33 days in Vermont Itinerary

33 days in Vermont Itinerary

Created using Inspirock Vermont trip planner

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Route & dates

33 days in Vermont Itinerary

Start: San Antonio
Fly:  9​h
1
Shelburne
— 7 nights
Drive:  1​h 45​min
2
Saint Johnsbury
— 6 nights
Drive:  1​h 30​min
3
Woodstock
— 7 nights
Drive:  1​h 15​min
4
Brattleboro
— 6 nights
Drive:  1​h 15​min
5
Manchester
— 6 nights
bus + Fly:  10​h 30​min
End: San Antonio

7
nights
Shelburne

Shelburne ©
Shelburne is a town in southwestern Chittenden County, Vermont, in the United States. Explore Shelburne's surroundings by going to Cabot Farmers' Store (in Waterbury Center), Stowe (Mount Mansfield State Forest, Gold Brook Covered Bridge (Emily's Covered Bridge), & more) and Beer Tastings & Tours (in Burlington). There's still lots to do: examine the collection at Shelburne Museum, get a sense of history and politics at Vermont State House, brush up on your knowledge of spirits at Boyden Valley Winery & Spirits, and experience rural life at Shelburne Farms.

For traveler tips, ratings, where to stay, and tourist information, go to the Shelburne trip itinerary planner .

San Antonio to Shelburne is an approximately 9-hour flight. You can also do a combination of flight and ferry; or drive. The time zone difference moving from Central Standard Time to Eastern Standard Time is 1 hour. Prepare for colder weather when traveling from San Antonio in October: high temperatures in Shelburne hover around 62°F and lows are around 44°F. Finish up your sightseeing early on the 22nd (Tue) so you can go by car to Saint Johnsbury.

Things to do in Shelburne

Parks Outdoors Winter Sports

Side Trips

Burlington, Stowe, Boyden Valley Winery & Spirits, 1st Republic Brewing Company, Vermont State House
Highlights from your plan
Shelburne Museum ©
Shelburne Museum
Stowe Recreation Path ©
Stowe Recreation Path
Shelburne Farms ©
Shelburne Farms

6
nights
Saint Johnsbury

Saint Johnsbury ©
St. Explore Saint Johnsbury's surroundings by going to Montpelier (Morse Farm Maple Sugarworks & Bragg Farm Sugar House & Gift Shop), Barre (Hope Cemetery & Rock of Ages Granite Quarry) and Sunset Lake Floating Bridge (in Brookfield). The adventure continues: walk around Dog Mountain Home of Stephen Huneck Gallery, get to know the fascinating history of The Long Trail, contemplate the long history of Tea at the Governor's House, and stroll through Lamoille Valley Rail Trail.

To find more things to do, photos, other places to visit, and more tourist information, use the Saint Johnsbury trip maker website .

You can drive from Shelburne to Saint Johnsbury in 2 hours. In October, daytime highs in Saint Johnsbury are 60°F, while nighttime lows are 40°F. Cap off your sightseeing on the 28th (Mon) early enough to go by car to Woodstock.

Things to do in Saint Johnsbury

Parks Historic Sites Nature

Side Trips

Barre, Montpelier, East Burke, Fisher Railroad Bridge, Jay Peak Pump House
Highlights from your plan
Fairbanks Museum and Planetarium ©
Fairbanks Museum and Planetarium
St. Johnsbury Athenaeum ©
St. Johnsbury Athenaeum

7
nights
Woodstock

Woodstock ©
Woodstock is the shire town of Windsor County, Vermont, United States. Explore Woodstock's surroundings by going to Killington Resort (in Killington), Bennington (Bennington Museum, Bennington Battle Monument, & more) and Plymouth Artisan Cheese (in Plymouth). The adventure continues: experience rural life at Sugarbush Farm, make a trip to Taftsville Covered Bridge, delve into the lush surroundings at Mount Tom, and contemplate the long history of Marsh - Billings - Rockefeller National Historical Park.

To find more things to do, maps, other places to visit, and tourist information, use the Woodstock trip tool .

Getting from Saint Johnsbury to Woodstock by car takes about 1.5 hours. In October, plan for daily highs up to 62°F, and evening lows to 40°F. Finish up your sightseeing early on the 4th (Mon) so you can go by car to Brattleboro.

Things to do in Woodstock

Parks Historic Sites Nature

Side Trips

Bennington, Quechee, Plymouth, Windsor, Montshire Museum of Science
Highlights from your plan
Sugarbush Farm ©
Sugarbush Farm
Billings Farm & Museum ©
Billings Farm & Museum

6
nights
Brattleboro

Brattleboro ©
Brattleboro, originally Brattleborough, is a town in Windham County, Vermont, United States. Get out of town with these interesting Brattleboro side-trips: Dover (Mount Snow Resort & Skyline Overlook), Honora Winery & Vineyard (in Jacksonville) and Vermont Shepherd (in Putney). There's much more to do: experience rural life at Robb Family Farm, tour the pleasant surroundings at Retreat Trails, stroll around Living Memorial Park, and snap pictures at Creamery Covered Bridge.

For traveler tips, reviews, and more tourist information, use the Brattleboro online trip itinerary maker .

You can drive from Woodstock to Brattleboro in 1.5 hours. In November, plan for daily highs up to 48°F, and evening lows to 27°F. Wrap up your sightseeing on the 10th (Sun) early enough to drive to Manchester.

Things to do in Brattleboro

Parks Trails Outdoors

Side Trips

Putney, Wilmington, Dover, Marlboro, West Dummerston Covered Bridge
Highlights from your plan
Mount Snow Resort ©
Mount Snow Resort
Robb Family Farm ©
Robb Family Farm
Creamery Covered Bridge ©
Creamery Covered Bridge

6
nights
Manchester

Manchester ©
Manchester is a town in, and one of two shire towns (county seats) of, Bennington County, Vermont, United States. Explore the numerous day-trip ideas around Manchester: TimberQuest Park (in Londonderry), Grafton (Jud Hartmann Gallery & Grafton Historical Society) and Jamaica State Park (in Jamaica). There's much more to do: take in nature's colorful creations at Hildene, The Lincoln Family Home, look for gifts at Vermont Country Store, browse the collection at Whiting Library, and view the masterpieces at Southern Vermont Arts Center.

To find ratings, reviews, maps, and tourist information, go to the Manchester trip planner .

Getting from Brattleboro to Manchester by car takes about 1.5 hours. In November, plan for daily highs up to 49°F, and evening lows to 29°F. On the 16th (Sat), wrap the sightseeing up by early afternoon so you can travel back home.

Things to do in Manchester

Parks Nature Museums

Side Trips

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

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