31 days in Vermont Itinerary

31 days in Vermont Itinerary

Created using Inspirock Vermont visit planner

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Make it your trip
Fly
1
Manchester
— 5 nights
Drive
2
Brattleboro
— 5 nights
Drive
3
Woodstock
— 5 nights
Drive
4
Middlebury
— 5 nights
Drive
5
Saint Johnsbury
— 3 nights
Drive
6
Stowe
— 7 nights
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Manchester

— 5 nights
Manchester is a town in, and one of two shire towns (county seats) of, Bennington County, Vermont, United States. You'll explore the less-touristy side of things at The Old First Church and Equinox Preservation Trust. Get out of town with these interesting Manchester side-trips: Weston Priory (in Weston) and Bennington (The Bennington Center for the Arts, New Catholic Cemetery, &more). There's much more to do: take in the dramatic scenery at Lye Brook Falls, experience rural life at North Meadow Farm, shop like a local with Norman Rockwell Exhibition, and take your sightseeing to a higher altitude at Equinox Mountain.

To find maps, photos, and more tourist information, go to the Manchester trip itinerary app.

Seattle to Manchester is an approximately 10-hour flight. You can also drive; or do a combination of train and bus. Due to the time zone difference, you'll lose 3 hours traveling from Seattle to Manchester. Traveling from Seattle in October, expect a bit cooler with lows of 41°F in Manchester. Finish up your sightseeing early on the 6th (Wed) so you can go by car to Brattleboro.

Things to do in Manchester

Parks · Museums · Shopping · Historic Sites

Side Trips

Brattleboro

— 5 nights
Brattleboro, originally Brattleborough, is a town in Windham County, Vermont, United States. Explore hidden gems such as Creamery Covered Bridge and Robb Family Farm. Explore the numerous day-trip ideas around Brattleboro: Molly Stark State Park (in Marlboro) and Wilmington (The Art of Humor Gallery, Serenity Spa, &more). There's lots more to do: hunt for treasures at Brattleboro Farmers' Market, look for gifts at Hogback Mountain Gift Shop, take an in-depth tour of Brattleboro Museum and Art Center, and take in the views from West Dummerston Covered Bridge.

Quickly create a custom-made itinerary for Brattleboro using our trip planner.

Getting from Manchester to Brattleboro by car takes about 1.5 hours. In October, daytime highs in Brattleboro are 62°F, while nighttime lows are 40°F. Cap off your sightseeing on the 11th (Mon) early enough to go by car to Woodstock.

Things to do in Brattleboro

Shopping · Parks · Museums · Nature

Side Trips

Woodstock

— 5 nights
Woodstock is the shire town of Windsor County, Vermont, United States. Eschew the tourist crowds and head to President Calvin Coolidge State Historic Site and Taftsville Covered Bridge. You'll find plenty of places to visit near Woodstock: Joseph Smith Birthplace Memorial (in South Royalton) and Pierce's Store (in Shrewsbury). The adventure continues: take in the views from Cornish-Windsor Bridge, explore the activities along Ottaquechee River, delve into the lush surroundings at Mount Tom, and contemplate the long history of Calvin Coolidge Homestead.

Find out how to plan Woodstock trip without stress by asking Inspirock to help create an itinerary.

Traveling by car from Brattleboro to Woodstock takes 1.5 hours. In October, daily temperatures in Woodstock can reach 62°F, while at night they dip to 40°F. Wrap up your sightseeing on the 16th (Sat) to allow time to drive to Middlebury.

Things to do in Woodstock

Parks · Nature · Museums · Shopping

Side Trips

Middlebury

— 5 nights
Middlebury is the shire town (county seat) of Addison County, Vermont, United States. Discover out-of-the-way places like UVM Morgan Horse Farm and Baird Farm Vermont Maple Syrup. Venture out of the city with trips to Warren Falls (in Warren), Vermont Marble Museum (in Proctor) and Shelburne Orchards (in Shelburne). There's lots more to do: take in the views from Pulp Mill Covered Bridge, immerse yourself in nature at Mt. Philo State Park, experience rural life at Dakin Farm, and trek along Robert Frost Wayside Trail.

To find more things to do, photos, reviews, and other tourist information, refer to the Middlebury trip itinerary planner.

You can drive from Woodstock to Middlebury in 1.5 hours. In October in Middlebury, expect temperatures between 61°F during the day and 42°F at night. Wrap up your sightseeing on the 21st (Thu) early enough to travel to Saint Johnsbury.

Things to do in Middlebury

Parks · Outdoors · Nature · Museums

Side Trips

Saint Johnsbury

— 3 nights
St. You'll explore the less-touristy side of things at Dog Mountain Home of Stephen Huneck Gallery and Bread and Puppet Theater. Venture out of the city with trips to Lake Memphremagog (in Newport), East Burke (Mount Pisgah & Lake Willoughby) and Hill Farmstead Brewery (in Greensboro Bend). Next up on the itinerary: admire the masterpieces at St. Johnsbury Athenaeum, learn more about the world around you at Fairbanks Museum and Planetarium, and admire the landmark architecture of The Dog Chapel.

Planning Saint Johnsbury trip won't be overwhelming when you use Inspirock's itinerary maker.

Traveling by car from Middlebury to Saint Johnsbury takes 2.5 hours. Expect a daytime high around 60°F in October, and nighttime lows around 40°F. Wrap up your sightseeing on the 24th (Sun) to allow time to drive to Stowe.

Things to do in Saint Johnsbury

Parks · Nature · Museums · Breweries & Distilleries

Side Trips

Stowe

— 7 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.
Eschew the tourist crowds and head to Hope Cemetery and Gold Brook Covered Bridge (Emily's Covered Bridge). Venture out of the city with trips to Boyden Valley Winery & Spirits (in Cambridge), Montpelier (Camel's Hump, Vermont Historical Society Museum, &more) and Smugglers' Notch Distillery - Maple Products - Gift Shop - Local Products (in Jeffersonville). The adventure continues: cruise along Toll Rd, get a taste of the local shopping with Burlington Farmers Market, explore the stunning scenery at Sterling Falls Gorge, and get outside with Bingham Falls.

For ratings, reviews, and other tourist information, use the Stowe driving holiday planner.

Traveling by car from Saint Johnsbury to Stowe takes 1.5 hours. Expect a daytime high around 60°F in October, and nighttime lows around 39°F. Finish your sightseeing early on the 31st (Sun) to allow enough time to fly back home.

Things to do in Stowe

Parks · Breweries & Distilleries · Nature · Outdoors

Side Trips

Vermont travel guide

4.5
Gift & Specialty Shops · Ski Areas · Hiking Trails
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.