32 days in Vermont Itinerary

Bennington is a town in Bennington County, Vermont, in the United States. You'll find plenty of places to visit near Bennington: Manchester (Spa at Equinox, Hildene, The Lincoln Family Home, &more), Jamaica State Park (in Jamaica) and Vermont Country Store (in Weston). There's much more to do: take some stellar pictures from Bennington Battle Monument, take in the awesome beauty at Bromley Mountain, immerse yourself in nature at Woodford State Park, and take in the views from Silk Road Covered Bridge.

To find reviews, ratings, photos, and more tourist information, you can read our Bennington trip builder tool.

Chicago to Bennington is an approximately 3.5-hour flight. You can also drive; or do a combination of train and bus. The time zone changes from Central Standard Time (CST) to Eastern Standard Time (EST), which is usually a 1 hour difference. Expect little chillier evenings in Bennington when traveling from Chicago in July, with lows around 58°F. Finish up your sightseeing early on the 6th (Thu) so you can go by car to Middlebury.

Middlebury is the shire town (county seat) of Addison County, Vermont, United States. Change things up with these side-trips from Middlebury: Vermont Marble Museum (in Proctor), Baird Farm Vermont Maple Syrup (in Chittenden) and New England Maple Museum (in Pittsford). There's lots more to do: learn about winemaking at Lincoln Peak Vineyard, catch a live performance at Mahaney Center for the Arts, immerse yourself in nature at Allis State Park, and deepen your understanding at Middlebury College.

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

Traveling by car from Bennington to Middlebury takes 2 hours. July in Middlebury sees daily highs of 80°F and lows of 60°F at night. Wrap up your sightseeing on the 12th (Wed) to allow time to drive to Woodstock.

Woodstock is the shire town of Windsor County, Vermont, United States. Woodstock is known for historic sites, nature, and sightseeing. Your trip includes some of its best attractions: experience rural life at Sugarbush Farm, make a trip to Collective, the art of craft, contemplate the long history of Billings Farm & Museum, and take in the dramatic natural features at Quechee Gorge.

To see photos, ratings, and more tourist information, you can read our Woodstock planning app.

Traveling by car from Middlebury to Woodstock takes 1.5 hours. Alternatively, you can drive. Expect a daytime high around 83°F in July, and nighttime lows around 59°F. Wrap up your sightseeing on the 18th (Tue) early enough to drive to Saint Johnsbury.

St. Explore the numerous day-trip ideas around Saint Johnsbury: Lake Willoughby (in East Burke), Old Stone House Museum (in Orleans) and Lake Memphremagog (in Newport). The adventure continues: walk around Dog Mountain Home of Stephen Huneck Gallery, examine the collection at Bread and Puppet Theater, immerse yourself in nature at Maidstone State Park, and get curious at Museum of Everyday Life.

To find reviews, traveler tips, and more tourist information, go to the Saint Johnsbury trip itinerary builder tool.

Drive from Woodstock to Saint Johnsbury in 1.5 hours. Alternatively, you can drive. In July, plan for daily highs up to 79°F, and evening lows to 58°F. Wrap up your sightseeing on the 23rd (Sun) to allow time to drive to Stowe.

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.

Change things up with these side-trips from Stowe: Montpelier (Vermont State House, Morse Farm Maple Sugarworks, &more), Burlington (Leddy Park, Burlington Bike Path, &more) and Overlook Park (in South Burlington). 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.