Vermont Route 100: The quintessential New England road trip

Often called the “Skiers’ Highway” to honor the alpine giants that elevate its path, Vermont Route 100 is one of New England’s most scenic drives. Winding right through the middle of Vermont from Wilmington in the south to Newport in the north, the route traces the eastern edge of the Green Mountain National Forest as it travels amid a landscape of verdant river valleys, quaint towns, and bucolic pastures.

While Vermont Route 100 is a favorite road trip for leaf peepers, summer reveals its own brand of magic. The scenic road offers a slew of diversions perfect for long, warm days—hiking trails, swimming holes, craft breweries, farm stands, and mom-and-pop–style general stores selling everything from flannel shirts and firewood to house-made cider doughnuts and Vermont’s famous creemees, or soft-serve ice cream.

So cue up the Phish playlist and use these suggestions to hit the road for a few days (or longer if you have the time). Remember: The best road trips are about the journey, not the destination.

Vermont Route 100 finds its groove west of Brattleboro in Wilmington, a snug village set alongside the Deerfield River. In 2011, Hurricane Irene’s floodwaters knocked many of the town’s historic buildings clean off their foundations, but this tight-knit community has made its way back onto solid ground. Right outside of town, the Southern Vermont Natural History Museum is home to more than 600 mounted specimens of native birds and mammals. Live-animal exhibits feature two bald eagles, several owls, a pair of orphaned baby possums, and Remi, a raven whose intelligence is often touted on the museum’s Instagram account. Nearby, Vermont Distillers produces an array of craft liqueurs and spirits, which you can sip on the deck overlooking Hogback Mountain—its flagship Maple Cream Liqueur is pure Vermont in a bottle.

Downtown Wilmington’s well-preserved 18th- and 19th-century architecture helped secure its spot on the National Register of Historic Places. Tucked into the elbow of the town’s only intersection (with Route 9, the Molly Stark Highway), Dot’s Restaurant has served comforting classics such as honey fried chicken and meat loaf with gravy and mashed potatoes that have made it a favorite of locals and visitors alike for more than 40 years. Work off the calories with a stroll along West Main Street. Find your next great read in Bartleby’s Books, where owner Lisa Sullivan features gifts, games, cards, and books of every genre. Upstairs, a tiny gallery showcases the work of local painter Ann Coleman. Down the block, Scottish native John McLeod has been designing and handcrafting heirloom-quality wooden bowls, cutting boards, and serving pieces at the Vermont Bowl Company since 1967.

Back on Route 100, head north toward the hamlet of Dover. If you’re feeling adventurous, hit the slopes on two wheels with a downhill mountain biking clinic at Mount Snow—newbies will love Gateway, the longest beginner trail in the east. On the way back to town, grab a beer at the Dover Bar and Grill, a semi-reformed dive bar known affectionately to locals as “DBag.” Famous for its artery-clogging smash burgers and vintage ski-hill memorabilia, DBag’s backyard hang feels like being at a friend’s cookout. Be sure to try your hand at ax throwing. It’s addictive.

Stay: Built in 1894 and tucked along West Main Street, the historic Wilmington Inn makes an ideal home base. Innkeepers Megan and Charlie Foster have lovingly renovated the entire property, and some of the 10 individually decorated rooms have gas fireplaces and cozy seating areas. In the evenings, chat with Charlie at the bar or settle into one of the bright-red Adirondack chairs around the outdoor fire. Megan’s hearty breakfasts include fluffy pancakes and frittatas made with eggs from the inn’s own chickens.

From Wilmington, it’s a meandering, three-hour drive to Waitsfield and the Mad River Valley. On the way north, several spots merit a closer look. Rawsonville, 30 miles north of Wilmington, is a tiny enclave with a gas station, a coffee shop, a sports store, and Meulemans’ Craft Draughts—a trove of fermented goodness with local and regional beers, ciders, meads, and wines. Across the way, step into Honeypie, a classic roadside eatery housed in an old gas station that turns fresh, locally sourced ingredients into elevated diner fare.

History buffs will enjoy the short detour on Vermont Route 100A to the Calvin Coolidge State Historic Site in Plymouth Notch, an early 20th-century village tucked into the Green Mountains and one of the country’s best-preserved presidential homesteads. The site includes Coolidge’s birthplace and boyhood home, a general store, a one-room schoolhouse, and the 1924 Summer White House. From there, it’s about an hour to Granville Gulf Reservation State Park, where a short hike leads to the base of Moss Glen Falls, a spectacular 80-foot cascade.

