Vermont Weekend Itinerary: 3 Days in New England's Most Charming State
Three days in Vermont is enough time to experience the best of New England — a weekend itinerary that takes you through Woodstock, Stowe, and the Green Mountains, with covered bridges, maple syrup, craft beer, and spectacular scenery along the way.
Part of the Destination Guide
Vermont — Destination Guide
Three days in Vermont is enough time to experience the best of New England. This weekend itinerary takes you through Woodstock, Quechee Gorge, Stowe, and the Green Mountains — with covered bridges, maple syrup farms, craft beer, and some of the most beautiful scenery in America along the way.
It works beautifully in any season, but it's particularly spectacular during fall foliage (early to mid-October) and during the summer wildflower season (June–July).
Day 1: Arrive in Woodstock — Vermont's Most Perfect Village
Afternoon: Arrive in Woodstock
Woodstock is the ideal starting point for a Vermont weekend — the state's most beautiful village, with perfectly preserved Federal and Greek Revival architecture, covered bridges, and a village green that looks like it was designed for a postcard.
Check In: The Woodstock Inn & Resort is the finest hotel in Woodstock, with beautiful rooms and an excellent restaurant. The Kedron Valley Inn (nearby South Woodstock) is a beautiful alternative.
Afternoon Exploration: Walk the village — the green, the covered bridges, the shops on Elm Street. Allow 1–2 hours.
Quechee Gorge: Drive 6 miles east to Quechee Gorge — Vermont's "Little Grand Canyon," a dramatic 165-foot gorge carved by the Ottauquechee River. The gorge is accessible via a short walk from the road and is spectacular in any season.
Evening: Dinner in Woodstock
The Prince and the Pauper — the finest restaurant in Woodstock, with excellent New England cuisine in a beautiful historic setting. Reservations recommended.
Alternative: The Woodstock Inn's Red Rooster restaurant is also excellent, with a beautiful setting and a menu that celebrates Vermont's agricultural heritage.
Day 2: Covered Bridges, Maple Syrup & the Drive North
Morning: Covered Bridge Tour
Start the morning with a covered bridge tour of Windsor County — the highest concentration of covered bridges in Vermont. The Taftsville Covered Bridge (1836) and the Middle Bridge in the heart of Woodstock village are both beautiful.
Sugarbush Farm: Drive 3 miles up Hillside Road from Woodstock to Sugarbush Farm — a beautiful working farm with excellent maple syrup and cheese. The farm is open year-round and offers tours and tastings.
Late Morning: Drive North on Route 12
Take Route 12 north from Woodstock toward Montpelier — one of Vermont's most scenic drives, passing through beautiful hill country with excellent views of the Green Mountains.
Barnard: A beautiful small town with Silver Lake State Park — excellent for a short walk or a swim in summer.
Montpelier: Vermont's charming state capital is worth a brief stop — the beautiful State House, the Vermont Historical Society Museum, and the excellent La Brioche bakery.
Afternoon: Arrive in Stowe
Continue north on I-89 and Route 100 to Stowe — Vermont's most famous mountain town, with world-class skiing, excellent hiking, and a charming village.
The Stowe Recreation Path: A 5.3-mile paved path along the West Branch River — excellent for an afternoon walk or bike ride.
The Trapp Family Lodge: Drive up the hill to the famous lodge founded by the von Trapp family (of "Sound of Music" fame) for a beautiful view of the surrounding mountains and an excellent afternoon snack.
Evening: Dinner in Stowe
Hen of the Wood — consistently rated one of the finest restaurants in Vermont, with exceptional farm-to-table cuisine. Reservations essential.
The Alchemist Brewery: Stop for a pint of Heady Topper — one of the most celebrated craft beers in America — at the Alchemist's Stowe brewery.
Where to Stay:
- Stowe Mountain Lodge — the finest resort in Stowe, with beautiful mountain views and excellent amenities
- Topnotch Resort — a beautiful spa resort with excellent facilities
Day 3: Mount Mansfield & the Drive Home
Early Morning: Sunrise on Mount Mansfield
Wake up early and drive to the Stowe Mountain Resort gondola (or the Toll Road) for sunrise on Mount Mansfield — Vermont's highest peak (4,395 feet). The views from the summit are extraordinary on a clear morning.
Hiking Alternative: The Sunset Ridge Trail (3.7 miles one way, strenuous) from Underhill State Park is an excellent hiking route to the summit for those who prefer to earn the view.
Morning: Smugglers' Notch
Drive Route 108 through Smugglers' Notch — a dramatic mountain pass between Stowe and Jeffersonville, with 1,000-foot cliffs and enormous boulders. The road is closed in winter but spectacular in summer and fall.
Sterling Pond Trail (1.5 miles one way, moderate) — a beautiful trail to a beautiful alpine pond at 3,000 feet elevation.
Afternoon: Route 100 South
Take Route 100 south from Stowe — the "Main Street of Vermont" — through the Mad River Valley and the heart of the Green Mountains.
Waitsfield and Warren: Two beautiful villages in the Mad River Valley, with excellent restaurants and shops. Lawson's Finest Liquids (Warren) is a must-stop for craft beer enthusiasts.
Ben & Jerry's Factory (Waterbury): The famous ice cream factory is just off I-89 in Waterbury — a fun stop for families and ice cream enthusiasts.
Late Afternoon: Depart Vermont
Take I-89 south toward Burlington and then south toward your destination. The drive from Stowe to Boston is about 3.5 hours; to New York City, about 5 hours.
Practical Tips
Fall Foliage: If visiting in October, check the Vermont foliage report at foliage.vermont.gov before finalizing your itinerary. Peak foliage timing varies by year and elevation.
Reservations: Book hotels and restaurants well in advance for fall foliage season (early to mid-October) — Vermont fills up quickly.
Route 100: The most scenic route through Vermont, running north-south through the heart of the state. Use it whenever possible.
For more Vermont adventures, see our Vermont Small Towns Guide, Vermont Fall Foliage Guide, Vermont Hiking Guide, Vermont Farm-to-Table Food Guide, Vermont Covered Bridges Guide, and Where to Stay in Vermont.
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