During our decade in New York City, Chris and I often sought solace in the quiet corners of New England. Bennington, Vermont, became one of those cherished retreats...a place where history whispers through covered bridges and art blooms in unexpected galleries. In the gentle embrace of spring, we found ourselves meandering through its storied streets, discovering the charm that makes Bennington a perfect day trip or weekend getaway.
Best Things to Do in Bennington, VT
Gazing over history at Bennington Battle Monument
The elevator doors opened and suddenly the whole valley stretched beneath us—rolling green, budding trees, the distant shimmer of the Walloomsac. Spring sunlight spilled through the narrow windows, and I remember thinking, “The past feels lighter from up here.”
What I Loved Most: Watching storm-colored clouds drift over the Green Mountains while the monument stayed perfectly still.
My highlights? Celebratory pints and a maple-bourbon burger at Kevin’s Sports Pub & Restaurant—comfort food that tasted like victory after climbing all those stone steps to the entrance.
Plan your day trip:
- Drive Time from downtown Bennington: 5 min / 1.5 mi
- Vibe: Patriotic, panoramic, grounding
- Highlights: Observation deck, Revolutionary War exhibits, gift shop
- Best Time to Visit: April–October when the tower is open
- Cost: ~$6 adults
- Hours: 9 am–5 pm, seasonal
- Address: 15 Monument Cir, Bennington, VT 05201
Tracing folk art memories in Bennington Museum
An old school bell rang faintly as we stepped into the Grandma Moses Gallery—paintings of winters long gone, summers endless and green. I felt a tug of nostalgia for scenes I’d never lived. Chris whispered, “It feels like looking into someone else’s childhood,” and I nodded, swept up in brushstrokes of sugaring-off parties and one-room schools.
What I Loved Most: The 1865 Johnson schoolhouse, sun-washed and smelling faintly of pine, preserved inside the museum.
My highlights? A slice of peach pie and dark roast at the museum café—simple, sweet, perfectly Vermont.
Plan your day trip:
- Drive Time from downtown Bennington: 2 min / 0.5 mi (easy walk)
- Vibe: Reflective, artistic, quietly inspiring
- Highlights: Grandma Moses collection, early Vermont artifacts, rotating exhibits
- Best Time to Visit: Year-round; rainy days feel extra cozy
- Cost: ~$12 adults
- Hours: Thu–Mon 10 am–4 pm
- Address: 75 Main St, Bennington, VT 05201
Listening to river whispers at Silk Covered Bridge
The newly leafed maples framed the bridge in soft green, and the Walloomsac murmured beneath its timber trusses. We strolled slowly, our footsteps echoing against worn planks. I thought, “This bridge held stories long before we arrived—and will long after we’re gone.”
What I Loved Most: Leaning on the side opening, watching petals float downstream like tiny boats.
My highlights? Post-bridge treats: pistachio gelato from a downtown scoop shop—cold and bright against the warm wood smell still on our hands.
Plan your day trip:
- Drive Time from downtown Bennington: 7 min / 2.5 mi
- Vibe: Rustic, nostalgic, photogenic
- Highlights: 1840s lattice truss, river views, picnic spot
- Best Time to Visit: Spring for blossoms; fall for foliage reflections
- Cost: Free
- Hours: Always open to pedestrians
- Address: Silk Rd, Bennington, VT 05201
Pausing in history at Historic Burt Henry Covered Bridge
A mile downstream, the Burt Henry Bridge wore its age proudly—faded red boards, hand-hewn beams. Chris ran a palm along the grain and said, “Imagine who crossed here in horse-drawn carts.” The river answered with a low rush, and for a moment the present slipped away.
What I Loved Most: Watching late-afternoon sun stripe the interior, lighting dust motes like tiny lanterns.
My highlights? A shared maple creemee (soft-serve) from a roadside stand—sugary, sticky, worth every drip.
