Bennington, Vermont | Could You Live Here?

The plates are singing like magpies at the Blue Benn Diner, a shiny bullet-shaped time capsule in Bennington, Vermont, that’s been around since 1948. Awash in pancakes and nostalgia, we’re flipping through the booth’s mini-jukebox, two songs for a quarter. “It’s a 60-year-old machine, kinda picky,” our server warns. I slide in a coin. Press the buttons: G2 (“Woodstock”) and J7 (“Leaving on a Jet Plane”). Soft and tinny, Crosby Stills Nash & Young fills the booth. This diner is “the place where the farmers and the lawyers go, a community place,” we’ve been told. It’s homey, like visiting a great-aunt who can’t stop cooking. But New England’s always been great for stirring nostalgia—sink a shovel into the earth and you’ll turn over a chunk of history. Some long-ago dweller walked this path, tilled this soil, moved that rock. We’re always stepping where someone stepped before.

In Bennington, the odds of that happening seem greater. Partly because it’s the largest town in southern Vermont: 42.5 square miles peppered with 15,700 folks. Partly because it’s rich in history: we’re on Ethan Allen and Green Mountain Boys turf, and lest we forget, the Bennington Battle Monument points a solemn finger skyward, marking Revolutionary War victory. It fits that the only museum dedicated to the preservation of covered bridges found a home at Bennington’s Center for the Arts.

Artists have overrun this landscape, too, spilling out of Bennington College or following in the footsteps of local icons like Robert Frost. The nation’s crusty poet laureate and four-time Pulitzer Prize winner is buried in the starkly beautiful cemetery behind Old First Church in Old Bennington. He shares a quiet spot with his wife and several of their children. The stone reads: “I had a lover’s quarrel with the world.” And the Bennington woods beyond are lovely, dark, and deep.

The Setting On the western edge of Green Mountain National Forest, a trio of Benningtons sit clustered near the New York border. Old, North, and just plain Bennington—their personalities are as different as any siblings’. And while outsiders may not distinguish, locals clearly do, says John Shannahan, director of Better Bennington, who “came for a weekend visit in 1982, and knew this is where I had to be.”

Downtown Bennington’s chunky Greek Revivals and jumble of artsy shops and cafés have a jittery Beat-poet buzz, spiced up with some highly regarded nearby museums, including the Bennington Museum, with its Grandma Moses collection. The town center is neatly quartered by Main (Route 9) and North streets (U.S. Route 7), leading to Old and North Bennington, respectively.

Old Bennington is an imposing enclave of Colonial homes, anchored by the 306-foot Bennington Battle Monument and Old First Church. If Bennington rubs against you like a raucous puppy, Old Bennington is the retired Pomeranian show dog. North Bennington draws artists and Bennington College professors, its hub dominated by Powers Market (since 1833) and Pangaea, a lovely rustic-chic eatery. “North Bennington is the conscience of Bennington,” sums up Joey Kulkin, the colorful manager of Fiddlehead at Four Corners art gallery in Bennington. Social Scene It’s a cinch to meet interesting people, but it’s probably easier with a paintbrush in hand. If you’re creative, Bennington is the place to be, says Jana Lillie, director of operations at the 20-year-old Bennington Center for the Arts. “It’s easier to survive here as an artist. No one asks, ‘Oh, what else do you do?’” The Vermont Arts Exchange even offers low-rent housing for artists, in repurposed spaces.

And if the arts aren’t your thing but community spirit is, consider the Penguin Plunge, the chilly centerpiece of North Bennington’s Winterfest. The February dash into frigid Lake Paran benefits Special Olympics. “We cut the hole yesterday,” a volunteer tells me. “It’s probably 34 degrees,” he grins, as Team Lingerie pounds by, dressed in frilly pink. The burst of small-town spirit warms us all. Shopping Fiddlehead at Four Corners sits temptingly at the bull’s-eye center of Bennington. This elegant converted bank, reimagined by Joel and Nina Lentzner, who met at Bennington College, houses an insanely attractive fine-arts gallery, presided over by Joey Kulkin, whose wild hair and khaki shorts defy winter. Surrounded by proof, he declares: “This town is artistic—we have the college, theater, art, at the core of it all.”

Bennington Potters can deplete the remainder of your bank account, with loads of home furnishings besides its famous pottery, all tucked into an atmospheric old mill. And Jay’s Art Shop & Frame Gallery is the largest art-supply store in Vermont, presided over by “the original Jay-Z,” says Jay Zwynenburg, 82, who bought the circa-1865 former Drysdale department store building in 1987. He knows its history like an old friend: “The man who built it made his fortune during the Gold Rush. The counter is from the days when they were still cutting redwoods.”

Eating Out For starters, Blue Benn for blueberry–almond pancakes and local cheer; South Street Café for a hot cappuccino, Sunday-brunch jazz, and mile-high steamy windows. For a slice of NYC, Pangaea, with its herb crusts, beurre blanc, and pan-seared anything. Plus a divine bakery: Bakkerij Krijnen. Real Estate Size up the three personalities (Bennington, Old, and North) to see what appeals most. At the time of our visit, prices ranged wildly, from a charming 1930 updated bungalow in the heart of North Bennington Village, with separate studio/workshop, for $167,500, to the elegant 1779 Captain Nodiah Swift House, a 15-room Colonial on the village green in Old Bennington, for $579,000. In downtown Bennington, you could move into an 18th-century three-bedroom home on Main Street for $169,000. This feature originally appeared in the January/February 2015 issue of Yankee.