55 days in Vermont Itinerary

55 days in Vermont Itinerary

Created using Inspirock Vermont trip planner

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Route & dates

55 days in Vermont Itinerary

Start: Florianopolis
Fly + Drive:  20​h 45​min
1
Stowe
— 11 nights
Drive:  1​h 15​min
2
Jay
— 8 nights
Drive:  1​h 15​min
3
Saint Johnsbury
— 8 nights
Drive:  1​h 30​min
4
Woodstock
— 8 nights
Drive:  1​h 30​min
5
Manchester
— 7 nights
Drive:  1​h 30​min
6
Middlebury
— 10 nights
Drive + Fly:  22​h 45​min
End: Florianopolis

11
nights
Stowe

Stowe ©
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.
Get out of town with these interesting Stowe side-trips: Burlington (Burlington Bike Path, Church Street Marketplace, & more), Jeffersonville (Quarry Hill Farm & Smugglers' Notch Resort) and Boyden Valley Winery & Spirits (in Cambridge). There's much more to do: trek along Stowe Recreation Path, ski along the peaceful trails at Trapp Family Lodge Outdoor Center, cool off at Stowe Mountain Resort, and stroll through Stowe Mountain.

For ratings, traveler tips, more things to do, and tourist information, you can read our Stowe online sightseeing planner .

Florianopolis, Brazil to Stowe is an approximately 21-hour combination of flight and car. You can also do a combination of flight and bus. The time zone difference moving from Brasilia Time (BRT) to Eastern Standard Time (EST) is minus 2 hours. Traveling from Florianopolis in December, things will get colder in Stowe: highs are around 0°C and lows about -9°C. Finish your sightseeing early on the 20th (Fri) to allow enough time to drive to Jay.

Things to do in Stowe

Parks Outdoors Winter Sports

Side Trips

Burlington, Montpelier, Jeffersonville, Barre, Shelburne Farms
Highlights from your plan
Stowe Recreation Path ©
Stowe Recreation Path
Mount Mansfield State Forest ©
Mount Mansfield State Forest
Stowe Mountain Resort ©
Stowe Mountain Resort

8
nights
Jay

Jay ©
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: Newport Bike Path (in Newport), Missisquoi National Wildlife Refuge (in Swanton) and 14th Star Brewing Company (in Saint Albans). There's much more to do: make a splash at Jay Peak Pump House, don't miss a visit to MAC Center for the Arts, get engrossed in the history at Old Stone House Museum, and take in the spiritual surroundings of St. Anne's Shrine.

To see ratings, traveler tips, reviews, and other tourist information, go to the Jay day trip website .

Drive from Stowe to Jay in 1.5 hours. In December in Jay, expect temperatures between -1°C during the day and -9°C at night. Finish up your sightseeing early on the 28th (Sat) so you can go by car to Saint Johnsbury.

Things to do in Jay

Parks Outdoors Wildlife

Side Trips

Isle La Motte, Newport, 14th Star Brewing Company, Jed's Maple Products, Missisquoi National Wildlife Refuge
Highlights from your plan
Jay Peak Resort ©
Jay Peak Resort
Cold Hollow Sculpture Park ©
Cold Hollow Sculpture Park
St. Anne's Shrine ©
St. Anne's Shrine

8
nights
Saint Johnsbury

Saint Johnsbury ©
St. Explore Saint Johnsbury's surroundings by going to Sunset Lake Floating Bridge (in Brookfield), Glover (Bread and Puppet Theater & Museum of Everyday Life) and East Burke (Mount Pisgah, Burke Mountain Resort, & more). And it doesn't end there: walk around Dog Mountain Home of Stephen Huneck Gallery, get your bearings at St. Johnsbury Athenaeum, admire the striking features of The Dog Chapel, and get lost in a book at Charles D. Brainerd Library.

To see where to stay, other places to visit, maps, and tourist information, you can read our Saint Johnsbury trip itinerary planner.

Traveling by car from Jay to Saint Johnsbury takes 1.5 hours. Expect a daytime high around 0°C in December, and nighttime lows around -9°C. Wrap up your sightseeing by early afternoon on the 5th (Sun) to allow time for the car ride to Woodstock.

