30 days in Vermont Itinerary
Created using Inspirock Vermont trip itinerary planner
Start: Vancouver
Fly to Plattsburgh International Airport, Drive to Middlebury
1
Middlebury
— 5 nights
Drive
2
Bennington
— 7 nights
Drive
3
Woodstock
— 5 nights
Drive
4
Saint Johnsbury
— 2 nights
Drive
5
Stowe
— 10 nights
Fly
End: Vancouver
Fri, Sep 1 - Sat, Sep 30
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Middlebury — 5 nights

Vermont Marble Museum and Brandon Music are good opportunities to explore the local culture. Step out of the city life by going to Warren Falls and Button Bay State Park. You'll find plenty of places to visit near Middlebury: Baird Farm Vermont Maple Syrup (in Chittenden), New England Maple Museum (in Pittsford) and Mt. Philo State Park (in Charlotte).
To find traveler tips, ratings, other places to visit, and other tourist information, use the Middlebury trip planning app.
Vancouver, Canada to Middlebury is an approximately 18-hour combination of flight and car. You can also drive. The time zone difference when traveling from Vancouver to Middlebury is 3 hours. Traveling from Vancouver in September, you will find days in Middlebury are a bit warmer (26°C), and nights are about the same (12°C). Wrap up your sightseeing on the 6th (Wed) early enough to drive to Bennington.
more
To find traveler tips, ratings, other places to visit, and other tourist information, use the Middlebury trip planning app.
Vancouver, Canada to Middlebury is an approximately 18-hour combination of flight and car. You can also drive. The time zone difference when traveling from Vancouver to Middlebury is 3 hours. Traveling from Vancouver in September, you will find days in Middlebury are a bit warmer (26°C), and nights are about the same (12°C). Wrap up your sightseeing on the 6th (Wed) early enough to drive to Bennington.
Side Trips
Highlights from your trip
Bennington — 7 nights
Explore hidden gems such as The Old First Church and Equinox Preservation Trust. Step out of the city life by going to Equinox Mountain and Lye Brook Falls. Explore the numerous day-trip ideas around Bennington: Emerald Lake State Park (in Dorset), Manchester (Hildene, The Lincoln Family Home & Southern Vermont Arts Center) and Honora Winery & Vineyard (in Jacksonville).
To find where to stay, ratings, photos, and more tourist information, read Bennington trip planner.
Getting from Middlebury to Bennington by car takes about 2 hours. In September, daily temperatures in Bennington can reach 27°C, while at night they dip to 10°C. Cap off your sightseeing on the 13th (Wed) early enough to go by car to Woodstock.
more
To find where to stay, ratings, photos, and more tourist information, read Bennington trip planner.
Getting from Middlebury to Bennington by car takes about 2 hours. In September, daily temperatures in Bennington can reach 27°C, while at night they dip to 10°C. Cap off your sightseeing on the 13th (Wed) early enough to go by car to Woodstock.
Side Trips
Highlights from your trip
Woodstock — 5 nights

Discover out-of-the-way places like President Calvin Coolidge State Historic Site and Taftsville Covered Bridge. Calvin Coolidge Homestead and Vermont Toy Museum are good opportunities to explore the local culture. Explore the numerous day-trip ideas around Woodstock: Ludlow (Buttermilk Falls & Healdville Trail).
To see maps, traveler tips, where to stay, and tourist information, read Woodstock road trip planning tool.
You can drive from Bennington to Woodstock in 2 hours. Another option is to take a bus. In September, daily temperatures in Woodstock can reach 28°C, while at night they dip to 11°C. Finish up your sightseeing early on the 18th (Mon) so you can go by car to Saint Johnsbury.
more
To see maps, traveler tips, where to stay, and tourist information, read Woodstock road trip planning tool.
You can drive from Bennington to Woodstock in 2 hours. Another option is to take a bus. In September, daily temperatures in Woodstock can reach 28°C, while at night they dip to 11°C. Finish up your sightseeing early on the 18th (Mon) so you can go by car to Saint Johnsbury.
Side Trips
Highlights from your trip
Saint Johnsbury — 2 nights

On the 19th (Tue), get a new perspective on nature at Fairbanks Museum and Planetarium, then admire the masterpieces at St. Johnsbury Athenaeum, and then admire the majestic nature at Maidstone State Park. Keep things going the next day: take in the awesome beauty at Mount Pisgah, contemplate the waterfront views at Lake Willoughby, and then see the interesting displays at Bread and Puppet Theater.
To see ratings, maps, other places to visit, and more tourist information, read Saint Johnsbury tour planner.
You can drive from Woodstock to Saint Johnsbury in 1.5 hours. Alternatively, you can drive. In September in Saint Johnsbury, expect temperatures between 26°C during the day and 11°C at night. Finish your sightseeing early on the 20th (Wed) so you can drive to Stowe.
more
To see ratings, maps, other places to visit, and more tourist information, read Saint Johnsbury tour planner.
You can drive from Woodstock to Saint Johnsbury in 1.5 hours. Alternatively, you can drive. In September in Saint Johnsbury, expect temperatures between 26°C during the day and 11°C at night. Finish your sightseeing early on the 20th (Wed) so you can drive to Stowe.
Side Trips
Highlights from your trip
Stowe — 10 nights

The Ski Capital of the East
Get a sense of the local culture at Hope Cemetery and Fresh Tracks Farm Vineyard and Winery. Eschew the tourist crowds and head to Toll Rd and Boyden Valley Winery & Spirits. Venture out of the city with trips to Kill Kare State Park (in Saint Albans), Smugglers' Notch Distillery - Maple Products - Gift Shop - Local Products (in Jeffersonville) and Alburg Dunes State Park (in Alburgh). And it doesn't end there: walk around Elmore State Park, sample some tasty brews at a beer tour and tasting, hike along Burlington Bike Path, and take in breathtaking views at Sterling Falls Gorge.
To see where to stay, traveler tips, maps, and more tourist information, you can read our Stowe travel planner.
Drive from Saint Johnsbury to Stowe in 1.5 hours. Expect a daytime high around 26°C in September, and nighttime lows around 10°C. Finish up your sightseeing early on the 30th (Sat) so you can catch the flight back home.
more
To see where to stay, traveler tips, maps, and more tourist information, you can read our Stowe travel planner.
Drive from Saint Johnsbury to Stowe in 1.5 hours. Expect a daytime high around 26°C in September, and nighttime lows around 10°C. Finish up your sightseeing early on the 30th (Sat) so you can catch the flight back home.
Side Trips
Highlights from your trip
Vermont travel guide
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.