into wooded lots
Chesterfield is defined by a network of quiet roads connecting small neighborhoods, scenic landscapes and modest parcels of land priced between $100,000 and $300,000. Secluded enclaves are hidden behind the tree line, with 20th- and 21st-century ramblers, log cabins, lakeside cottages and colonial-style homes ranging from $250,000 to $450,000. Larger Colonial Revivals, custom-built designs and lakefront homes can sell from $450,000 to $750,000, with a select few fetching price tags over $1 million. Most properties date from the mid-to-late 20th-century through the present day, though a handful are still standing from the mid-18th century. Chesterfield also boasts a CAP Index Crime Score of 1 out of 10.
Educational offerings around Cheshire County
New Hampshire School Administrative Unit 29 is composed of seven independent districts. The Chesterfield School District is home to just one school—Chesterfield School—a K-8 institution that garners a C rating from Niche. Older students may then attend Keene High School, which earns a B-minus and offers a robust list of Career and Technical Education pathways, from business and information technology to TV and film production. Regarding higher education, Cheshire County offers several colleges and universities within commuting distance, including Keene State College, Antioch University and River Valley Community College.
Small-town eateries and additional amenities in Brattleboro and Keene
Several commercial warehouses and outlet stores, including a state-run liquor store, line New Hampshire State Route 9 on the west side of town. "Chesterfield Inn's restaurant is the only real eatery in town," Mack says, serving up seasonal fine-dining dinner fare. Down the road, Village Creamery is known for its generous scoops, brownie sundaes and creamy milkshakes. Barn and Thistle is a whimsical gift shop and eatery in the neighboring town of Westmoreland. Inside, a cozy cafe serves hearty breakfasts, fresh salads, sandwiches, homemade baked goods and shelves brimming with unique treasures.
Residents can peruse fresh produce, meats and handcrafted goods at the seasonal farmers market, held at the town hall from May to October. For larger shopping needs, residents venture to nearby towns. Keene and Brattleboro are equidistant from town, offering a variety of chain grocers, big-box retailers and mom-and-pops.
Commuting around Chesterfield
Chesterfield is a rural, car-dependent community, with New Hampshire State Route 63 and State Route 9 running through town. Cheshire Medical Center is about 12 miles east, while Brattleboro Memorial Hospital is 12 miles southwest. Bradley International Airport is about 88 miles south via Interstate 91. Nearby roadways offer convenient access to larger cities, with Boston just 100 miles southeast, while Brattleboro's Amtrak line links the region to destinations as far as Washington, D.C.
