72 Hours in Bennington
Two nights and
Three Days in Bennington
The state’s first town and the gateway to southern Vermont, Bennington abounds with history and culture. This shire town is everything you imagine Vermont to be, from the classic Main Street with locally owned shops to the stunning architecture.
A classic town with a modern flair, Bennington boasts a lively community of outdoor enthusiasts, entrepreneurs and artists, world-class golf and some of the state’s most iconic historic sites. Spend a weekend exploring Bennington and uncover the story of Vermont’s beginnings.
Visit At a Glance
These three days offer suggestions for things to do surrounding lodging, dining, shopping, and nearby attractions. Use this itinerary as a guide for further discovery – bookmark these locations and walk the downtown. Another great way to find a hidden gem is to ask a shop owner for their favorite local spot.
Key Points of Interest
Each day is comprised of shops, restaurants, and cultural attractions.
- Day 1: Start at the southern end of Bennington and explore the shops, restaurants, and culture that this lively downtown area has to offer.
- Day 2: Discover the history and culture that influenced the town’s past and informs the Bennington of today.
- Day 3: Spend the day taking in the sights of the classic New England villages that make up Bennington and learn the town’s connection to one of America’s great poets.
Start at the southern end of Bennington and explore the shops, restaurants, and culture that this lively downtown area has to offer.
– DAY 1
HAWKINS HOUSE
A second-generation, family-owned contemporary crafts gallery and shop with artisans from around Vermont and across the nation and the world.
Bennington Performing Arts Center/Oldcastle Theatre Company
Home to Oldcastle Theater Company, BPAC is Bennington’s cultural cornerstone. View the calendar to see what’s playing during your visit.
Village Chocolate Shoppe
Explore the world of chocolate, learning the history, where it comes from and how it is made. Shop the assortment of homemade chocolate and candy.
MADISON BREWING COMPANY
Stop in to the area’s first brew pub for a craft beer and mouth-watering food. Their family-friendly menu offers something to satisfy everyone’s cravings.
SOUTH SHIRE INN
This 1887 Queen Ann style Victorian inn provides the perfect starting point for your adventures. Enjoy a full breakfast before setting off to explore Bennington.
Discover the history and culture that influenced the town’s past and informs the Bennington of today.
– DAY 2
BENNINGTON MUSEUM
Explore the rich history of Vermont through curated exhibits of art and history, from the 18th century to present day.
OLD FIRST CONGREGATIONAL CHURCH
A short walk from Bennington Museum, stop in for a tour (offered May – October) and learn the history of the building, originally constructed in 1805, and its influence on the town.
THE GRILLE
Stop in for lunch or dinner after a round of golf at Mount Anthony Country club. Take in the views of the Green Mountains and enjoy the fresh and delicious seasonal menus influenced by local ingredients.
THE FOUR CHIMNEYS INN
Relax at this picturesque Vermont bed and breakfast in the historic neighborhood of Old Bennington. Enjoy the old-world grandeur and modern amenities.
MOUNT ANTHONY COUNTRY CLUB
This championship rated golf course offers sweeping views of the Green Mountains and is guaranteed to challenge players of every level.
Bennington Battle Monument
One of Vermont’s most prominent historic sites, this monument commemorates a pivotal victory at the Battle of Bennington. Explore the ground-level exhibits and climb the steps to the observation deck to take in the views of three states.
Spend the day taking in the sights of the classic New England villages that make up Bennington and learn the town’s connection to one of America’s great poets.
– DAY 3
SILK ROAD COVERED BRIDGE AND BURT HENRY COVERED BRIDGE
No trip to Vermont is complete without visiting one, or two, of the state’s iconic covered bridges. These two bridges, built in 1840, cross the Walloomsac River and are listed on the National Register of Historic Places.
PARK-MCCULLOUGH HISTORIC HOUSE
Open seasonally, this Victorian Mansion is one of the best preserved and most significant mansions in New England. Enjoy programming and events on the property and take in New England life, from the 1770’s to present day.
ROBERT FROST STONE HOUSE MUSEUM
Located at Bennington College, this literary landmark is located only minutes away from Frost’s gravesite in Old Bennington. Frost resided in the house from 1920 to 1929, which guests can visit and learn more about Frost’s literature and poetry.
PANGEA RESTAURANT
Offering a unique dining experience, Pangea is the perfect place to cap off your Bennington adventure. The French-influenced menu features quality local ingredients and offers fine-dining options on weekends.
HAMPTON INN BENNINGTON
Located minutes from outdoor adventures, world-class shopping, fine dining, arts and crafts, historical museums and covered bridges. Enjoy the free hot breakfast and indoor pool and sauna.
ROBERT FROST TRAILHEAD
Explore the two-mile path through the woods on the farmland once owned by Frost. Stop mid-way on the footbridge to enjoy the views of Paran Creek and continue on to the vantage point to look out over North Bennington.
About the Vermont Inspiration Guide
This itinerary comes from the Vermont Inspiration Guide through a partnership between the Vermont Department of Tourism and Marketing and the Vermont Chamber of Commerce. This free annual publication highlights Vermont’s restaurants, retailers, attractions, and outdoor adventures and can be ordered online along with other trip planning resources.