16 days in Vermont Itinerary

Created using Klarna Trips Vermont visit planner
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Make it your trip
Drive
1
Woodstock
— 5 nights
Drive
2
Stowe
— 5 nights
Drive
3
Bennington
— 5 nights
Drive

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Woodstock — 5 nights

Woodstock is the shire town of Windsor County, Vermont, United States. Explore Woodstock's surroundings by going to Marble Bridge (in Proctor), Vermont Bike & Brew (in Thetford) and Killington Resort (in Killington). The adventure continues: experience rural life at Sugarbush Farm, indulge your thirst for a good beer at Harpoon Brewery, don't miss a visit to Woodstock Vermont Historical Society, and take in breathtaking views at Quechee Gorge.

For other places to visit, more things to do, traveler tips, and more tourist information, go to the Woodstock trip itinerary site.

Hartford to Woodstock is an approximately 2.5-hour car ride. You can also do a combination of bus and flight; or do a combination of train and taxi. Expect a bit cooler temperatures when traveling from Hartford in November; daily highs in Woodstock reach 47°F and lows reach 28°F. Finish your sightseeing early on the 5th (Mon) to allow enough time to drive to Stowe.
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Parks · Outdoors · Museums · Wildlife
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Stowe — 5 nights

The Ski Capital of the East

Stowe bustles in winter when skiers and snowboarders flock here to challenge themselves on the long, steep trails careening down Vermont's tallest peak, Mt.
Explore Stowe's surroundings by going to Burlington (World's Tallest Filing Cabinet, Church Street Marketplace, &more), Shelburne Farms (in Shelburne) and Montpelier (Vermont State House & Morse Farm Maple Sugarworks). There's still lots to do: stroll through Stowe Recreation Path, indulge your thirst for a good beer at The Alchemist Brewery, take a memorable drive along Smugglers Notch State Park, and indulge in some personalized pampering at Spa at the Essex.

For traveler tips, reviews, photos, and tourist information, refer to the Stowe trip planner.

Drive from Woodstock to Stowe in 1.5 hours. Alternatively, you can do a combination of taxi and train; or do a combination of bus and train. Expect a daytime high around 33°F in December, and nighttime lows around 17°F. Finish up your sightseeing early on the 10th (Sat) so you can go by car to Bennington.
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Parks · Breweries & Distilleries · Outdoors · Historic Sites
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Bennington — 5 nights

Bennington is a town in Bennington County, Vermont, in the United States. Explore the numerous day-trip ideas around Bennington: Manchester (North Meadow Farm, Lye Brook Falls, &more), Vermont Country Store (in Weston) and Taylor Farm (in Londonderry). Next up on the itinerary: get great views at Bennington Battle Monument, take your sightseeing to a higher altitude at Equinox Mountain, cruise along Mount Equinox Skyline Drive, and brush up on your knowledge of spirits at Saxtons Distillery.

For maps, ratings, more things to do, and other tourist information, refer to the Bennington route maker.

Traveling by car from Stowe to Bennington takes 3 hours. Alternatively, you can do a combination of train and car; or take a bus. Traveling from Stowe in December, expect Bennington to be a bit warmer, temps between 39°F and 23°F. Finish your sightseeing early on the 15th (Thu) so you can drive back home.
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Museums · Shopping · Nature · Historic Sites
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Vermont travel guide

4.4
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.
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