Visiting Wilmington, Vermont? What to See, Do and Eat on Your Trip

Wilmington sits at the intersection of Routes 9 and 100, two of Vermont’s most scenic drives. No matter which way you get there, the tiny village in the Deerfield Valley makes the most of its surroundings, from an expansive man-made lake to nearby ski resorts. Much of the formerly industrial town is now part of the Wilmington Village Historic District, which is listed on the National Register of Historic Places. Stop into its 19th-century buildings to shop for antiques, grab a bite or browse a local art show — if you’re not too busy exploring the outdoors, that is.

If you want to visit Wilmington, Vermont, here’s a suggested itinerary.

Note: Check websites to confirm business hours for the day you visit.

Dot’s Restaurant

Any trip to Wilmington should start at Dot’s Restaurant, an institution so beloved that the town banded together to fund its renovation and reopening after Tropical Storm Irene destroyed it in 2011. The laid-back spot opens at 6 a.m. with diner fare such as berry-berry pancakes, sausage gravy and biscuits, and the McDot breakfast sandwich. For lunch, don’t miss the chili — especially after a chilly morning on the slopes.

3 W. Main St., Wilmington

View Local Art

Usually, if your GPS tells you something’s not a road, you should listen. But up Wilmington’s Not A Road, you’ll find Skip Morrow’s the Art of Humor Gallery (30 Not A Rd.), a two-story space dedicated to the cartoonist’s self-described “notoriously bizarre originals and prints for the eclectic collector.” Back in town, on less obscurely named streets, art lovers can stroll through exhibits — and take a class — in a former church at Arthouse Studio, Gallery & Lounge (12 S. Main St.) or view local landscape paintings at Jim McGrath Gallery (22B W. Main St.). If you time your visit for late July or early August, the annual Deerfield Valley Blueberry Festival brings a berry good lineup of artisans and events to the area, from concerts to craft fairs to pancake breakfasts.

Harriman Reservoir

Also called Lake Whitingham, this pristine man-made body of water is the largest entirely within Vermont’s borders. Cruise its eight-plus-mile length by boat or kayak, stop to fish, or jump in for a swim at Wards Cove, Castle Hill picnic area or Mountain Mills. No boat of your own? Rent one from High Country Marine (403 Route 9). Walkers — and cross-country skiers, in winter — can wind along the lake via an old rail trail, now part of the state’s 300-mile-long Catamount Trail ski system. And if you’re into unfortunately monikered hydroelectric infrastructure, gaze at the Glory Hole — an expansive concrete funnel spillway that’s actually named for its resemblance to a morning glory flower — near the southern end, on Dam Road.

Valley Craft Ales

Up the Deerfield River from the reservoir, this brewery’s deck is the place to be in the summertime, when live music spills out over the stream below. But that’s just one of the offerings at this brewery, pizza place and inn, which is cozy in the winter, too. The rooms are utilitarian, but the pizza and beer are standouts no matter the season. Pair a bacon-topped New Haven-style pie with a For Wilmington, With Love IPA, or a garlicky white pie with an old-school Foxon Park soda. If you’re looking for another buzz, brewery co-owners Brian and Chrystal Holt also own nearby 1a Coffee Roasters (123 W. Main St.), a solar-powered café that serves perfect flat whites and iced coffee in reusable glass jars.
18 N. Main St., Wilmington

Ski and Bike Mount Snow

Skiing might be the most common reason first-timers end up in Vermont. Just over 20 miles from the Massachusetts border — and 8.5 miles from Wilmington — Mount Snow is the first mountain most folks hit on their drive north. The Vail-owned resort has four faces, with 85 trails, 19 lifts and 100 acres of terrain parks. In the summer, the lifts turn over to mountain bikers for a different sort of downhill thrill.
39 Mount Snow Rd., West Dover

Wilmington Antique & Flea Market

From mid-May through mid-October, southern Vermont’s largest weekend market takes over a 10-acre field roughly a mile east of town. The family-owned market, which started in 1983, offers a self-described “potpourri of antiques” and other goods, from vintage botanical prints and records to jewelry and wooden snowshoes. It’s free to park and enter, and food is available for purchase.
225 Route 9, Wilmington

Molly Stark State Park

General John Stark led his troops to victory at the Battle of Bennington in 1777, but it’s his wife, Molly, whose name graces a state park and scenic byway in southern Vermont. Molly “didn’t bow to her husband’s demands,” according to a history written by the Vermont State Parks. She did help him out, though, by recruiting militiamen and opening a makeshift hospital in her barn — both of which made her “instrumental to the American success at the Battle of Bennington,” the Parks’ history says. Molly’s namesake park offers ample campsites and facilities, a play area, a rentable pavilion, and a hiking trail that leads to the Mount Olga fire tower, offering vast views.
705 Route 9, Wilmington