10 Prettiest Towns In Vermont
Few places change costume as dramatically as Vermont. Green hills in summer give way to the loud oranges and reds of fall, then snow-hushed villages in winter, then meadows full of wildflowers in spring, and the state looks postcard-ready in every one of them. Pair that scenery with a stock of white-steepled, covered-bridge villages that have barely changed in a century, and you get some of the prettiest small towns in the country. These ten are the ones worth pointing the car toward, whatever the season.
Woodstock
If you have ever seen a photo of a Vermont covered bridge, odds are it was Woodstock's. The bright-red Middle Covered Bridge, built in 1836, crosses the Ottauquechee River right in the middle of the village, a short walk from a green ringed with Federal-era homes. This is the town most people picture when they picture Vermont, and it earns it. Billings Farm and Museum, a working dairy just outside the center, shows farm life as it ran in the 1890s and scoops some of the best creemees around.
Across the road, the Marsh-Billings-Rockefeller National Historical Park is the only national park that tells the story of land conservation, with carriage roads winding up through old-growth sugar maples to overlooks above the village. Come fall, the whole town glows, and downtown fills with people trading the covered-bridge photo for a table at one of the tavern kitchens. Woodstock is small enough to cross on foot and pretty enough that you will want to do it twice.
Stowe
Stowe wraps a classic white church steeple, a walkable Main Street, and the highest peak in the state into one very photogenic package. Mount Mansfield rises right behind the village, and the Stowe Recreation Path runs 5.3 paved miles along the West Branch with the mountain in view the whole way, flat enough for a stroller and pretty enough to walk twice. A few minutes south, the Gold Brook Covered Bridge, built in 1844 and better known as Emily's Bridge, is the town's lone surviving 19th-century covered bridge and its favorite ghost story. In fall the foliage here is some of the most photographed in New England, and the village keeps its looks straight through the ski season.
Waitsfield
Half an hour southwest of the capital, Montpelier, Waitsfield packs a lot of Mad River Valley beauty into a town of barely 1,700. Historic homes turned inns line the roads just outside the center, among them the Waitsfield Inn and the Hyde Away Inn, so you have plenty of places to land. Winter puts you minutes from the ski slopes at Sugarbush and Mad River Glen, and the warmer months open up waterfalls like Warren Falls, a run of ledges and pools that fills with locals on a hot afternoon. A little farther out, Camel's Hump State Park and Mount Mansfield State Forest deliver the big green Vermont backcountry.
Grafton
Grafton is a preserved 19th-century village of about 700 people, and much of that preservation was deliberate: a private foundation spent decades restoring the town to its historic look. The payoff is a walkable center full of generational small businesses. Stop at Plummer's Sugar House to taste local maple syrup and see the groves it comes from, and at Grafton Village Cheese Company for the cheddar the town is known for. Outside the village, trails run from the Grafton Trails and Outdoor Center, and the Grafton Inn, right in the center, has been putting up travelers since 1801. It is the kind of place where the whole point is to slow down.
Ludlow
Ludlow sits in south-central Vermont's Windsor County, in the heart of the Okemo Valley, and it makes an easy base for a season of activity. Okemo Mountain Resort rises right at the edge of the village for skiing and riding in winter, while the surrounding Green Mountain National Forest and Coolidge State Forest fill in the warmer months with trails like the Slack Hill hike. Come summer, Camp Plymouth State Park and its clear Echo Lake are the place to beat the heat. Downtown keeps its 150-year-old village bones, plus the Green Mountain Sugar House and the Ludlow Brewing Company for when the boots come off.
Quechee
Quechee sits along the Ottauquechee River and mixes natural drama with some of the best craft work in the state. The must-do is the Simon Pearce mill, where glassblowers work the furnaces in full view over the river and the restaurant upstairs plates dinner on the glass made downstairs, all powered by the same dam. It is worth an entire afternoon, inside and out. Just up the road, Quechee Gorge, Vermont's deepest at about 165 feet, drops away beneath the Route 4 bridge, with a trail down to the water. Round out the day at galleries like the Glenn Suokko Gallery before heading back toward the covered bridge by the old mill.
Middlebury
One of Vermont's larger towns at just over 9,000 people, Middlebury still feels like a village, with a waterfall tumbling right through its downtown. Founded in 1761, it holds beautiful old buildings like the Emma Willard House and the home of the Henry Sheldon Museum of Vermont History. It is also home to the quirky Vermont Experimental Cold Hardy Cactus Garden, which is exactly as odd and fun as it sounds. Just outside town, the Lincoln Peak Vineyard pours tastings through the summer, and reservations are smart since it is a popular road-trip stop. Add Middlebury College's handsome campus and you have a town that rewards a slow wander.
Manchester
Manchester has been a summer town since the 1800s, and it still has the marble sidewalks to prove it. The centerpiece is Hildene, the 412-acre estate Robert Todd Lincoln, Abraham Lincoln's son, built in 1905; the Georgian Revival mansion still holds one of the president's stovepipe hats, and the formal gardens go off when the peonies bloom in June. Just north of town, in East Dorset, Emerald Lake State Park surrounds its namesake green-tinted lake, set in the narrow valley between the Green and Taconic Mountains and good for a swim or a paddle.
In the village itself, the shopping runs from high-end outlets to the Northshire Bookstore, a Vermont institution people plan afternoons around, and the Inn at Manchester runs a covered-bridge tour if you want the history with your scenery. Between the mountains, the marble, and the Lincoln estate, Manchester earns its long-running reputation as one of the prettiest corners of southern Vermont.
Montgomery
Tiny Montgomery, up near the Canadian border at the foot of Jay Peak, holds a superlative no other town in the state can claim: with seven, it has more covered bridges than any other municipality in Vermont. Six of them were built by the same pair of local brothers, the Jewetts, in the 1800s, and finding them along the Trout River and its branches makes for a perfect slow afternoon of back-road driving. The village center is small and genuine, an old-fashioned general store and a couple of good restaurants, and Jay Peak's slopes and waterpark are minutes away. For anyone chasing the classic Vermont covered-bridge photo, this is the motherlode.
Bennington
The gem of Bennington County, this town of nearly 16,000 pairs a handsome historic downtown with a genuine literary pedigree. Grand old buildings like the Henry House and the Park-McCullough Mansion anchor the streets, and the Robert Frost Stone House Museum sits in the home where Frost lived from 1920 to 1929; his grave is a short walk away, marked with the line "I had a lover's quarrel with the world." The 306-foot Bennington Battle Monument, the tallest structure in Vermont, towers over it all.
For a quieter stretch, the One World Conservation Center protects 96 acres of meadow and wetland laced with walking trails right near town. Between the monument, the museums, and the Green Mountains rising behind it, Bennington makes a strong case as the prettiest of southern Vermont's larger towns, and a fitting place to end a tour of the state.
The Take Home
Whatever season you choose, Vermont delivers scenery that looks staged and towns that back it up. Woodstock and Montgomery trade in covered bridges, Stowe and Manchester in mountain-village polish, Bennington and Middlebury in history you can walk through. With crystal-clear lakes, sugar houses, and white steeples at nearly every turn, the hardest part is not finding a pretty town in Vermont, it is picking which one to start with.