The Mad River Valley could be its own Vermont highlight reel with charming villages, rustic barns, covered bridges, and breathtaking mountain vistas. Get acclimated with a walk along Main Street in Waitsfield. At the Mad River Glass Gallery, husband-and-wife team David and Melanie Leppla create blown and cast bowls, vases, lanterns, and cairns. Browse hand-thrown stoneware made by master potter Ulrike Tessmer at Waitsfield Pottery. Around the corner on Bridge Street, a 19th-century general store houses Artisans’ Gallery, home to a selection of beautifully curated, made-in-Vermont pieces that include everything from wood furniture to ceramics, fiberware, jewelry, paintings, photography, and sculpture.

You’ll find the quintessential Vermont swimming hole on the south side of town at the Lareau Park, where a sandy beach, a wide grassy lawn, and giant boulders for jumping make it a favorite spot for locals and visitors alike. If the dinner hour beckons, consider putting your name in across the way at American Flatbread—the wood-fired pizza joint tends to draw a crowd. Or tuck into rustic flavors on the north side at Peasant, an inviting, Tuscan-inspired restaurant with a seasonal menu helmed by Valley locals Chris and Mary Ellen Alberti.

If dinner with a view is more your style, gather provisions a few miles south at the Warren Store. This “Almost World Famous” mercantile sells fresh-baked bread, made-to-order sandwiches, from-scratch baked goods, and plenty of local goodies. From there, it’s a 10-minute drive up the Lincoln Gap Road to the Sunset Ledge trailhead. Follow the trail for about a mile to the ledge, which, as its name suggests, faces west. Spread out your picnic and watch as the summer sun dips into the wide Champlain Valley.

Stay: Once a Civilian Conservation Corps bunkhouse, the Mad River Barn a few miles west of Waitsfield has been a Valley fixture since the 1930s. Today, 18 inviting rooms decorated in a chic, rustic style are spread throughout three buildings—the Barn, the Farmhouse, and the Longhouse—and sleep up to six guests in multiple configurations. The on-site bar features an impressive array of locally distilled craft spirits and brews while the pub menu showcases the best of Vermont’s growers and producers.

As the road climbs out of the Mad River Valley and enters Waterbury, a trifecta of attractions—Ben and Jerry’s, the Cabot Store, and the Cold Hollow Cider Mill—tempts travelers every mile or so just north of Interstate 89. If you’ve got kids in tow (and even if you don’t), resisting the siren song of Vermont’s legendary ice cream duo is tough. The flagship factory, which produces approximately 350,000 pints a day, offers tours throughout the day, and the on-site Scoop Shop serves up the iconic flavors in cones, sundaes, and milkshakes.

In Stowe, start by exploring the town’s quaint Main Street, punctuated on one end by Stowe Community Church and on the other by the circa-1818 Town Meeting House. The latter houses the Vermont Ski and Snowboard Museum, which focuses on the state’s storied winter sports heritage. Down the street at Stowe Mercantile, its jars of penny candy; kitschy, Vermont-inspired ephemera; and bright-red vintage Stowe Mountain gondola will take you back in time.

From Route 100, it’s about 8 miles on Vermont Route 108—better known as the Mountain Road—to Stowe Mountain Resort and Mount Mansfield, the state’s highest peak. To reach the summit ridge, take the historic Auto Toll Road, which switchbacks up the mountain to a parking area at 3,850 feet. From there it’s a short—but somewhat harrowing—ridgeline hike along a stretch of Vermont’s iconic Long Trail to the 4,393-foot summit of Mount Mansfield, also known as the “Chin.” Another option is to take a scenic ride on the Stowe Gondola to the Cliff House, where you can enjoy lunch with panoramic views of the surrounding alpine peaks.

For adventures without an elevation gain, you can rent bikes at Mountain Ops Outdoor Gear at Topnotch Resort to pedal the Stowe Recreation Path. The flat, picturesque path begins right outside the shop door and winds for 5.5 miles back to town, crisscrossing the West Branch of the Little River at several points along the way. Because the trail runs parallel to the Mountain Road, cyclists have lots of options for pit stops. On Sundays, the Stowe Farmers’ Market sets up about halfway down the trail and features live music, friendly vendors, and a bounty of goodies grown, made, and produced in Vermont.

Stay: Set back from the bustle of the Mountain Road but close to all of Stowe’s offerings, Topnotch Resort features 68 stylish rooms with mountain views, two restaurants with seasonally inspired menus, and an expansive outdoor area with fire pits, a bocce court, and plenty of comfortable seating. Outdoor adventures abound, and guests can hike, ride horses, and play tennis right on the property. But perhaps the best part is the resort’s lavish spa, with Vermont-themed treatments like the Total Hops Massage and the Maple Sugar Body Smoothie.

Gina DeCaprio Vercesi is a New York–based writer with a passion for history and conservation—and 1973 Buick Skylark convertibles.