During our decade in New York City, I often sought escapes that offered both tranquility and charm. One crisp fall weekend, my friend Fran and I found ourselves in Chester, Vermont...a town that felt like stepping into a storybook. With its historic stone buildings, vibrant foliage, and welcoming locals, Chester provided the perfect backdrop for reconnecting with nature and each other.
More Things to Do in Chester, VT
Feeling the chill at Buttermilk Falls
Buttermilk Falls looked like something out of a storybook—tucked between maples, cascading down in elegant silver ribbons. The water was cold, clear, and fast, and the air smelled like wet leaves and stone. Fran and I climbed down carefully, finding the perfect rock to sit and listen. I remember thinking, “This is where time goes when it slips away.”
What I Loved Most: Watching leaves spiral into the pool, spinning in slow circles before continuing downstream.
Plan your day trip:
- Drive Time from Chester: ~20 min via VT-103 N
- Vibe: Serene, natural, hidden
- Highlights: Waterfall, swimming hole (warmer months), fall foliage
- Best Time to Visit: Spring for flow, fall for color
- Cost: Free
- Hours: Always open
- Address: 993 Buttermilk Falls Rd, Ludlow, VT 05149
Walking through time in the Stone Village Historic District
The Stone Village felt like a place frozen in the softest light. Rows of 19th-century homes built from local granite stood quietly behind picket fences and red sugar maples. Fran and I walked slowly, admiring the craftsmanship, the symmetry, the weight of time made beautiful. I remember thinking, “These homes have seen more seasons than I can imagine—and they’re still standing proud.”
What I Loved Most: The way each house had its own garden or quirky mailbox, like the past was still having quiet conversations with the present.
My highlights? Taking turns guessing what each house had been—a schoolhouse? A carriage stop? A dream home still being lived in.
Plan your day trip:
- Location: North St & Church St intersection, Chester
- Vibe: Historical, stately, timeless
- Highlights: 19th-century stone houses, fall foliage, photography
- Best Time to Visit: Autumn for peak charm
- Cost: Free walking tour
- Hours: Always open
- Address: Stone Village, Chester, VT 05143
Stepping inside quiet wonder at Whiting Library
We hadn’t planned to stop at the library, but when the wind picked up, we ducked inside—and it turned out to be one of our favorite moments. Whiting Library was warm, calm, and full of stories, both written and lived. Fran found a chair in the sun-drenched window, flipping through an old Vermont photo book while I browsed local history displays. I remember thinking, “Libraries are still the safest kind of magic.”
What I Loved Most: The creaky wood floors and handwritten notes from local children displayed on a bulletin board near the front desk.
My highlights? Finding a staff-recommended mystery novel that ended up being our road trip audiobook for the rest of the weekend.
Plan your day trip:
- Drive Time from Village Green: 2-minute walk
- Vibe: Cozy, thoughtful, community-driven
- Highlights: Vermont history books, quiet reading spaces, local art displays
- Best Time to Visit: Afternoon for soft light and warm reading nooks
- Cost: Free
- Hours: Tue–Sat, 10 am–6 pm
- Address: 117 Main St, Chester, VT 05143
Soaking up small-town magic on Chester Village Green
The heart of Chester pulsed from the Village Green. It was all there—white-steepled churches, historic inns, little shops, and fiery sugar maples circling the park like watchful sentries. Fran and I wandered the sidewalks with no plan, ducking into bookstores, admiring window displays, and sipping cider like it was our job. I remember thinking, “This is Vermont distilled into a square block.”
What I Loved Most: Sitting on a bench with fallen leaves at our feet, watching kids chase each other through piles while church bells rang in the distance.
My highlights? Picking up locally made candles from a weekend craft tent and sharing a cinnamon bun from a corner bakery while it was still warm.
