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

Middlebury is the shire town (county seat) of Addison County, Vermont, United States. Vermont Marble Museum and Lincoln Peak Vineyard are good opportunities to explore the local culture. Step out of the city life by going to Warren Falls and Texas Falls Recreation Area. You'll find plenty of places to visit near Middlebury: Brandon Music (in Brandon), New England Maple Museum (in Pittsford) and Baird Farm Vermont Maple Syrup (in Chittenden). The adventure continues: see the interesting displays at Lake Champlain Maritime Museum, hike along Robert Frost Wayside Trail, sample the tasty concoctions at Otter Creek Brewing, and enjoy the sand and surf at D.A.R. State Park.
To see ratings, traveler tips, where to stay, and tourist information, use the Middlebury tour builder 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. When traveling from Vancouver in September, plan for a bit warmer days in Middlebury, with highs around 26°C, while nights are about the same with lows around 12°C. Finish your sightseeing early on the 6th (Wed) so you can drive to Bennington.
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To see ratings, traveler tips, where to stay, and tourist information, use the Middlebury tour builder 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. When traveling from Vancouver in September, plan for a bit warmer days in Middlebury, with highs around 26°C, while nights are about the same with lows around 12°C. Finish your sightseeing early on the 6th (Wed) so you can drive to Bennington.
Side Trips
Vergennes, Half Moon State Park, Woodchuck Cider House, New England Maple Museum, Baird Farm Vermont Maple Syrup
Find places to stay Sep 1 — 6:
Highlights from your trip
Bennington — 7 nights
Bennington is a town in Bennington County, Vermont, in the United States. 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 Woodford State Park. Explore the numerous day-trip ideas around Bennington: Emerald Lake State Park (in Dorset), Honora Winery & Vineyard (in Jacksonville) and Manchester (Hildene, The Lincoln Family Home, Lye Brook Falls, &more). There's lots more to do: take in the views from Silk Road Covered Bridge, stroll the grounds of New Catholic Cemetery, explore the world behind art at Brattleboro Museum & Art Center, and look for gifts at Manchester Hot Glass.
To find where to stay, other places to visit, photos, and tourist information, read our Bennington trip planner.
Traveling by car from Middlebury to Bennington takes 2 hours. Expect a daytime high around 27°C in September, and nighttime lows around 10°C. Finish your sightseeing early on the 13th (Wed) to allow enough time to drive to Woodstock.
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To find where to stay, other places to visit, photos, and tourist information, read our Bennington trip planner.
Traveling by car from Middlebury to Bennington takes 2 hours. Expect a daytime high around 27°C in September, and nighttime lows around 10°C. Finish your sightseeing early on the 13th (Wed) to allow enough time to drive to Woodstock.
Side Trips
Find places to stay Sep 6 — 13:
Highlights from your trip
Woodstock — 5 nights

Woodstock is the shire town of Windsor County, Vermont, United States. Discover out-of-the-way places like President Calvin Coolidge State Historic Site and Calvin Coolidge Homestead. American Precision Museum 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). Next up on the itinerary: take your sightseeing to a higher altitude at Mount Tom, tour the pleasant surroundings at Thundering Brook Falls Trail, contemplate the waterfront views at Ottaquechee River, and admire the majestic nature at Quechee State Park.
For maps, where to stay, more things to do, and more tourist information, you can read our Woodstock itinerary planner.
Traveling by car from Bennington to Woodstock takes 2 hours. Alternatively, you can take a bus. In September, daytime highs in Woodstock are 28°C, while nighttime lows are 11°C. Cap off your sightseeing on the 18th (Mon) early enough to go by car to Saint Johnsbury.
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For maps, where to stay, more things to do, and more tourist information, you can read our Woodstock itinerary planner.
Traveling by car from Bennington to Woodstock takes 2 hours. Alternatively, you can take a bus. In September, daytime highs in Woodstock are 28°C, while nighttime lows are 11°C. Cap off your sightseeing on the 18th (Mon) early enough to go by car to Saint Johnsbury.
Side Trips
Find places to stay Sep 13 — 18:
Highlights from your trip
Saint Johnsbury — 2 nights

St. 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. 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.
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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. 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
Find places to stay Sep 18 — 20:
Highlights from your trip
Stowe — 10 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.Get a sense of the local culture at Boyden Valley Winery & Spirits and Tea at the Governor's House. Eschew the tourist crowds and head to Toll Rd and Gold Brook Covered Bridge (Emily's Covered Bridge). Venture out of the city with trips to Smugglers' Notch Distillery - Maple Products - Gift Shop - Local Products (in Jeffersonville), Kill Kare State Park (in Saint Albans) and Alburg Dunes State Park (in Alburgh). The adventure continues: stroll around Elmore State Park, take your sightseeing to a higher altitude at Mount Mansfield State Forest, learn about winemaking at Fresh Tracks Farm Vineyard and Winery, and steep yourself in history at Ethan Allen Homestead.
Plan trip to Stowe with our itinerary maker to find out where to go and what to do.
Drive from Saint Johnsbury to Stowe in 1.5 hours. In September in Stowe, expect temperatures between 26°C during the day and 10°C at night. Finish your sightseeing early on the 30th (Sat) to allow enough time to fly back home.
Side Trips
Find places to stay Sep 20 — 30:
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.