Vermont and New Hampshire share one of the country’s classic fall drives — a loop from Boston through Woodstock’s covered bridges and a working dairy farm, over to Stowe for cider donuts and a gondola ride above Mount Mansfield’s color, then home across the Kancamagus Highway’s forty-four unbroken miles of White Mountains overlooks. Real inns, real drive times, and 2026 prices for every stop.
Day 1Boston to Woodstock: Covered Bridges & a Working Dairy Farm
The loop starts at Boston Logan and heads north into Vermont, with a stop at the state’s best-known gorge before settling into Woodstock’s village green for the night.
🚗 Self-Drive — Boston Logan Airport to Woodstock, VT
~2.5 hours · rental car required for the loop
Boston Logan International Airport (BOS) is the easiest gateway for this loop, about two and a half hours from Woodstock on I-93 and I-89 — a rental car is essential, since the drive between towns is the whole point of the trip.
Hertz — Boston Logan Airport · +1 800 654 3131 · www.hertz.com/us/en/location/unitedstates/massachusetts/boston/bost11
🌉 Quechee Gorge
~30–45 minutes · Free
Vermont’s “Little Grand Canyon” — a 165-foot-deep gorge carved by the Ottauquechee River, spanned by a steel bridge on Route 4 with a short path down to the water and one of the state’s most-photographed fall overlooks.
🐄 Billings Farm & Museum
~1.5–2 hours · $20 adult / $18 senior / $10 child (5–15)
A working dairy farm founded in 1871, with Jersey cows, draft horses, and farmhouse exhibits set against Mount Tom — one of the best-preserved 19th-century farms in New England, a short walk from Woodstock’s village green.
Billings Farm & Museum · +1 802 457 2355 · billingsfarm.org
🍽️ Dinner — Simon Pearce Restaurant, Quechee
~1.5 hours · Est. $40–55 USD / person
New American cooking on a deck cantilevered over the Ottauquechee River’s waterfall, next door to the Simon Pearce glassblowing studio — order the cider-braised pork or the trout, plated on glassware made downstairs.
Simon Pearce Restaurant · +1 802 295 1470 · simonpearce.com
🛎️ Overnight — Woodstock Inn & Resort
From $329–459 USD / night, for 2 people
A grand fieldstone-fireplace inn on Woodstock’s village green, walking distance to covered bridges and the shops on Elm Street — golf, a spa, and some of the best people-watching in Vermont during peak leaf season.
Woodstock Inn & Resort · +1 802 457 1100 · www.woodstockinn.com
Day 2Woodstock to Stowe: Cider Donuts & a Gondola Above the Color
The drive north crosses into ski country, with a stop for Vermont’s best-known cider donuts before riding a gondola above Mount Mansfield’s fall color.
🚗 Self-Drive — Woodstock to Stowe
~1.25 hours · via Route 100
Route 100 runs north through Vermont’s dairy country and the ski towns of the Mad River Valley before climbing into Stowe — one of the prettiest stretches of two-lane road in the state, especially with the maples turning.
🍩 Cold Hollow Cider Mill
~30–45 minutes · cider & donuts priced by item
A working cider mill in Waterbury Center pressing apples the old-fashioned way since 1974, with hot cider donuts made all day and a viewing window onto the press — the classic first stop on any Stowe-bound drive.
Cold Hollow Cider Mill · +1 802 244 8771 · coldhollow.com
🚡 Gondola SkyRide — Stowe Mountain Resort
~1.5–2 hours · Est. $46 USD / adult round trip
An eight-passenger gondola climbs to 3,625 feet on Mount Mansfield, Vermont’s highest peak, for a ridge-top view over the Green Mountains’ fall color — on a clear day the White Mountains are visible on the horizon to the east.
Stowe Mountain Resort · +1 802 253 3000 · www.stowe.com
🍽️ Dinner — von Trapp Brewing Bierhall
~1.5 hours · Est. $25–35 USD / person
A Bavarian-style beer hall on the von Trapp family’s own alpine lodge grounds, pouring Austrian-style lagers brewed on-site alongside schnitzel and pretzels — long communal tables and a mountain view that explains the family’s choice of Vermont.
von Trapp Brewing Bierhall · +1 802 253 5750 · www.vontrappbrewing.com
🛎️ Overnight — Topnotch Resort, Stowe
From $299–379 USD / night, for 2 people
A ski-country resort on Mountain Road with mountain views from many rooms, a well-regarded spa, and a short drive to both the gondola and Stowe’s restaurants — a comfortable base for the second night of the loop.
Topnotch Resort · +1 802 253 8585 · www.topnotchresort.com
Day 3Smugglers’ Notch to the Kancamagus Highway
The last day threads a narrow mountain pass out of Vermont before joining New Hampshire’s best-known scenic byway for the drive back to Boston.
🚗 Self-Drive — Smugglers’ Notch to North Conway
~2 hours · Route 108, then NH-16
Route 108 climbs through Smugglers’ Notch, a narrow gap between Mount Mansfield and Spruce Peak closed to trucks and trailers, with hairpin turns beneath boulder fields — one of the most dramatic short drives in New England before the road opens back up toward New Hampshire.
📸 Kancamagus Highway — Sugar Hill Overlook & Sabbaday Falls
~1.5–2 hours with stops · Free (WMNF parking pass $5/day)
New Hampshire’s Route 112 crosses forty-four unbroken miles of White Mountain National Forest with no gas stations or towns — Sugar Hill Overlook is the highway’s best panoramic pull-off, and Sabbaday Falls is a flat 0.6-mile round-trip walk to a tiered waterfall through a mossy gorge.
🍽️ Lunch — Moat Mountain Smokehouse & Brewing Co., North Conway
~1 hour · Est. $18–26 USD / person
A wood-fired smokehouse and brewery in the heart of North Conway, with a mountain view from the back deck — order the smoked brisket or the trout plate and a flight of the house-brewed beers before the final drive home.
Moat Mountain Smokehouse & Brewing Co. · +1 603 356 6381 · www.moatmountain.com
🚗 Self-Drive — North Conway to Boston Logan Airport
~2.5–3 hours · via NH-16 & I-95
The drive back south runs through the Lakes Region before rejoining the interstate for Boston — plan for Sunday-afternoon traffic on I-95 during peak foliage weekends, and return the rental car with a full tank.
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