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Route overview
This seven-day road trip traces the spine of the Green Mountains. By combining Route 100 — Vermont’s Main Street, running north to south through the center of the state — with Route 7 in the western valley and Route 9 over the southern mountain pass, you cover 380 miles of historic villages, covered bridges, mountain passes and local food stops.
The loop runs Burlington to Stowe, south through Waterbury and the Mad River Valley, on to Woodstock and Quechee, down through Ludlow and Weston to Brattleboro, west to Bennington and north up Route 7 through Manchester and Middlebury, back to Lake Champlain.
Day 1: Burlington to Stowe via Waterbury
Forty-five miles, about an hour and ten minutes. Depart Burlington early on I-89, exit onto Route 2 toward Waterbury and turn north onto Route 100.
Three stops make the drive. The Ben & Jerry’s factory in Waterbury offers a guided tour, the history of Vermont’s most famous dairy brand and a scoop shop. Cold Hollow Cider Mill in Waterbury Center runs a traditional rack-and-cloth press — do not leave without a dozen hot cider donuts. The Cabot Farmers' Store, in the same complex, pours tastings of aged cheddars, jams and Vermont wines.
Arrive in Stowe, often called the ski capital of the East, and walk the Stowe Recreation Path, a 5.3-mile paved greenway crossing wooden bridges over the Little River. Late afternoon, visit The Alchemist on Cottage Club Road to sample Heady Topper, the double IPA that launched the New England IPA style.
Day 2: Smugglers' Notch & Mount Mansfield
Thirty miles as a loop, about an hour of driving, and a full day on the mountain.
Morning: drive north on Route 108 through Smugglers' Notch, a narrow pass with 1,000-foot vertical cliffs where the road drops to a single lane as it weaves around glacial boulders. Midday: park at the top of the pass and hike the Sterling Pond Trail, 2.8 miles round trip and steep, to a high-altitude pond with trout fishing and quiet vistas.
Afternoon: drive the Mount Mansfield Auto Toll Road, 4.5 miles of unpaved mountain road, up to 3,850 feet, then walk the ridge trail toward the Chin — Vermont’s highest point at 4,393 feet. Evening: dine at Doc Ponds for elevated comfort food and a massive vinyl collection, or at the von Trapp Brewery and Bierhall for Austrian lagers and fondue.
Day 3: the Mad River Valley
Fifty miles, about an hour and a half. Head south on Route 100 into the Mad River Valley, a region that has preserved its rural Vermont character without big-box stores or high-rise resorts.
Drive past Mad River Glen and Sugarbush, the historic ski areas that define New England skiing culture. Stop at the Warren Store, an 1870 country store sitting directly over the Mad River — order a custom deli sandwich and eat it on the deck above the rushing water. The Warren Covered Bridge, just off Route 100, is a timber-truss span over a popular summer swimming hole. Finish at Lawson’s Finest Liquids in Waitsfield for Sip of Sunshine and small-batch taproom exclusives.
Day 4: Woodstock, Quechee Gorge & Plymouth Notch
Sixty-five miles, about an hour and forty-five minutes. Continue south on Route 100, then turn east toward Woodstock, widely considered one of the most picturesque small towns in America.
At Plymouth Notch, the President Calvin Coolidge State Historic Site preserves the 1920s village where the 30th president was born and took the oath of office by kerosene lamp; try the raw-milk cheddar at the Plymouth Cheese Factory on site. In Woodstock, Billings Farm & Museum is a working Jersey dairy farm and museum of Vermont’s rural heritage. Quechee Gorge, called Vermont’s little Grand Canyon, is a 165-foot-deep chasm carved by glacial activity — view it from the Route 4 bridge or hike down to the river trail.
Day 5: southern Route 100 to Brattleboro
Seventy-five miles, about two hours, south through the central Green Mountains via Ludlow, Weston and Wilmington.