Plan your day trip:
- Location: Main Street, Chester Village
- Vibe: Classic New England, festive, walkable
- Highlights: Shopping, leaf-peeping, seasonal festivals
- Best Time to Visit: September–October for peak foliage and fall markets
- Cost: Free to explore
- Hours: Shops generally open 10 am–5 pm
- Address: Chester Village Green, Chester, VT 05143
Unearthing surprises at the Lost Mine
Fran and I found the Lost Mine almost by accident—just a small sign off a wooded road, rustling leaves, and that Vermont kind of silence. We followed the trail past mossy rocks until the earth opened up into a small, unexpected shaft, remnants of a time when dreams were dug from the ground. I remember thinking, “This is the kind of history that hides until you're quiet enough to hear it.”
What I Loved Most: Reading the weathered mining plaques while golden leaves spun down around us like confetti from another century.
My highlights? A thermos of mulled cider we’d packed from the car, still warm, shared beside the old stone walls under the fiery canopy of October maples.
Plan your day trip:
- Location: Just outside Chester center—ask locals for directions
- Vibe: Quiet, mysterious, tucked-away
- Highlights: Trail, abandoned mine shaft, historic markers
- Best Time to Visit: Fall for foliage and crisp air
- Cost: Free
- Hours: Dawn to dusk
- Address: Near Smokeshire Rd, Chester, VT 05143
Spinning creativity at Endless Creations Pottery Studio
Endless Creations felt like walking into someone’s beautiful mess—in the best possible way. Shelves of hand-thrown mugs, glaze-splattered aprons, and the quiet hum of inspiration everywhere. Fran and I each picked a mug, touched with the thumbprint of the artist, and then stayed longer than we expected just watching the wheel in motion. I remember thinking, “This is what handmade feels like—you can see the person in the piece.”
What I Loved Most: Seeing the work-in-progress shelf—dozens of soft, clay-gray forms waiting to become something beautiful.
My highlights? Bringing home matching mugs with pine tree glazes. Mine’s still on my desk, full of pens and Vermont memories.
Plan your day trip:
- Location: Just off Route 103 in Chester
- Vibe: Artistic, welcoming, tactile
- Highlights: Handmade pottery, wheel demos, local artist work
- Best Time to Visit: Weekdays for quieter browsing
- Cost: Mugs and bowls ~$20–$40
- Hours: Mon–Sat 10 am–5 pm
- Address: 23 Maple St, Chester, VT 05143
Discovering craftsmanship at Smokeshire Design
Smokeshire Design was part gallery, part workshop, part soulful surprise. Fran and I wandered through its warm, wood-filled space admiring everything from reclaimed barn wood tables to sculptural lighting fixtures that looked like art installations. I remember thinking, “This is design that feels lived in.” Every corner told a story—of materials, of makers, of Vermont itself.
What I Loved Most: Running my hand along a smooth cherry table with butterfly joints, knowing it was made just a few feet from where we stood.
My highlights? Fran bought a hand-turned wooden bowl for her kitchen; I brought home a candle holder made from local slate. Both came wrapped with care and a story.
Plan your day trip:
- Drive Time from Village Green: ~5 minutes
- Vibe: Refined, rustic, deeply intentional
- Highlights: Custom furniture, Vermont materials, artisan craftsmanship
- Best Time to Visit: Fall, when wood grains glow in afternoon light
- Cost: Small pieces ~$30+, large custom furniture available
- Hours: Most days 10 am–5 pm; call ahead for custom tours
- Address: 363 VT-103 S, Chester, VT 05143
Savoring nostalgia at Country Girl Diner
Country Girl Diner was exactly the kind of place you hope to find in Vermont—an original 1950s railcar diner, still humming with conversation and coffee. We slid into a red vinyl booth, steam rising from mugs, and the waitress called us “hon” without thinking. I remember thinking, “This is breakfast that remembers who you are.”
What I Loved Most: The handwritten specials on the chalkboard: apple cinnamon pancakes, real maple syrup, local sausage. Every bite was love on a plate.
My highlights? I ordered the corned beef hash with poached eggs and rye toast. Fran had the pumpkin pancakes with maple butter. We cleaned our plates and didn’t speak until we were halfway through coffee refills.
