25 days in Vermont Itinerary

25 days in Vermont Itinerary

Created using Inspirock Vermont holiday maker

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Route & dates

25 days in Vermont Itinerary

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

5
nights
Shelburne

Shelburne ©
Shelburne is a town in southwestern Chittenden County, Vermont, in the United States. Explore Shelburne's surroundings by going to Stowe (Mount Mansfield State Forest, Moss Glen Falls, & more), Cabot Farmers' Store (in Waterbury Center) and Beer Tastings & Tours (in Burlington). And it doesn't end there: examine the collection at Shelburne Museum, stroll around Waterfront Park, steep yourself in history at Ethan Allen Homestead, and indulge your thirst for a good beer at Magic Hat Brewing Company.

Before you visit Shelburne, use our trip planner to discover what you can do and see there.

Chicago to Shelburne is an approximately 5.5-hour flight. You can also drive; or do a combination of train and taxi. The time zone difference moving from Central Standard Time to Eastern Standard Time is 1 hour. Plan for slightly colder nights when traveling from Chicago in October since evenings lows in Shelburne dip to 44°F. Finish your sightseeing early on the 8th (Tue) to allow enough time to drive to Saint Johnsbury.

Things to do in Shelburne

Parks Outdoors Nature

Side Trips

Burlington, Stowe, Cabot Farmers' Store, Vermont State House, Magic Hat Brewing Company
Highlights from your plan
Shelburne Museum ©
Shelburne Museum
Shelburne Farms ©
Shelburne Farms
Stowe Recreation Path ©
Stowe Recreation Path

3
nights
Saint Johnsbury

Saint Johnsbury ©
St. Get out of town with these interesting Saint Johnsbury side-trips: Museum of Everyday Life (in Glover), Barre (Hope Cemetery & Rock of Ages Granite Quarry) and Montpelier (Morse Farm Maple Sugarworks & Bragg Farm Sugar House & Gift Shop). The adventure continues: stroll around Dog Mountain Home of Stephen Huneck Gallery, contemplate the waterfront views at Lake Willoughby, see the interesting displays at Fairbanks Museum and Planetarium, and stroll through Lamoille Valley Rail Trail.

To see maps, more things to do, reviews, and more tourist information, you can read our Saint Johnsbury trip builder tool .

Drive from Shelburne to Saint Johnsbury in 2 hours. In October, daily temperatures in Saint Johnsbury can reach 60°F, while at night they dip to 40°F. Finish your sightseeing early on the 11th (Fri) to allow enough time to drive to Woodstock.

Things to do in Saint Johnsbury

Parks Nature Museums

Side Trips

Barre, Montpelier, Museum of Everyday Life, Lake Willoughby
Highlights from your plan
Fairbanks Museum and Planetarium ©
Fairbanks Museum and Planetarium
Morse Farm Maple Sugarworks ©
Morse Farm Maple Sugarworks

6
nights
Woodstock

Woodstock ©
Woodstock is the shire town of Windsor County, Vermont, United States. Venture out of the city with trips to Killington Resort (in Killington) and Bennington (The Old First Church, Bennington Battle Monument, & more). The adventure continues: experience rural life at Sugarbush Farm, explore the activities along Ottaquechee River, take in the awesome beauty at Mount Tom, and explore the wealth of natural beauty at Marsh - Billings - Rockefeller National Historical Park.

To find photos, more things to do, where to stay, and more tourist information, go to the Woodstock trip planner .

Getting from Saint Johnsbury to Woodstock by car takes about 1.5 hours. October in Woodstock sees daily highs of 62°F and lows of 40°F at night. Wrap up your sightseeing on the 17th (Thu) early enough to drive to Brattleboro.

Things to do in Woodstock

Parks Nature Historic Sites

Side Trips

Quechee, Bennington, Windsor, Eshqua Bog Natural Area, Killington Resort
Highlights from your plan
Sugarbush Farm ©
Sugarbush Farm
Billings Farm & Museum ©
Billings Farm & Museum

5
nights
Brattleboro

Brattleboro ©
Brattleboro, originally Brattleborough, is a town in Windham County, Vermont, United States. Explore the numerous day-trip ideas around Brattleboro: Dover (Mount Snow Resort & Skyline Overlook), Vermont Shepherd (in Putney) and Molly Stark State Park (in Marlboro). There's still lots to do: relax in the rural setting at Robb Family Farm, tour the pleasant surroundings at Retreat Trails, walk around Living Memorial Park, and browse the eclectic array of goods at Brattleboro Farmers' Market.

For more things to do, maps, ratings, and tourist information, you can read our Brattleboro trip planning tool .

You can drive from Woodstock to Brattleboro in 1.5 hours. In October in Brattleboro, expect temperatures between 62°F during the day and 40°F at night. Wrap up your sightseeing on the 22nd (Tue) to allow time to drive to Manchester.

Things to do in Brattleboro

Parks Trails Outdoors

Side Trips

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

5
nights
Manchester

Manchester ©
Manchester is a town in, and one of two shire towns (county seats) of, Bennington County, Vermont, United States. Venture out of the city with trips to Whiting Library (in Chester), Grafton (Jud Hartmann Gallery & Gallery North Star) and Londonderry (TimberQuest Park & Lowell Lake State Park). And it doesn't end there: explore and take pictures at Hildene, The Lincoln Family Home, view the masterpieces at Southern Vermont Arts Center, relax in the rural setting at Mad Tom Orchard, and witness the site of a historic battle at Hubbardton Battlefield.

To find where to stay, photos, other places to visit, and other tourist information, you can read our Manchester day trip planning app .

Traveling by car from Brattleboro to Manchester takes 1.5 hours. In October, daytime highs in Manchester are 62°F, while nighttime lows are 41°F. Finish your sightseeing early on the 27th (Sun) so you can travel back home.

Things to do in Manchester

Parks Nature Museums

Side Trips

Weston, Londonderry, Grafton, Arlington, Jamaica State Park
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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