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This scenic, 343-mile round-trip journey begins in Burlington and delivers a winter wonderland, New England-style. Route 100, near Burlington, is your primary roadway through this frosty playground, but along the way you’ll be making detours onto some of the Green Mountain State’s prettiest country roads.
Day 1: Burlington to Stowe (36 miles)
Leaving Burlington, you’ll catch your first glimpse of Vermont’s Green Mountains driving south on Interstate 89. To your left looms the snowy peak of Mount Mansfield, Vermont’s tallest at 4,395 feet. To the right, spy the dromedary-shaped pinnacle of Camel’s Hump. It’s 26 miles to exit 10, where Route 100 winds north for 10 miles into the heart of Stowe, one of the state’s most quintessential ski towns.
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Start with an amble along Main Street through Stowe Village. Built in 1897, the Old Depot Building served as a station for the 11-mile-long Mount Mansfield Electric railway until 1932. Today it houses Bear Pond Books, the second-largest independent bookseller in Vermont, and Stowe Mercantile, which stocks a cornucopia of country store curios, including an impressive selection of Vermont maple products. Around the corner on Pond Street, The Current, a center for contemporary art, displays thoughtfully curated exhibitions of both well-known and emerging artists. Back on Main Street, pair a locally crafted beer, cider or mead with a Vermont cheese plate at the Stowe Public House & Bottle Shop. Cap off the day with Umiak Outdoor Outfitters’ guided moonlight fondue tour: You'll snowshoe along wooded trails to the Stowehof Hotel’s Fritz Bar for a three-course dinner with fondue.
Where to stay: The Green Mountain Inn, which has been hosting visitors to Stowe since 1833, features 104 antique-filled guest rooms, suites and apartments.
Day 2: Stowe to Waitsfield (46 miles)
Kick off the morning with house-made biscuits, eggs Benedict and challah French toast at Butlers Pantry on Stowe's Main Street. Fully fueled, head south on Route 100 for 10 miles to U.S Route 2 West. From there it’s a 15-minute drive to Bolton Valley, a family-owned ski resort packed with charm. Ski its gentle, evergreen-lined slopes or its more challenging glades — or hit its 62 miles of cross-country and snowshoe terrain. A favorite: The mile-and-a-half loop up Bryant Trail and down Gardiner’s Lane, a heart-pumping trek through winter scenery. Après-adventure, warm up by the fire at James Moore Tavern at the main base lodge; order the Bolton Smash Burger and a pint of Burlington-brewed Switchback Ale.
Return to Route 100 and continue south for 25 miles to the Mad River Valley. Bookended by the twin villages of Waitsfield and Warren, this bucolic valley is home to two ski areas, quaint main streets and a smattering of covered bridges. One of those, the Waitsfield Covered Bridge, stretches across the Mad River in the center of town and begs for a quick stroll. When you get to Waitsfield's town center, grab a coffee and a baked treat — don’t miss the maple walnut cookies! — at the Sweet Shop. Next door, browse the work of more than 150 Vermont artists and makers in the Artisans’ Gallery. If it’s a weekend (or you make an appointment), explore the Madsonian Museum of Industrial Design, featuring pieces curated by local architect Dave Sellers. Come evening, dine six miles south in Warren on splurge-worthy fare at The Pitcher Inn, where Chef Jacob Ennis prepares slow-cooked meats and roasted root vegetables over a 19th-century-style hearth.