40 days in Vermont Itinerary

Created using Klarna Trips Vermont trip itinerary planner
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Make it your trip
Fly
1
Burlington
— 10 nights
Drive
2
Jay
— 8 nights
Drive
3
Dover
— 10 nights
Drive
4
Woodstock
— 11 nights
Fly to Nashville, Bus to Huntsville

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Burlington — 10 nights

Burlington is the most populous city in the U.S. state of Vermont and the seat of Chittenden County. Change things up with these side-trips from Burlington: Jeffersonville ( Smugglers' Notch Distillery - Maple Products - Gift Shop - Local Products & Smugglers' Notch Resort), Bolton Valley Resort (in Bolton Valley) and Valley Dream Farm (in Cambridge). And it doesn't end there: hunt for treasures at Church Street Marketplace, walk around Waterfront Park, see what you can catch with 3rd Alarm Charters & Guide Service, and engage your brain at ECHO, Leahy Center for Lake Champlain.

To find ratings, reviews, more things to do, and tourist information, read our Burlington trip itinerary planning app.

Huntsville to Burlington is an approximately 6.5-hour flight. You can also drive; or do a combination of bus and train. The time zone difference when traveling from Huntsville to Burlington is 1 hour. In December, Burlington is little chillier than Huntsville - with highs of 36°F and lows of 23°F. Wrap up your sightseeing on the 4th (Wed) to allow time to drive to Jay.
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Outdoors · Parks · Winter Sports · Breweries & Distilleries
Side Trips
Find places to stay Dec 25 — Jan 4:

Jay — 8 nights

Jay is one of the northernmost towns in Orleans County, Vermont, United States, located on the Canada–US border. Change things up with these side-trips from Jay: Tea at the Governor's House (in Hyde Park), Eden Dogsledding (in Eden Mills) and Saint Johnsbury (The Dog Chapel & Dog Mountain Home of Stephen Huneck Gallery). categoryPhrases.sentence.On_the_day_spend_an_exhilarating_day_on_the_slopes_at. There's lots more to do: hit the slopes at Jay Peak Resort, engage your brain at Museum of Everyday Life, relax and rejuvenate at Vermont Salt Cave Spa & Halotherapy Center, and explore the landscape on two wheels at Newport Bike Path.

To see other places to visit, more things to do, reviews, and other tourist information, read Jay route planner.

Traveling by car from Burlington to Jay takes 1.5 hours. Prepare for slightly colder weather when traveling from Burlington in January: high temperatures in Jay hover around 25°F and lows are around 8°F. Finish up your sightseeing early on the 12th (Thu) so you can go by car to Dover.
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Parks · Outdoors · Winter Sports · Nature
Side Trips
Find places to stay Jan 4 — 12:

Dover — 10 nights

Dover is a town in Windham County, Vermont, United States. You'll find plenty of places to visit near Dover: Arlington (Bridge at the Green & Equinox Mountain), Manchester (North Meadow Farm, Lye Brook Falls, &more) and Weston (Mill Museum & Vermont Country Store). categoryPhrases.sentence.On_the_day_spend_an_exhilarating_day_on_the_slopes_at. There's still lots to do: stroll through Mount Snow Resort, indulge in some personalized pampering at Serenity Spa, play a few rounds at Haystack Golf Club, and fly down the slopes at Magic Mountain.

To find photos, other places to visit, and other tourist information, you can read our Dover road trip planning tool.

Drive from Jay to Dover in 3.5 hours. When traveling from Jay in January, plan for a bit warmer days and about the same nights in Dover: temperatures range from 32°F by day to 13°F at night. Finish your sightseeing early on the 22nd (Sun) to allow enough time to drive to Woodstock.
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Parks · Outdoors · Winter Sports · Museums
Side Trips
Find places to stay Jan 12 — 22:

Woodstock — 11 nights

Woodstock is the shire town of Windsor County, Vermont, United States. Venture out of the city with trips to Weston Priory (in Weston), Foley Brothers Brewing (in Brandon) and Ludlow (Jackson Gore Ski Area & Okemo Mountain Resort). Spend the 27th (Fri) exploring nature at Marsh - Billings - Rockefeller National Historical Park. There's still lots to do: contemplate the long history of Billings Farm & Museum, take a peaceful walk through Mount Tom, engage your brain at Montshire Museum of Science, and make a trip to Woodstock Vermont Historical Society.

To find other places to visit, where to stay, traveler tips, and tourist information, read our Woodstock trip itinerary builder site.

You can drive from Dover to Woodstock in 2 hours. In January in Woodstock, expect temperatures between 30°F during the day and 11°F at night. Wrap up your sightseeing by early afternoon on the 2nd (Thu) to allow enough time to travel back home.
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Parks · Outdoors · Nature · Winter Sports
Side Trips
Find places to stay Jan 22 — Feb 2:

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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