48 Hours in Bennington, VT

This recommended itinerary highlights local points of interest and reveals the active, indulgent, and creative character of the locale. You will find breathtaking scenery, inspiration, live music, historical significance, fresh air, and good food around every corner. The running theme, we are proud to say, is delicious donuts! 

Day 1, 2:00 pm: A Downtown Ramble

Shake off the car ride with a walk downtown, which offers opportunities to taste locally made beverages and browse fun shops, including The Bennington Bookshop, alumni-owned Fiddlehead at Four Corners, and The Village Chocolate Shoppe. Grab some unique dorm decor at one of several downtown antique shops, and if you’re in the mood for Vermont-made specialties, try Bringing You Vermont. 

4:00 pm: Winding Through Wildflowers

Stroll through the Bennington Museum’s George Aiken Wildflower Trail, a large annotated woodland garden that showcases the many native plants that Aiken (a two-term governor and six-term U.S. Senator) loved, propagated, and wrote about in his book, Pioneering with Wildflowers. 

5:00 pm: Music at the Museum

The Bennington Museum also offers free concerts 5:00-7:00 pm every Friday through September 8. The series features bands from a wide range of musical genres, kids’ activities, and free food from Mexican street food restaurant The Avocado Pit. 

7:00 pm: A Creemee and a Movie

At Billy T’s Northside Dairy Bar you can have what is often called “the quintessential Vermont experience” and “essential summer fare”: a maple creemee. (Vermont Governor Phil Scott sometimes recommends residents get a maple creemee in times of stress, but you can have one for fun too.) 

Then head the short distance to Bennington Cinemas, which offers new releases for just $8.50 and popcorn buttered with Vermont’s finest Cabot butter. Or wait a little later to catch a double feature on the biggest of the big screens: Hathaway’s Drive-In Theatre in nearby North Hoosick, NY. 

Day 2, 9:00 am: The Scenic Route to the Blue Benn Diner

Drive from North Bennington to Bennington via Silk Road to go over one of North Bennington’s three covered bridges. There’s a pull off to allow for one-lane travel, but it’s also great for parking while you take a practically mandatory photo. This route will also take you past the historic and majestic Bennington Battle Monument. 

Wake up to the deliciousness of a freshly grilled donut, a stack of blueberry almond pancakes, or one of many other signature dishes available at Bennington College alum-owned Blue Benn Diner. The classic 1957 “silk city” diner car, complete with a tiny jukebox at every table, attracts locals and visitors alike. The spot has been included in many food and travel magazines and rated in the top ten of diners nationwide. 

10:00 am: Nowhere More “New England”

Get a ride to the Robert Frost Stone House Museum at Bennington College, where U.S. Poet Laureate Robert Frost composed some of his most famous poems, including "Stopping by Woods on a Snowy Evening." The museum opens fresh conversations about the foundational elements of Frost’s life: poetry, farming, and teaching. 

12:00 pm: Fresh Air For All

Take the two-mile flat and gently sloping Robert Frost Trail directly from the Robert Frost Stone House parking lot to Lake Paran Recreation. You will find lots of natural beauty and several geocaches along the way. Lake Paran offers picnicking, swimming, boating, and a concession stand. A quick 20-minute walk from campus, this is a favorite place for Bennington College students to cool off.

4:00 pm: Art Around Town 

Then tour the North Bennington Outdoor Sculpture Show (NBOSS), now in its 26th year. From the show’s website, you can get a map of exhibits and hear audio clips from each artist describing their work. Sculptors include several Bennington College alumni. Open through November 11, 2023. 

7:00 pm: Pubbing it Up

After a hike, a swim, and the sculpture show, you will need some pubfare. Drop by Kevin’s in North Bennington. (The Kevin’s Burger is unbeatable. It could even become a recipe you replicate at home.) Best of all, this relaxed place is perfect for hanging out, meeting locals, and reliving the high points of the day. 

8:00 pm: Stargazing at the End of the World

Watch the stars come out one by one at Bennington College’s most picturesque spot, known as the End of the World. It’s at the southernmost end of the quad. 

Day 3, 9:00 am: Go Nuts for Donuts

Alumni-owned Prospect Coffee House is not to be missed. This North Bennington cafe features locally roasted Iron Coffee Co. coffee, teas from nearby Saratoga Tea & Honey, and a charming menu with European flair. Sunday mornings are for donuts, which are made fresh and sell fast! 

10:00 am: History and Hiking

Park-McCullough Historic Governor’s Mansion is one of the best-preserved Victorian mansions in New England. Architecturally significant, it represents its time, illustrates both local and Vermont history, and reveals the story of an enterprising family. Wonderful cultural and community events dot its calendar. Adjacent to the property is the Mile-Around Woods, a favorite local hiking spot, and walking in the fields nearby will give you the feeling of being in a 19th-century landscape painting. 

12:00: An Alfresco Lunch

Pop into alumni-owned Powers Market, one of the oldest and most iconic Vermont country stores, for the makings of a superb lunch. They have creative specials and delicious deli sandwiches made to order. Get some fresh berries, snacks, and beverages for a picnic and local honey and maple products as tasty souvenirs. While there, say “hi” to Clark, Official Shop Dog. A lovely riverside park around the corner is a great place to enjoy both your meal and the scenery.

2:00 pm: Culture and Agriculture

No visit to Southwestern Vermont would be complete without a stop at a farm or two. There are many to choose from. Depending on the season, you can pick-your-own blueberries at The Blueberry House, sample oodles of fresh produce and local cheeses at Clearbrook Farm, and commune with dromedaries at Shaftsbury Alpacas and the Alpaca Shack. And if you need more donuts for the ride home, The Apple Barn is the place to go.