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Your Bennington Bucket List: Top Attractions in Bennington Vermont

Getaway with a beautiful Vermont vacation this summer and experience all of our favorite Southern Vermont attractions. Stay 2, 3, 4 days or more. There is so much to do this time of year. Our Bennington Bucket List makes the planning easy so book your stay today and have fun checking off the list.

four chimneys inn exterior springtime Vermont sunny day
Day 1

  • Check into Four Chimneys Inn.
  • Settle in and relax with a cold cocktail on our stone patio overlooking the front lawn and gardens.
stone patio awning bistro chairs summer lowers
  • Stretch your legs with a walk through our historic Vermont village of Old Bennington. Stop off at Robert Frost’s Grave and stroll along the iconic New England fence of the Old First Church. Both are just a stone’s throw from the Four Chimneys Inn.
  • For dinner, head out to one of our favorite local restaurants. The Grille at Mount Anthony Country Club has tremendous views from their patio and friendly welcoming atmosphere.  Outdoor heaters make sure you have a comfortable outdoor dining option even on a chilly spring night. The Grille offers a wide range of menu selections including the most delicious Vermonter salad with a homemade maple balsamic and specials that range from Prime Rib to pastas to Avocado  toast featuring local Maplebrook Farms Burrata.   Upon checking in to the Four Chimneys, we will give an area guide with a great map, directions to The Grille along with a few more of our favorite recommendations in the area.
outdoor dining bennington vermont country club

Day 2

  • Start your day with a hearty breakfast  at your own private table at the Inn before exploring Bennington.
  • Take a trip back in time with a short walk to  The Bennington Museum. While, known for it’s extensive  Grandma Moses Exhibit, the whole museum is filled with 200 years of art, history and stories over the years.  Spend an hour or all afternoon. Either way, be sure to bring your gift-giving list because the gift shop is filled to the brim with lovely gifts made by Vermont artisans.
  • Head to Madison Brewing Company for a great burger and one of the area’s best micro brews. Or, if you feel like a picnic, grab a Boars Head deli sandwiches from the Elm Street Market or a burger and a shake from Billy T’s  Northside Dairy bar and take it to the Henry Bridge. What is more Vermont-y than a picnic by a covered bridge?
boy stepping-stones vermont covered bridge
  • After looping through the three covered bridges, starting with the Henry Bridge, check out the Bennington Battle Monument (open from May- October). Check out the first floor museum and take the elevator to the top for spectacular views. And don’t forget to check out the gift shop!
general stark statue bennington battle monument


  • Visit Bennington’s downtown and browse our one-of-a-kind shops including Hawkins House and Fiddlehead at Four Corners.  
  • Stop by Bennington Potters to view all of the beautiful handmade pottery. With 75 years of history, Bennington Potters is the largest hand-crafted potter in the United States. Before you leave take a tour of the factory and see how the pieces are made. Please note that Bennington Potters retail shop may be temporarily closed due to Covid, but does have a wonderful online selection (that you can have mailed to your house, or pick up in the Bennington store during your visit.)
stylish woman shopping at Bennington Potters
  • Head back to the Inn to get ready for another great dinner in Bennington. If you love Northern Italian check out Allegro Ristorante downtown. The spicy calamari is our favorite!


Day 3

  • Sleep in! But not too long as there is much to see and do!
  • After breakfast at the inn, head to North Bennington to the Park McCullough Historic Governor’s Mansion. We like this place so much, that we wrote a whole blog about the historic Vermont mansion! Take a tour of the mansion and then head down the street a mile or so to Mile Around Woods, a bucolic walking trail for all ages and abilities.
  • Just up the road from the Park McCullough Governor’s Mansion is the Shaftsbury Alpacas. Pet them, feed them and shop a collection of wonderful Alpaca hats, scarves and more.
alpaca mop-head haircut rustic barn

Day 4

  • Don’t forget breakfast!
  • Grab a picnic box lunch at Elm Street Market to take with you to
  • Hildene – The Lincoln Family Home! While there is no restaurant at Hildene, they have a lovely picnic spot to enjoy your sandwiches.
  • To get to Hildene, meander up the Shires Scenic Byway (7A). Tour the estate. Browse the amazing gift shop. Tour the fully restored Pullman train cars. Pet the goats and walk the trails.Hildene Estate The Lincoln Family Home exterior view with summer garden


  • Explore downtown Manchester, Vermont and all of the galleries and shops it has to offer.
  • Drop into the Southern Vermont Arts Center and help them celebrate more than 100 years of showing stunning art work.
  • Enjoy an early dinner in Manchester at Ye Olde Tavern for a classic New England experience or take the scenic drive back to try Pangaea Restaurant and Lounge in North Bennington! 



Plan your trip. See specials & packages offered at Four Chimneys Inn.