Things to do in Saint Johnsbury

Parks Nature Outdoors

Side Trips

Groton, East Burke, Glover, Maidstone State Park, Charles D. Brainerd Library
Highlights from your plan
St. Johnsbury Athenaeum ©
St. Johnsbury Athenaeum
Fairbanks Museum and Planetarium ©
Fairbanks Museum and Planetarium

8
nights
Woodstock

Woodstock ©
Woodstock is the shire town of Windsor County, Vermont, United States. Get out of town with these interesting Woodstock side-trips: Papermill Village Bridge (in North Bennington), Bennington (Bennington Museum & Bennington Battle Monument) and Robert Frost Stone House Museum (in Shaftsbury). And it doesn't end there: relax in the rural setting at Sugarbush Farm, fly down the slopes at Mount Snow Resort, engage your brain at Montshire Museum of Science, and explore the wealth of natural beauty at Marsh - Billings - Rockefeller National Historical Park.

For other places to visit, ratings, photos, and more tourist information, read Woodstock day trip planning site .

Traveling by car from Saint Johnsbury to Woodstock takes 1.5 hours. In January, daytime highs in Woodstock are -1°C, while nighttime lows are -13°C. Finish up your sightseeing early on the 13th (Mon) so you can go by car to Manchester.

Things to do in Woodstock

Parks Winter Sports Outdoors

Side Trips

Quechee, Bennington, Windsor, Plymouth, Okemo Mountain Resort
Highlights from your plan
Sugarbush Farm ©
Sugarbush Farm
Billings Farm & Museum ©
Billings Farm & Museum
Killington Resort ©
Killington Resort

7
nights
Manchester

Manchester ©
Manchester is a town in, and one of two shire towns (county seats) of, Bennington County, Vermont, United States. Get out of town with these interesting Manchester side-trips: West Dummerston Covered Bridge (in Dummerston), Brattleboro (Saxtons River Distillery & Hermit Thrush Brewery) and Skyline Overlook (in Dover). There's still lots to do: take in nature's colorful creations at Hildene, The Lincoln Family Home, take in the dramatic scenery at Lye Brook Falls, glide through natural beauty at Grafton Trails & Outdoor Center, and fly down the slopes at Bromley Mountain.

For other places to visit, maps, ratings, and other tourist information, go to the Manchester journey builder .

Getting from Woodstock to Manchester by car takes about 1.5 hours. Other options: take a bus. In January, daily temperatures in Manchester can reach 0°C, while at night they dip to -12°C. Finish your sightseeing early on the 20th (Mon) so you can drive to Middlebury.

Things to do in Manchester

Parks Winter Sports Outdoors

Side Trips

Arlington, Londonderry, Grafton, Brattleboro, Weston
Highlights from your plan
Hildene, The Lincoln Family Home ©
Hildene, The Lincoln Family Home
Vermont Country Store ©
Vermont Country Store
Equinox Preservation Trust ©
Equinox Preservation Trust

10
nights
Middlebury

Middlebury ©
Middlebury is the shire town (county seat) of Addison County, Vermont, United States. Venture out of the city with trips to Warren (Sugarbush Resort & Ole's Cross Country Center), Middlebury College Snow Bowl (in Hancock) and D.A.R. State Park (in Addison). Next up on the itinerary: see the interesting displays at Shelburne Museum, explore the world behind art at Mahaney Center for the Arts, cruise along Lincoln Gap Road, and look for gifts at Danforth Pewter.

For traveler tips, reviews, more things to do, and more tourist information, read Middlebury day trip planning website .

Traveling by car from Manchester to Middlebury takes 1.5 hours. In January, daily temperatures in Middlebury can reach -1°C, while at night they dip to -12°C. Finish up your sightseeing early on the 30th (Thu) so you can travel back home.

Things to do in Middlebury

Outdoors Parks Winter Sports

Side Trips

Shelburne, Brandon, Charlotte, Ferrisburgh, Warren
Highlights from your plan
Sugarbush Resort ©
Sugarbush Resort
Shelburne Museum ©
Shelburne Museum
Lincoln Peak Vineyard ©
Lincoln Peak Vineyard

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