Plan your day trip:
- Drive Time from downtown Bennington: 8 min / 3 mi
- Vibe: Quiet, storied, time-capsule
- Highlights: 1835 covered bridge craftsmanship, river access, photography
- Best Time to Visit: Golden hour for perfect light
- Cost: Free
- Hours: Always open
- Address: 180 River Rd, North Bennington, VT 05257
Romantic Activities and Attractions:
Finding drama at Oldcastle Theatre Company
The black-box stage felt intimate—no velvet curtains, just raw storytelling. We caught an evening play about small-town secrets; every line landed like a whispered confession. I thought, “This is why live theatre matters—it lets strangers feel something together.” Walking out into cool night air, the streetlights seemed softer somehow.
What I Loved Most: The talk-back session after the show, where actors chatted like neighbors.
My highlights? Pre-show dinner at The Publyk House: maple-glazed salmon, warm cheddar biscuits, and candlelight that lingered in my mind through the final act.
Plan your day trip:
- Drive Time from downtown Bennington: 3 min / 0.7 mi
- Vibe: Intimate, creative, thought-provoking
- Highlights: Professional productions, post-show discussions
- Best Time to Visit: Evenings; check season schedule
- Cost: ~$25–$39 tickets
- Hours: Box office opens 2 hr before curtain
- Address: 331 Main St, Bennington, VT 05201
Wandering grand halls at Park-McCullough Historic House
Morning drizzle left the gardens glistening; tulips nodded along brick pathways while the Victorian mansion stood dignified and dreamy. Inside, every room felt frozen in a gilded sigh—velvet settees, ornate mirrors, sun slanting through lace curtains. I whispered, “Imagine hosting summer soirées here,” and Chris answered with a ballroom twirl that made me laugh out loud.
What I Loved Most: The porch swing facing the carriage barn—perfect for listening to robins and far-off church bells.
My highlights? Post-tour picnic: Benner’s Pizza slices (white pie with garlic and spinach) on the mansion lawn—historic elegance meets cheesy comfort.
Plan your day trip:
- Drive Time from downtown Bennington: 6 min / 2 mi
- Vibe: Victorian, romantic, storybook
- Highlights: Guided tours, carriage barn, seasonal gardens
- Best Time to Visit: May–October for full house and garden access
- Cost: ~$15 guided tour
- Hours: Fri–Mon 10 am–4 pm, seasonal
- Address: 1 Park St, North Bennington, VT 05257
Soaking in campus creativity at Bennington College
We ended our Bennington circuit with a stroll through the college greens. Cherry blossoms flurried across modernist buildings; student sculptures dotted the lawn like quiet questions. I thought, “Learning feels alive here—unruly in the best way.” Chris found an outdoor piano and plunked out a tune that drifted into the budding maples.
What I Loved Most: The view from Jennings Music Building—rolling hills framed by tall windows, sunlight dancing on hardwood floors.
My highlights? A café latte at the campus Commons, shared with a student eager to chat about art theory—an impromptu lesson in thinking differently.
Plan your day trip:
- Drive Time from downtown Bennington: 10 min / 3.5 mi
- Vibe: Intellectual, free-spirited, leafy
- Highlights: Jennings music hall, sculpture walk, seasonal performances
- Best Time to Visit: Spring or fall when campus tours run
- Cost: Free self-guided walking; ticketed events vary
- Hours: Grounds open daily; check calendar for events
- Address: 1 College Dr, Bennington, VT 05201
Conclusion: Embracing the Timeless Charm of Bennington
Bennington offered us more than just a break from the city's hustle; it provided a tapestry of experiences woven with history, art, and natural beauty. From the towering Bennington Battle Monument to the serene paths of Bennington College, each moment felt like a step back into a simpler, more connected time. As we departed, the echoes of our laughter on covered bridges and the warmth of shared meals lingered, reminding us that sometimes, the most profound journeys are the ones that bring us closer to ourselves and each other.
Explore More Vermont Adventures
Jump to a Spot...
- • Gazing over history at Bennington Battle Monument
- • Tracing folk art memories in Bennington Museum
- • Listening to river whispers at Silk Covered Bridge
- • Pausing in history at Historic Burt Henry Covered Bridge
- • Finding drama at Oldcastle Theatre Company
- • Wandering grand halls at Park-McCullough Historic House
- • Visit the Scenic Paper Mill Village Bridge Over the Walloomsac River
- • Soaking in campus creativity at Bennington College