The Vermont Country Store in Weston is a sprawling, world-famous emporium of retro toys, cheddar wheels, oil lamps, maple candies and traditional New England goods. Hogback Mountain Overlook on Route 9 between Wilmington and Brattleboro offers the famous hundred-mile view south over Vermont, Massachusetts and New Hampshire.
Arrive in Brattleboro, Vermont’s southeastern corner, with its arts scene, historic brick storefronts along the Connecticut River and independent bookshops. Dinner at TJ Buckley’s, a restored 1920s diner serving upscale local cuisine, or Whetstone Beer Co. overlooking the river.
Day 6: Bennington & Manchester up Route 7
Sixty miles, about an hour and twenty-five minutes. Turn west on Route 9 over the southern pass, then head north on Route 7.
In Bennington, the Bennington Battle Monument is a 306-foot stone obelisk commemorating the 1777 Revolutionary War battle; the elevator to the top gives views of three states. Drive through Old Bennington for colonial homes and three covered bridges over the Walloomsac River — Silk Road, Paper Mill and Henry.
North in Manchester, nestled between the Taconic and Green Mountains, Hildene is the 412-acre estate of Robert Todd Lincoln, with a 1905 Georgian Revival mansion, formal gardens, a Pullman car and a working goat dairy. The Equinox Mountain Skyline Drive climbs 5.2 miles of toll road to 3,848 feet.
Day 7: Middlebury, Vergennes & back to Burlington
Fifty-five miles, about an hour and fifteen minutes, north along the western valley through historic college towns and rolling agricultural countryside.
Middlebury, home to Middlebury College, has a historic town green, a covered bridge over Otter Creek Falls and the Middlebury College Museum of Art. Stop at Shelburne Vineyard or Lincoln Peak Vineyard to taste cold-hardy hybrids like Marquette and La Crescent. Then complete the 380-mile circuit back at Lake Champlain.
Seven-day summary
Route, highlights and where to sleep each night.
Day 1 — I-89 east to Route 100 north: Waterbury, Ben & Jerry’s, Stowe Rec Path. Sleep in Stowe.
Day 2 — Route 108 and the Notch: Smugglers' Notch, the Mansfield ridge, breweries. Sleep in Stowe.
Day 3 — Route 100 south: Mad River Valley, Warren Covered Bridge. Sleep in Warren or Waitsfield.
Day 4 — Route 100 south to Route 4 east: Plymouth Notch, Woodstock, Quechee Gorge. Sleep in Woodstock.
Day 5 — Route 100 south to Route 9 east: Vermont Country Store, Hogback Overlook, Brattleboro. Sleep in Brattleboro.
Day 6 — Route 9 west to Route 7 north: Bennington Monument, Hildene. Sleep in Manchester.
Day 7 — Route 7 north: Middlebury, valley vineyards, Burlington.
Good to know
What is the best Vermont road trip route?+
Route 100 north to south down the center of the state, combined with Route 9 over the southern pass and Route 7 back up the western valley — a 380-mile loop from Burlington to Brattleboro to Bennington and home.
How many days do you need to drive Vermont?+
Seven is ideal for the full loop: two nights in Stowe, one each in the Mad River Valley, Woodstock, Brattleboro and Manchester, returning to Burlington on day seven. Five days works if you skip Bennington and Manchester.
What is Route 100 known for?+
It is called Vermont’s Main Street and the Skier’s Highway. Running 216 miles through the center of the Green Mountains, it links nearly every ski area in the state and passes covered bridges, cider mills, country stores and roadside waterfalls.
Is Smugglers' Notch worth driving?+
Yes, in season. Route 108 through the Notch is a narrow pass beneath 1,000-foot cliffs where the road narrows to one lane around glacial boulders. It closes in winter, and RVs and trailers cannot make the turns.
What should I not miss on a week in Vermont?+
Cold Hollow’s cider donuts, The Alchemist in Stowe, the ridge of Mount Mansfield, the Warren Store and Covered Bridge, Quechee Gorge, the Vermont Country Store in Weston, and Hildene in Manchester.