Call it quirky, and be sure to call ahead, when planning a visit to wacky and wonderful Waitsfield, Vermont.
Vermont’s oldest operating covered bridge crosses the Mad River in historic Waitsfield, a perfectly picturesque New England town of charming nineteenth-century clapboard buildings. But beneath that quaint exterior runs a cutting-edge current that has spawned several artistic ventures, creating a quirky clash of old and new.
A haven for skiers who prefer the unadulterated terrain of Sugarbush Resort and member-owned Mad River Glen, the Mad River Valley—with Waitsfield at its core—nurtures locals and transplants who march to the beat of their own drum. That sometimes means places won’t be open when expected or keep inconsistent off-season hours. The bottom line: before you wander to Waitsfield to see something specific, call ahead.
June Anderson equates Waitsfield’s sensibility with the defiant “ski it if you can” motto of Mad River Glen. “In the Mad River, you have to be willing to reach a little farther and work a little harder, but the reward is a little richer and a little sweeter.”
Anderson and her husband, Wendell, own the Bundy Modern, a boxy minimalist structure fronted by floor-to-ceiling windows—distinctly out of place in the sloping terrain—which serves as a contemporary art gallery and their home. It hosts exhibitions mostly in the summer; in the winter, she says, skiers tend to drive up late on Friday, hit the runs all weekend and go home without doing much else.
The Madsonian Museum of Industrial Design contrasts such modernity with a whimsical assembly of old motorcycles, gumball machines, toys, typewriters, telephones (with dials!), and other commercial creations of a former era. In the center of the Waitsfield Village Historic District, it’s open Friday through Sunday and by appointment.
Less dusty and open all year, the Big Picture Theater and Café merges a vintage movie house and tavern with an innovative, locally inspired menu that’s hardly an afterthought to the cinematic fare. Filmgoers can enjoy dishes such as fried chicken, tofu satay, and homemade desserts—including the famous Very Small Donuts— in the theater while they watch.
Back in the historic village, there’s an unexpected oasis of high fashion. 4orty Bridge Boutique features a well-curated collection of clothing and accessories made mostly by U.S. designers, including jewelry handmade by the shop’s owner. It’s one of those sophisticated surprises that pop up in Waitsfield and make it so incongruously appealing.