Plan your day trip:
- Location: South Main Street, just outside town center
- Vibe: Vintage, cozy, locals-loved
- Highlights: All-day breakfast, Vermont maple syrup, diner charm
- Best Time to Visit: Morning for full menu and warm crowd
- Cost: Most meals under $15
- Hours: Wed–Sun, 7 am–2 pm
- Address: 46 VT-103, Chester, VT 05143
Resting well at the Fullerton Inn and Restaurant
The Fullerton Inn welcomed us with creaky floors, warm lamps, and a porch draped in fall leaves. Fran and I checked in just before sunset and dropped our bags by the window to watch the amber light stretch across the village. I remember thinking, “This is the kind of place that lets you rest differently.”
What I Loved Most: Sitting in the downstairs tavern after dinner with glasses of wine and nowhere else to be.
My highlights? Dinner in the inn’s restaurant: butternut squash soup, roasted chicken with root vegetables, and apple crisp with homemade vanilla ice cream. Comfort layered on comfort.
Plan your day trip:
- Location: Directly on Chester Village Green
- Vibe: Historic, welcoming, romantic
- Highlights: Colonial charm, restaurant, porch views
- Best Time to Visit: Fall for color and cozy fireside nights
- Cost: Rooms from ~$120/night; dinner entrees $20–$30
- Hours: Check-in 3 pm; tavern open evenings
- Address: 40 The Common, Chester, VT 05143
Artful treasures at DaVallia Gallery and Boutique
We spent our final afternoon in Chester dipping in and out of its most beautiful shops—DaVallia Gallery and Sage among them. The gallery felt like a quiet forest of creativity—ceramics, fiber arts, original sculpture—while Sage sparkled with handmade jewelry and gifts that felt meaningful, not mass-produced. I remember thinking, “If I lived here, this would be my go-to for every birthday, holiday, and rainy day.”
What I Loved Most: A silver leaf pendant I almost didn’t buy—Fran insisted, and now I wear it when I need a little Vermont in my day.
Plan your day trip:
- Location: Short walk from the Village Green
- Vibe: Thoughtful, curated, inspiring
- Highlights: Local art, handmade jewelry, unique gifts
- Best Time to Visit: Fall for seasonal collections and cozy ambiance
- Cost: Small gifts from ~$20; art pieces vary
- Hours: 11 am–5 pm most days
- Address: 78 The Common and 61 The Common, Chester, VT 05143
Finding beauty in the details at Sage Jewelry and Gifts
Sage felt like walking into a jewelry box filled with light. The shop was small but curated with heart—glass cases of handcrafted rings, nature-inspired earrings, tiny sculptures, and gifts that felt like they already knew who they were for. Fran and I explored every shelf slowly, pausing to hold pieces that seemed to whisper, “Take me home.” I remember thinking, “This is what happens when someone puts their soul into a store.”
What I Loved Most: The mix of Vermont-made pieces and hand-selected treasures from small makers—it all felt personal and full of care.
My highlights? A set of sterling silver earrings shaped like mountain ridgelines and a hand-stitched journal with a pressed-leaf cover. Fran found a delicate scarf with hand-painted fall foliage that looked like it belonged in the Chester woods.
Plan your day trip:
- Location: Just off the Village Green
- Vibe: Elegant, heartfelt, thoughtfully curated
- Highlights: Jewelry, scarves, artisan gifts, seasonal items
- Best Time to Visit: Fall for warm-toned pieces and gift inspiration
- Cost: Jewelry from ~$25; gift items vary
- Hours: Typically 11 am–5 pm, closed some weekdays
- Address: 61 The Common, Chester, VT 05143
Conclusion: Embracing the Heart of Chester
Our journey through Chester was more than just a series of stops; it was an immersion into a community rich with history, artistry, and warmth. From the serene trails of the Lost Mine to the handcrafted treasures at local boutiques, every moment was a reminder of the beauty found in simplicity. As we departed, the golden hues of autumn leaves mirrored the lasting impressions Chester left on our hearts.
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