Each time my family drives into Bennington, Vermont, it feels a little like coming home. Though I’ve never lived in this little town for more than a few days at a time on vacation, it strikes a deep, familiar chord with me. Perhaps arriving in Bennington feels like home to me because, as a boy growing up in the Bronx, I recall vividly my first discovery of the great American painter Anna Mary Robertson, better known as Grandma Moses, who lived and worked in Bennington. The gentle curves of the Green Mountains just outside of town provide a soothing natural backdrop to this historic place, and they are the very mountains that appear in Grandma Moses’s folk paintings, depicting rural life and seasonal rituals such as sugar-mapling and trick-or-treating. The interplay between the natural world and the art world is at the very heart of this short and totally manageable road trip.
DAY 1: BENNINGTON, VERMONT
Bennington offers a range of accommodations, but we’ve become fond of the family-friendly Knotty Pine Motel, which has a dog-friendly policy, a very attentive and helpful staff, and a lovely swing set and pool. We especially appreciate the big map of New England that hangs in the main office. My youngest daughter kept asking to go visit the map, and I was so pleased that she’d connected with New England, tracing her finger over my sister’s home in New Hampshire, the beaches of Falmouth and Nantucket where we’ve visited, and the charming little city of New Bedford. It was only later that I realized that my daughter was actually less interested in the map and much more interested in the bowl of Tootsie Rolls the motel proprietor kept on her desk. Oh, well. The map is still a sweet memory, even if the candy was sweeter.
In Bennington, the must-see for art lovers is the Bennington Museum and Grandma Moses Schoolhouse. Here, you can view a wide variety of art in a charming and manageable setting. The museum’s permanent collection includes fine art, furniture, and household items from Vermont’s history as well as strikingly modern work by contemporary Bennington artists. The rooms devoted to Grandma Moses (the largest public collection of the “primitive” artist’s work) offer you the chance to see the Green Mountains in Moses’s iconic paintings or rural life and then peek out the window and see the real thing. Unforgettable.
The adjoining one-room Grandma Moses Schoolhouse includes chalk-boards and antique schoolbooks, games, and dress-up clothes. If you’re traveling with kids, they may be more enthralled by the schoolhouse than the art, and that’s fine: Let them go. They’ll remember how that schoolhouse made them feel long after they’ve forgotten your lectures on folk art.
In 1777, Bennington was the site of a major Revolutionary War battle, and each August, the town celebrates with a parade. Residents and visitors alike line the streets and cheer for the bands and marchers. We’ve been lucky enough to time our visits to parade weekend, and it is a nice way to meet the town’s year-round residents.
Don’t be fooled by the name. Kevin’s Sports Pub and Restaurant, in North Bennington, is much more than a place to watch a game on TV. We love its imaginative riffs on burgers, fish and chips, and other pub fare, and the local ales on tap offer a variety of vibrant flavors and textures.
In nearby South Shaftsbury, the Robert Frost Stone House Museum surprises, delights, and educates visitors with Frost’s famous poetry, such as “The Road Not Taken,” adorning the walls, with brief, easily digested lessons on his rhyme schemes and meter that even young kids will understand and appreciate. (If you’re headed for the Atlantic coast, drop by another Frost museum, his farmhouse in Derry, New Hampshire, on the way.)
Psst! Outside Bennington, there’s a hidden gem of a local lake whose name I promised not to publish because its modest snack bar and canoe rental business are really meant for locals. If you find yourself in conversation with a Bennington local, do ask about places to canoe. We had a family paddling adventure on the lake and down a nearby creek that we’ll never forget.
DAY 2: WILLIAMSTOWN, MASSACHUSETTS
Williamstown, just across the border into Massachusetts down U.S. 7, is another town where you can easily stay more than one night just to drink in all the art and natural beauty on display. The Clark Art Institute is home not only to a world-class permanent collection that includes European and American art from the Renaissance to the early 20th century (especially rich in work by American painters Winslow Homer, George Inness, and John Singer Sargent), but also to one of the finest museum snack bars I’ve ever experienced. For real. I recommend its salads and sandwiches, especially in good weather when you can eat out on a terrace. The museum’s grounds, including a children’s learning center, are a work of art themselves (they made Architectural Digest’s list of “buzz-worthy” museums). Williams College Museum of Art is another fine collection; focused on the college’s mission, the museum offers a broad range of pieces, from ancient Egyptian art to contemporary American and international work.
Williamstown Theatre Festival has been bringing acclaimed productions to the Berkshires each summer since 1955, another example of the exciting synergy between the natural world and human creativity that makes this region so special.
Williams Inn is a cozy place in the heart of Williamstown to rest your head in the Berkshires, having welcomed visitors since 1909. As with Bennington before it, you may want to stay more than one night to see all the sights.
DAY 3: NORTH ADAMS, MASSACHUSETTS
The cherry on top of your art lover’s road trip is the Massachusetts Museum of Contemporary Art (MASS MoCA), in North Adams. The nearby mountains and small-town vibe on the streets are a contrast to the hot, ultra-modern work you’ll encounter inside this restored 19th-century mill complex. The museum is an epicenter for the making of visual and performing arts, with residencies that bring cutting-edge creators to town. New exhibits of contemporary artists, including the museum’s Kidspace, are ongoing; check the museum’s excellent website, massmoca.org, for updates. When you’re ready to refuel, MASS MoCA’s Lickety Split lobby bistro is open during museum hours for breakfast and lunch (plus ice cream, espresso, fresh-squeezed lemonade, and, on show nights, a light dinner menu). The cute streets of North Adams also teem with international cuisine, funky cafés and coffee spots, and cool pubs.
Ready to hit the hay? The Porches Inn at MASS MoCA is self-consciously kitschy. (In keeping with the museum’s mission, the inn describes itself as “retro-edgy, industrial granny chic.”) You’ll enjoy closing your little hipster eyes in the imaginative heart of the Berkshires.
BOOK YOUR HOTEL WITH BUDGET TRAVEL
You can find and book a great hotel deal right at Budget Travel's Book a Hotel page.