Scott Covered Bridge in Townshend, VermontPhoto Credit : Oliver Parini
Bustling with bookstores, ethnic restaurants, and galleries spotlighting the work of local artisans, the lively town of Brattleboro anchors this 100-mile loop that takes in some of southern Vermont’s loveliest villages. It’s a drive that begins with a vivid reminder of why Vermont roadways meander the way they do—it’s because they follow rivers and streams, the way the state’s earliest settlers did. Brattleboro lies on the Connecticut River, at the point where the West River meets that broad waterway, and Route 30 hugs the West for much of this drive.
Setting out from Brattleboro, the first village you’ll encounter along the way is Newfane, the “shire town” (Vermonters’ term for county seat) of Windham County since 1787. Anchored by a classic town green, it’s a place that looks as if its clocks stopped before the Civil War. Townshend and Jamaica, tiny towns that give their names to nearby state parks, stand at the threshold of the vast Green Mountain National Forest. Just past Townshend, Route 30 joins Route 100, which splits away to rejoin the West River and cross it at South Londonderry. Ahead lies Weston, a hill town whose fame long surpassed its size because of two venerable institutions: the Weston Playhouse and the Vermont Country Store.
The route leaves the West River and Route 100 behind, taking Chester Mountain Road —with a fiddler’s-elbow turn—into Chester, where Scottish masons long ago created a “stone village” that oddly stands apart in a state known for quarrying granite but where wood for building houses was always closer at hand. Chester has a village green, too, stretched into a narrow mall that accommodates inns and cafés.
Head south on Route 35 to Grafton, a town reclaimed from obscurity by a forward-thinking nonprofit and by one of Vermont’s oldest artisan food traditions, cheesemaking. Next, wander down Route 121 along Saxtons River for the town named after it, and jog north to Rockingham for a look at Vermont’s oldest unchanged buildings—and, perhaps, its most serenely beautiful.
South along Route 5 at Bellows Falls, Vermonters’ penchant for revival and reuse comes across in an old railroad and canal town that’s been stylishly snapped out of its doldrums—in this case, by the grit and imagination of local artists and entrepreneurs. And in Putney, a few miles south on the way back to Brattleboro, there’s an outpost of one of the oldest entrepreneurs of all: Santa Claus.
Vermont Artisan Designs, Brattleboro: Pottery, glass, fiber art, furniture, and galleries devoted entirely to fine art and photography make this a must-visit before you hit the road.
Andrea’s Table, Newfane: To the rear of the c. 1825 Windham County Courthouse is the elegant Four Columns Inn; its new restaurant, Andrea’s Table, features a farm-to-table menu worth catching Wednesday through Saturday evenings.
Jamaica State Park, Jamaica: Tucked along a bend of the West River, this park offers trails to Ball Mountain Lake and Hamilton Falls, an impressive series of pools and cataracts.
D. Lasser Ceramics, Londonderry: Spilling onto the lawn of Daniel Lasser’s Route 100 studio and showroom are sculptures, tableware, and garden ceramics in a vividly expressive palette of colors and vocabulary of designs.
The Vermont Country Store, Weston: In an homage to his grandfather’s general store in northern Vermont, Vrest Orton put together a mail-order catalog of classic, durable items and opened a store in 1946 to go with it. The store still occupies its original premises in Weston, purveying hard-to-find old-time products, Vermont foods, and too much more to mention.
Chester: Inn Victoria and the Fullerton Inn are possible overnight choices, the first for its Victorian luxe and the second for feeling more like a small country hotel, which it’s always been. Spending the night in Chester or not, it’s pleasant to enjoy lunch on the Fullerton’s veranda—or, if a picnic is more in order, to stock up on cheese and charcuterie at Bushel and a Peck, down the street.
Grafton: During the 1960s, the Windham Foundation remade this entire town into the apotheosis of a New England village. The centerpiece is the foundation-owned Grafton Inn, occupying a grand colonnaded structure that was built in 1801. Also under the foundation umbrella is the Grafton Village Cheese Company, a crafter of fine cheddar since 1892.
Rockingham Meeting House, Rockingham: In 1787 the townspeople of Rockingham erected a meeting house, and in all the years since, it’s never been altered, inside or out. Open to visitors daily, it may be the most serene spot in Vermont.
Windham Antique Center, Bellows Falls: In the heart of Bellows Falls is this warren of rooms filled with vintage furniture, porcelain and silver tableware, heirloom jewelry, lamps, and restoration hardware—plus an unexpected sideline, a natural history collection that includes geodes bursting with color.
Curtis’ All-American Barbecue, Putney: Curtis Tuff was a local culinary legend for over 40 years; since his 2020 passing, his daughter Sarah has kept at the job of long, slow smoking and serving “till sold out.” Pork ribs and pulled chicken are the mainstays here, with traditional sides like yams, collard greens, and corn muffins.
Santa’s Land, Putney: A roadside attraction since 1957, this is the place to meet Santa and his elves, ride a Christmas-themed train and carousel, play mini golf, and navigate a funhouse. Open weekends from late July through Christmas, it’s not high-tech—just sweet old-fashioned fun.