14 days in Vermont Itinerary

14 days in Vermont Itinerary

Created using Inspirock Vermont route planner

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Route & dates

14 days in Vermont Itinerary

Start: Washington DC
Fly + Drive:  6​h 30​min
1
Bennington
— 3 nights
Drive:  1​h 45​min
2
Woodstock
— 3 nights
Drive:  1​h 30​min
3
Saint Johnsbury
— 2 nights
Drive:  1​h 45​min
4
Burlington
— 5 nights
Fly:  3​h 30​min
End: Washington DC

3
nights
Bennington

Bennington ©
Bennington is a town in Bennington County, Vermont, in the United States. Explore the numerous day-trip ideas around Bennington: Equinox Mountain (in Arlington), Vermont Country Store (in Weston) and Manchester (Hildene, The Lincoln Family Home, Lye Brook Falls, & more). There's still lots to do: pause for some photo ops at Bennington Battle Monument, don't miss a visit to Silk Road Covered Bridge, explore the different monuments and memorials at The Old First Church, and take in the views from Papermill Village Bridge.

For traveler tips, more things to do, where to stay, and more tourist information, you can read our Bennington day trip website .

Washington DC to Bennington is an approximately 6.5-hour combination of flight and car. You can also drive. Expect little chillier temperatures when traveling from Washington DC in October; daily highs in Bennington reach 62°F and lows reach 41°F. Finish your sightseeing early on the 16th (Wed) to allow enough time to drive to Woodstock.

Things to do in Bennington

Parks Nature Museums

Side Trips

Manchester, Arlington, Vermont Country Store, Mad Tom Orchard
Highlights from your plan
Hildene, The Lincoln Family Home ©
Hildene, The Lincoln Family Home
Bennington Battle Monument ©
Bennington Battle Monument
Bennington Museum ©
Bennington Museum

3
nights
Woodstock

Woodstock ©
Woodstock is the shire town of Windsor County, Vermont, United States. Take a break from Woodstock with a short trip to Killington Resort in Killington, about 34 minutes away. There's much more to do: experience rural life at Sugarbush Farm, explore the wealth of natural beauty at Marsh - Billings - Rockefeller National Historical Park, pick up a one of a kind souvenir at Cabot Queechee Store, and identify plant and animal life at Vermont Institute of Natural Science (VINS) Nature Center.

Take the guesswork out of planning a Woodstock vacation by using our trip itinerary maker.

You can drive from Bennington to Woodstock in 2 hours. October in Woodstock sees daily highs of 62°F and lows of 40°F at night. Finish up your sightseeing early on the 19th (Sat) so you can go by car to Saint Johnsbury.

Things to do in Woodstock

Parks Nature Historic Sites

Side Trips

Quechee, Montshire Museum of Science, Killington Resort
Highlights from your plan
Quechee Gorge ©
Quechee Gorge
Sugarbush Farm ©
Sugarbush Farm
Billings Farm & Museum ©
Billings Farm & Museum

2
nights
Saint Johnsbury

Saint Johnsbury ©
St. On the 20th (Sun), walk around Dog Mountain Home of Stephen Huneck Gallery, make a trip to Bragg Farm Sugar House & Gift Shop, and then explore the different monuments and memorials at Hope Cemetery. Keep things going the next day: contemplate the waterfront views at Lake Willoughby, get advice or help at St. Johnsbury Athenaeum, and then admire the striking features of The Dog Chapel.

Plan a Saint Johnsbury trip in moments using our itinerary builder.

Traveling by car from Woodstock to Saint Johnsbury takes 1.5 hours. In October, plan for daily highs up to 60°F, and evening lows to 40°F. Finish your sightseeing early on the 21st (Mon) to allow enough time to drive to Burlington.

Things to do in Saint Johnsbury

Parks Nature Historic Sites

Side Trips

Lake Willoughby, Hope Cemetery, Bragg Farm Sugar House & Gift Shop
Highlights from your plan
St. Johnsbury Athenaeum ©
St. Johnsbury Athenaeum
Bragg Farm Sugar House & Gift Shop ©

5
nights
Burlington

Burlington ©
Burlington is the most populous city in the U.S. Get out of town with these interesting Burlington side-trips: Montpelier (Vermont State House & Morse Farm Maple Sugarworks), Cabot Farmers' Store (in Waterbury Center) and Stowe (Smugglers Notch State Park, Stowe Recreation Path, & more). And it doesn't end there: browse the eclectic array of goods at Church Street Marketplace, get curious at ECHO, Leahy Center for Lake Champlain, contemplate the long history of Shelburne Farms, and indulge your thirst for a good beer at 1st Republic Brewing Company.

For ratings, maps, and other tourist information, read our Burlington holiday planner.

Drive from Saint Johnsbury to Burlington in 2 hours. In October in Burlington, expect temperatures between 62°F during the day and 44°F at night. Wrap up your sightseeing on the 26th (Sat) to allow time to travel back home.

Things to do in Burlington

Parks Outdoors Nature

Side Trips

Stowe, Shelburne, Montpelier, Cabot Farmers' Store, 1st Republic Brewing Company
Highlights from your plan
Church Street Marketplace ©
Church Street Marketplace
Burlington Bike Path ©
Burlington Bike Path
Waterfront Park ©
Waterfront Park

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