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 Lye Brook Falls. 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: stroll through Equinox Preservation Trust, 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 · Historic Sites · Museums · Shopping

Side Trips

Find places to stay Oct 1 — 6:
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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

Parks · Shopping · Museums · Nature

Side Trips

Find places to stay Oct 6 — 11:
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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 Calvin Coolidge Homestead. You'll find plenty of places to visit near Woodstock: Pierce's Store (in Shrewsbury) and Joseph Smith Birthplace Memorial (in South Royalton). The adventure continues: make a trip to Taftsville Covered Bridge, trek along Thundering Falls Trail, head outdoors with Outdoor Activities, and view the masterpieces at Simon Pearce Mill.

For other places to visit, more things to do, maps, and other tourist information, go to the Woodstock trip planner.

Drive from Brattleboro to Woodstock in 1.5 hours. In October, plan for daily highs up to 62°F, and evening lows to 40°F. Wrap up your sightseeing on the 16th (Sat) to allow time to drive to Middlebury.

Things to do in Woodstock

Parks · Museums · Nature · Shopping

Side Trips

Find places to stay Oct 11 — 16:
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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), Shelburne Orchards (in Shelburne) and Vermont Marble Museum (in Proctor). And it doesn't end there: head outdoors with Inn to Inn, trek along Robert Frost Wayside Trail, relax in the rural setting at Dakin Farm, and stop by Danforth Pewter.

To see more things to do, ratings, other places to visit, and more tourist information, read Middlebury tour itinerary planning website.

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. Finish your sightseeing early on the 21st (Thu) so you can travel to Saint Johnsbury.

Things to do in Middlebury

Parks · Outdoors · Nature · Museums

Side Trips

Find places to stay Oct 16 — 21:
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Saint Johnsbury

— 3 nights
St. You'll explore the less-touristy side of things at Dog Mountain Home of Stephen Huneck Gallery and St. Johnsbury Athenaeum. Venture out of the city with trips to Lake Memphremagog (in Newport), Hill Farmstead Brewery (in Greensboro Bend) and East Burke (Mount Pisgah & Lake Willoughby). And it doesn't end there: admire the striking features of The Dog Chapel, get a new perspective on nature at Fairbanks Museum and Planetarium, and examine the collection at Bread and Puppet Theater.

For traveler tips, where to stay, ratings, and other tourist information, go to the Saint Johnsbury attractions planning site.

Traveling by car from Middlebury to Saint Johnsbury takes 2.5 hours. In October in Saint Johnsbury, expect temperatures between 60°F during the day and 40°F at night. Wrap up your sightseeing on the 24th (Sun) to allow time to drive to Stowe.

Things to do in Saint Johnsbury

Parks · Museums · Nature · Breweries & Distilleries

Side Trips

Find places to stay Oct 21 — 24:
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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 Montpelier (Camel's Hump, Vermont Historical Society Museum, &more), Smugglers' Notch Distillery - Maple Products - Gift Shop - Local Products (in Jeffersonville) and Boyden Valley Winery & Spirits (in Cambridge). There's much more to do: get outside with Bingham Falls, look for gifts at Laughing Moon Chocolates, explore the activities along Lake Champlain, and explore the stunning scenery at Sterling Falls Gorge.

For traveler tips, other places to visit, photos, and other tourist information, you can read our Stowe trip itinerary planner.

Drive from Saint Johnsbury to Stowe in 1.5 hours. In October, daily temperatures in Stowe can reach 60°F, while at night they dip to 39°F. Wrap up your sightseeing on the 31st (Sun) early enough to fly back home.

Things to do in Stowe

Parks · Breweries & Distilleries · Nature · Outdoors

Side Trips

Find places to stay Oct 24 — 31:
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Vermont travel guide

4.5
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.