5 days in Vermont Itinerary

5 days in Vermont Itinerary

Created using Inspirock Vermont trip itinerary maker
Make it your trip
— 1 night
— 1 night
— 2 nights


Bennington — 1 night

Bennington is a town in Bennington County, Vermont, in the United States. Start off your visit on the 26th (Mon): admire the sheer force of Lye Brook Falls, take an in-depth tour of Hildene, The Lincoln Family Home, and then look for gifts at The Village Chocolate Shoppe. Keep things going the next day: contemplate in the serene atmosphere at The Old First Church, take some stellar pictures from Bennington Battle Monument, and then explore the different monuments and memorials at New Catholic Cemetery.

To find reviews, maps, ratings, and tourist information, read our Bennington day trip planner.

Louisville to Bennington is an approximately 5.5-hour flight. You can also drive; or do a combination of bus and train. Expect slightly colder temperatures when traveling from Louisville in September; daily highs in Bennington reach 74°F and lows reach 48°F. Finish up your sightseeing early on the 27th (Tue) so you can go by car to Woodstock.
Historic Sites · Museums · Parks · Nature
Side Trip

Woodstock — 1 night

Woodstock is the shire town of Windsor County, Vermont, United States. Start off your visit on the 28th (Wed): browse the exhibits of Billings Farm & Museum, then relax in the rural setting at Sugarbush Farm, then take in breathtaking views at Quechee Gorge, and finally snap pictures at Quechee Bridge.

For ratings, traveler tips, photos, and more tourist information, you can read our Woodstock day trip planning site.

You can drive from Bennington to Woodstock in 2 hours. Another option is to take a bus. In September, daytime highs in Woodstock are 75°F, while nighttime lows are 50°F. Finish up your sightseeing early on the 28th (Wed) so you can go by car to Stowe.
Museums · Parks · Nature · Historic Sites
Side Trip

Stowe — 2 nights

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.
Kick off your visit on the 29th (Thu): stroll through Stowe Recreation Path, hit the slopes at Stowe Mountain Resort, and then take in the awesome beauty at Mount Mansfield State Forest. Keep things going the next day: make a trip to Church Street Marketplace, then examine the collection at Shelburne Museum, and then tour the pleasant surroundings at Burlington Bike Path.

To find traveler tips, photos, reviews, and more tourist information, refer to the Stowe online travel planner.

Traveling by car from Woodstock to Stowe takes 1.5 hours. Alternatively, you can do a combination of taxi and train; or do a combination of bus and train. September in Stowe sees daily highs of 73°F and lows of 48°F at night. Finish your sightseeing early on the 30th (Fri) to allow enough time to fly back home.
Parks · Outdoors · Trails · Winter Sports
Side Trips

Vermont travel guide

Gift & Specialty Shops · Ski Areas · Historic Sites
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.