BENNINGTON, Vt. —
Bennington County calls itself the gateway to Vermont — and its past and future are both on full display.
In North Bennington, Robert Frost lived and wrote some of his most famous works, including “Stopping by Woods on a Snowy Evening.” “I think he loved living here,” said
Bennington Museum curator Jamie Franklin. “He certainly was very productive here.”
The museum tells the broader story of Vermont’s oldest county, from Revolutionary War artifacts tied to the Battle of Bennington to an unexpected relic of 1920s ambition: the Martin Wasp. Just 20 of the luxury cars were built in Bennington before the company folded in 1925.
The museum is also home to the world’s largest collection of Grandma Moses paintings. And in a nod to another American icon, Norman Rockwell’s 1943 painting “Freedom From Fear” features a copy of the Bennington Banner — the local newspaper still publishing today, 185 years after it began.
On Main Street, signs of challenge remain, including vacant storefronts. But many see momentum.
Few projects embody that optimism more than the long-shuttered Walloomsac Inn in Old Bennington. Older than the nation itself, the landmark once hosted multiple U.S. presidents. After two decades of decline, it’s now being restored by the firm Hendricks Churchill.
“A lot of people gave up on it,” said co-founder Rafe Churchill. “But this is a renovation — we’re fully resurrecting something.”
The goal: preserve as much historic detail as possible while reopening as a modern hotel.
“Our vision is rooted in bringing these historic buildings back,” said Casey Sunderland, “and using hospitality as a means to sustain them.”