32 days in Vermont Itinerary
Created using Inspirock Vermont route planner
Start: Chicago
Fly
1
Bennington
— 5 nights
Drive
2
Middlebury
— 6 nights
Drive
3
Woodstock
— 6 nights
Drive
4
Saint Johnsbury
— 5 nights
Drive
5
Stowe
— 9 nights
Fly
End: Chicago
Sat, Jul 1 - Tue, Aug 1
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View full calendar
Bennington — 5 nights
©
You'll find plenty of places to visit near Bennington: Manchester (Spa at Equinox, Hildene, The Lincoln Family Home, &more), Vermont Country Store (in Weston) and Jamaica State Park (in Jamaica).
To see ratings, where to stay, other places to visit, and more tourist information, read our Bennington tour site.
Chicago to Bennington is an approximately 3.5-hour flight. You can also drive; or do a combination of train and bus. Due to the time zone difference, you'll lose 1 hour traveling from Chicago to Bennington. Traveling from Chicago in July, expect a bit cooler with lows of 58°F in Bennington. Finish your sightseeing early on the 6th (Thu) to allow enough time to drive to Middlebury.
more
To see ratings, where to stay, other places to visit, and more tourist information, read our Bennington tour site.
Chicago to Bennington is an approximately 3.5-hour flight. You can also drive; or do a combination of train and bus. Due to the time zone difference, you'll lose 1 hour traveling from Chicago to Bennington. Traveling from Chicago in July, expect a bit cooler with lows of 58°F in Bennington. Finish your sightseeing early on the 6th (Thu) to allow enough time to drive to Middlebury.
Side Trips
Highlights from your trip
Middlebury — 6 nights
©
Change things up with these side-trips from Middlebury: New England Maple Museum (in Pittsford), Vermont Marble Museum (in Proctor) and Baird Farm Vermont Maple Syrup (in Chittenden).
To find maps, more things to do, reviews, and other tourist information, read our Middlebury trip itinerary tool.
Getting from Bennington to Middlebury by car takes about 2 hours. July in Middlebury sees daily highs of 80°F and lows of 60°F at night. Finish your sightseeing early on the 12th (Wed) to allow enough time to drive to Woodstock.
more
To find maps, more things to do, reviews, and other tourist information, read our Middlebury trip itinerary tool.
Getting from Bennington to Middlebury by car takes about 2 hours. July in Middlebury sees daily highs of 80°F and lows of 60°F at night. Finish your sightseeing early on the 12th (Wed) to allow enough time to drive to Woodstock.
Side Trips
Highlights from your trip
Woodstock — 6 nights
©
Woodstock is known for historic sites, nature, and sightseeing. Your trip includes some of its best attractions: relax in the rural setting at Sugarbush Farm, hike along Thundering Brook Falls Trail, explore the wealth of natural beauty at Marsh - Billings - Rockefeller National Historical Park, and look for all kinds of wild species at Vermont Institute of Natural Science (VINS).
To see photos, other places to visit, reviews, and tourist information, read our Woodstock attractions planner.
Getting from Middlebury to Woodstock by car takes about 1.5 hours. Other options: drive. In July, plan for daily highs up to 83°F, and evening lows to 59°F. Finish your sightseeing early on the 18th (Tue) to allow enough time to drive to Saint Johnsbury.
more
To see photos, other places to visit, reviews, and tourist information, read our Woodstock attractions planner.
Getting from Middlebury to Woodstock by car takes about 1.5 hours. Other options: drive. In July, plan for daily highs up to 83°F, and evening lows to 59°F. Finish your sightseeing early on the 18th (Tue) to allow enough time to drive to Saint Johnsbury.
Side Trips
Highlights from your trip
Saint Johnsbury — 5 nights
©
Explore the numerous day-trip ideas around Saint Johnsbury: Lake Memphremagog (in Newport), Old Stone House Museum (in Orleans) and Lake Willoughby (in East Burke).
To find reviews, maps, where to stay, and other tourist information, read our Saint Johnsbury tour itinerary app.
Traveling by car from Woodstock to Saint Johnsbury takes 1.5 hours. Alternatively, you can drive. In July, daytime highs in Saint Johnsbury are 79°F, while nighttime lows are 58°F. Cap off your sightseeing on the 23rd (Sun) early enough to go by car to Stowe.
more
To find reviews, maps, where to stay, and other tourist information, read our Saint Johnsbury tour itinerary app.
Traveling by car from Woodstock to Saint Johnsbury takes 1.5 hours. Alternatively, you can drive. In July, daytime highs in Saint Johnsbury are 79°F, while nighttime lows are 58°F. Cap off your sightseeing on the 23rd (Sun) early enough to go by car to Stowe.
Side Trips
Highlights from your trip
Stowe — 9 nights
©
The Ski Capital of the East
Change things up with these side-trips from Stowe: Burlington (Leddy Park, Burlington Bike Path, &more), Overlook Park (in South Burlington) and Montpelier (Morse Farm Maple Sugarworks & Hubbard Park). And it doesn't end there: trek along Stowe Recreation Path, steep yourself in history at Shelburne Farms, stroll through Trapp Family Lodge Outdoor Center, and explore the activities along Mad River.
To find reviews, traveler tips, and more tourist information, refer to the Stowe online sightseeing planner.
You can drive from Saint Johnsbury to Stowe in 1.5 hours. In July, plan for daily highs up to 79°F, and evening lows to 56°F. Finish your sightseeing early on the 1st (Tue) to allow enough time to fly back home.
more
To find reviews, traveler tips, and more tourist information, refer to the Stowe online sightseeing planner.
You can drive from Saint Johnsbury to Stowe in 1.5 hours. In July, plan for daily highs up to 79°F, and evening lows to 56°F. Finish your sightseeing early on the 1st (Tue) to allow enough time to fly 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.
