A Summer Drive Along Vermont’s Main Street

A vacation with all the Americana charms of Norman Rockwell and apple pie.

By Gina DeCaprio Vercesi

Vermont Route 100, also known as Vermont’s Main Street or the Skiers’ Highway, is one of the most scenic drives in New England—and the United States, for that matter. Winding north from the Massachusetts border, the 216-mile roadway leads travelers through a quaint landscape of green valleys and pretty villages and is home to a slew of diversions to fill a long-weekend summer road trip.

Wilmington and Dover

Set along the Deerfield River, tiny Wilmington makes for a convenient stop about a half hour into your journey. Just outside of town is Hogback Mountain, where summit views extend for 100 miles across mountains and into three states. You can hike the mountain before heading into Wilmington.

When you reach the town, consider popping into The Art of Humor Gallery (30 Not-a-Road, Wilmington; 802-464-5523; admission, $5, which can be applied to any purchase). Here, famed cartoonist Skip Morrow showcases his oddball doodles and sometimes puts on digital drawing demonstrations. Come lunchtime, Dot’s Restaurant (3 Main St., Wilmington; 802-464-7284; lunch for two, $12*) is a local institution. Hurricane Irene nearly destroyed the diner in 2011, but a host of loyal patrons helped bring it back to life. Down the street at The Vermont Bowl Company (11 Main St., Wilmington; 802-464-5296), John McLeod has been handcrafting heirloom-quality home wares since 1967, and not just bowls—you’ll also find serving platters, lazy Susans, cutting boards, and more.

After lunch, it’s about a seven-mile drive north to Dover, where you can hit the slopes on two wheels with a downhill-mountain-biking clinic at Mount Snow (West Dover; 802-464-2151; two-hour packages, $109). Newbies can try their luck on Gateway, the longest beginner downhill trail in the East.

Warren and Waitsfield

Back on the road, it’s about another two and a half hours to the sister villages of Warren and Waitsfield, which anchor the Mad River Valley. Waterfalls, rustic barns, and a trio of covered bridges pepper the area.

You can start by making a pit stop at The Warren Store (284 Main St., Warren; 802-496-3864) for everything from penny candy and hand-knits to specialty sandwiches and local brews. From here, it’s only a few miles farther north to Waitsfield. The whole family can dive into old-fashioned fun at the Lareau Swim Hole (Waitsfield), which offers both shallow and deep waters, the latter surrounding a giant glacial boulder near the center of the swimming hole. Before you take a dip, consider putting your name in across the way at American Flatbread (46 Lareau Rd., Waitsfield; 802-496-8856; dinner for two, $24). The wood-fired-pizza joint often draws a crowd, so it pays to think ahead.

Or, if you’re traveling without kids, you might prefer an afternoon at The Bundy Modern (361 Bundy Rd., Warren; 802-583-5832; admission, free), a contemporary gallery housed in a restored Bauhaus-style gem. Afterward you can tuck into rustic flavors at Peasant (40 Bridge St., Waitsfield; 802-496-6856; dinner for two, $50), a Tuscan-inspired kitchen helmed by a husband-and-wife team.

Waterbury and Stowe

Travelers have long flocked to the Ben & Jerry’s Factory Tour (1281 Waterbury–Stowe Rd., Waterbury; 802-882-2047; 30-minute guided factory tours, $4 a person; children 12 and under, free), in Waterbury, about a 15-mile drive from Waitsfield. Tours run every half hour and share the story of how two friends launched the Vermont-based ice cream brand and then end with a sample scoop.

In nearby Stowe, thrill seekers soar down Mount Mansfield, Vermont’s highest peak, on the 4,462-foot long ZipTour Adventure (802-253-3685; two-hour zipline tours, $135 a person). You can hunt for keepsakes among a trove of made-in-America goods—such as waxed-canvas handbags or vegan skin-care products—at Tangerine & Olive (232 Mountain Rd., Stowe; 802-760-6692). The boutique showcases products handcrafted or manufactured in small batches by independent designers.

You can take a short detour on Vermont Route 108 through Smugglers’ Notch State Park (6443 Mountain Rd., Stowe; 802-253-4014). The park’s namesake pass, which once served as a smugglers’ route to and from Canada, bends through the forest between Mount Mansfield and Sterling Mountain. Along the way, you can hop off and hike Sterling Pond Trail; the trailhead is across from the Smugglers’ Notch Visitor Center on Route 108.

Johnson and Jeffersonville

If you’d rather explore on water than on land, pick up a paddle and hit the Lamoille River with Vermont Canoe & Kayak (4805 Rte. 14, Jeffersonville; 802-644-8336; three-hour Water and Wine tours, $60 a person), in Jeffersonville. The Water and Wine package starts with a 90-minute paddle trip to Boyden Valley Winery (63 Rte. 104, Cambridge; 802-644-8151), where you’ll disembark for a private tour and wine tasting.

In Johnson, about a 15-minute drive east of Jeffersonville, the cozy plaids at Johnson Woolen Mills (61 Lower Main St. E., Johnson; 877-635-9665) will have you yearning for cooler temperatures. The mill’s coats, throws, and mittens have been keeping Vermonters warm since 1842. Then you can head back west to kick off happy hour at Smugglers’ Notch Distillery (276 Main St., Jeffersonville; 802-309-3077; tasting flights, $8). The father-son producer just released a gluten-free vodka, a new addition to its menu of gins, whiskeys, rums, and bourbons. Evening should find you perusing the extensive menu at 158 Main (158 Main St., Jeffersonville; 802-644-8100; dinner for two, $50). The restaurant, which serves everything from pan-seared New England scallops to a traditional Vermont turkey dinner, holds court as the most popular place in town.

  • *Estimated meal prices do not include drinks, tax, or tip.
  • NOTE: Information may have changed since publication. Please confirm key details before planning your trip.
  • Published: July 2018