14 days in Vermont Itinerary

14 days in Vermont Itinerary

Created using Inspirock Vermont travel route planner

©
Make it your trip
Fly
1
Burlington
— 5 nights
Drive
2
Woodstock
— 3 nights
Drive
3
Bennington
— 4 nights
Drive to Bradley International Airport, Fly to Malpensa International Airport

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Burlington

— 5 nights
Burlington is the most populous city in the U.S. Explore Burlington's surroundings by going to Montpelier (Bragg Farm Sugar House & Gift Shop & Morse Farm Maple Sugarworks) and Stowe (Nebraska Knoll Sugar Farm, Mount Mansfield State Forest, &more). And it doesn't end there: hunt for treasures at Church Street Marketplace, steep yourself in history at Shelburne Farms, trek along Burlington Bike Path, and examine the collection at Shelburne Museum.

To find more things to do, other places to visit, reviews, and more tourist information, go to the Burlington trip planner.

Milan, Italy to Burlington is an approximately 15.5-hour flight. The time zone difference when traveling from Milan to Burlington is minus 6 hours. Traveling from Milan in October, expect a bit cooler with lows of 7°C in Burlington. Cap off your sightseeing on the 25th (Mon) early enough to go by car to Woodstock.

Things to do in Burlington

Parks · Outdoors · Nature · Breweries & Distilleries

Side Trips

Woodstock

— 3 nights
Woodstock is the shire town of Windsor County, Vermont, United States. Woodstock is known for historic sites, nature, and shopping. Your plan includes some of its best attractions: relax in the rural setting at Sugarbush Farm, steep yourself in history at Billings Farm & Museum, don't miss a visit to Taftsville Covered Bridge, and explore the striking landscape of Marsh - Billings - Rockefeller National Historical Park.

For ratings, photos, maps, and other tourist information, read Woodstock trip planning website.

Drive from Burlington to Woodstock in 2 hours. Alternatively, you can take a bus. In October in Woodstock, expect temperatures between 19°C during the day and 5°C at night. Wrap up your sightseeing on the 28th (Thu) to allow time to drive to Bennington.

Things to do in Woodstock

Parks · Nature · Historic Sites · Museums

Side Trip

Bennington

— 4 nights
Bennington is a town in Bennington County, Vermont, in the United States. Explore the numerous day-trip ideas around Bennington: Creamery Covered Bridge (in Brattleboro), Manchester (Equinox Preservation Trust, Hildene, The Lincoln Family Home, &more) and Vermont Country Store (in Weston). And it doesn't end there: pause for some photo ops at Bennington Battle Monument, make a trip to Silk Road Covered Bridge, admire the masterpieces at Bennington Museum, and snap pictures at Papermill Village Bridge.

To find traveler tips, photos, ratings, and tourist information, use the Bennington trip itinerary maker app.

Getting from Woodstock to Bennington by car takes about 2 hours. Other options: take a bus. In October, daytime highs in Bennington are 19°C, while nighttime lows are 5°C. Wrap up your sightseeing on the 1st (Mon) to allow time to travel back home.

Things to do in Bennington

Historic Sites · Outdoors · Parks · Museums

Side Trips

Vermont travel guide

4.5
Gift & Specialty Shops · Ski Areas · Hiking Trails
The Green Mountain State
Known for its autumn foliage and maple syrup, Vermont is one of the country's smallest states in terms of both population and geographic area. Despite its small size and mostly rural character, the state boasts many picturesque places to visit, including Lake Champlain, one of the nation's largest freshwater bodies. Split in half by the Green Mountains--a popular holiday destination for hiking and skiing--Vermont features a rolling landscape dotted with farms and quaint towns known for their family-run inns, antique shops, and restaurants. Be sure to explore the state's many wild areas while on vacation, but beware of the so-called "mud season," a period of a few weeks when the state's unpaved roads become undrivable due to spring thaw.