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.
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.
Where to stay: In Waitsfield, settle into one of a dozen inviting rooms at the Inn at Round Barn Farm, set on 245 acres with five ponds and one of Vermont’s last remaining round barns.
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Day 3: Waitsfield to Woodstock (60 miles)
After breakfast, head back to Warren for more winter fun in the outdoors. Make your first stop The Warren Store, an eclectic country market that sells everything from Vermont-made pottery to handcrafted soaps, local beer and tasty sandwiches — order the No. 6 (roast turkey with house-made cranberry mayonnaise) for a trailside picnic lunch later in the day. Then, head to Blueberry Lake Cross Country Center, a local favorite for 41 years nestled into the forest two miles east of Warren on Plunkton Road. Rent fat bikes — low-pressure tires make pedaling on the snow a breeze — and take a spin through the woods on one of the center’s 20 miles of trails for all levels of riders, even beginners.
Continue on Route 100, which twists through a dense, five-mile swath of forest before opening back up into farmland where the snug hamlets of Granville, Hancock and Rochester dot the rural landscape. At Green Mountain Glassworks in Granville, artist Michael Egan creates whimsical, hand-blown glassware and sculptures. Farther south, the Rochester Cafe & Country Store hawks homey ephemera as well as salted caramel hot cocoa in the adjacent café. Eight miles from Rochester, take Vermont Route 107 East another eight miles, then turn onto Vermont Route 12 South, which leads into Woodstock, one of Vermont’s prettiest towns.
All along Elm and Central streets in Woodstock Village, 19th-century brick buildings house village mainstays such as F.H. Gillingham & Sons general store and The Vermont Flannel Company. Central Street ends at the Green, Woodstock’s community front yard. On one side, the Middle Covered Bridge — a 139-foot-long lattice truss structure — spans the Ottauquechee River. On the other, the elegant, federalist-style Woodstock Inn and Resort stands sentinel. For dinner, relax in the Inn's Red Rooster bar to dine on warming fare such as Heirloom Squash Soup and a juicy burger, or go for tapas at the downtown Melaza Bistro.
Where to stay: The Woodstocker B&B has nine rustic-chic rooms with king beds; two spacious suites have infrared saunas. It's within walking distance of downtown restaurants like Melaza.
Day 4: Woodstock to Grafton (54 miles)
Delve into a 150-year legacy of sustainable land stewardship at the 500-acre Marsh-Billings-Rockefeller National Historic Park, named for three generations of conservation-minded residents. Explore the winter landscape with a mellow hike along the park’s main carriage roads, or rent gear and purchase trail passes at the Woodstock Inn’s Nordic Center for some snowshoeing or Nordic skiing. On winter weekends (closed weekdays), check out the Billings Farm & Museum, where you’ll find livestock barns, the 1890 Farm Manager House and exhibits.
Now, drive five miles west on U.S. Route 4 for lunch at Mountain Creamery, where farmers Boris and Sheila Pilsmaker serve hearty soups and sandwiches made with hyper-local ingredients, many from their own farm. En route, browse the simple-yet-stunning stoneware in Farmhouse Pottery’s flagship store and make a quick stop at the circa-1877 Lincoln Covered Bridge, whose design inspired the steel highway and railroad bridges of today.
After lunch, continue on Route 4 for nine miles to reconnect with Route 100. A 45-minute drive south leads to Weston and The Vermont Country Store, a place many folks recognize for its nostalgia-packed catalogs. You could easily while away an hour perusing the “practical and hard-to-find” items the Orton Family has sold since 1946 — from wool sweaters and sheepskin slippers to penny candy and percolators. Just past the store, turn left onto the Weston-Andover Road for 12 miles, then follow Vermont Route 35 for seven miles through rolling countryside to Grafton, a beautifully preserved, 19th-century mill town.
Where to stay: Period furnishings and classic New England décor give the 45-room Grafton Inn special appeal. A former stagecoach stop, the inn dates back to 1801.
Day 5: Grafton to Burlington (142 miles)
Spend an hour or two exploring Grafton’s picturesque village. On Main Street, don’t miss the Turner Hill Interpretive Center, which tells the story of an escaped slave who fought in the Civil War and later raised his family in Grafton; the gallery of sculptor Jud Hartmann, whose detailed bronze figures depict the Northeastern Native Americans; and MKT: Grafton for Vermont-made gifts and groceries, including a selection from the Grafton Village Cheese Co.
Hop onto Route 35 and backtrack north for seven miles to Chester, then head east on Vermont Route 103 for nine miles to Interstate 91 North. From there it’s a little more than two hours on I-91 and I-89 to Burlington.
At the Church Street Marketplace, Burlington’s pedestrian-friendly downtown hub, peruse new and used reads at Crowe Bookshop, invest in cozy new togs at Outdoor Gear Exchange, pick up a box of luscious Lake Champlain Chocolates, and shop for Vermont-made jewelry and crafts at Frog Hollow craft gallery. Come dinnertime, dine at Juniper at Hotel Vermont for seasonal fare, such as Spiced Brisket Poutine. Start with cocktails by the outdoor fire pit — the Old Fashioned, made with rye whiskey from WhistlePig's distillery near Woodstock, takes the classic to new heights.
Where to stay: At the rustic-chic Hotel Vermont, 125 airy rooms treat guests to plush beds, cozy Vermont flannel robes and local bath products.
Winter Driving Tips
Gina DeCaprio Vercesi is a New York-based journalist with a passion for outdoor adventure. She contributes to National Geographic Traveler and Travel + Leisure.