72 Hours in The Shires of Vermont
Farm Charm and Homegrown Flavors
Cradled between the Green Mountains and the Taconics, The Shires region of Vermont preserves a rural way of life shaped by farming, community, and a strong connection to the land. Here in the state’s compact southwestern corner — where winding backroads lead to historic barns and vibrant villages — the landscapes closely follow the rhythm of the seasons. This is a place of deep roots, where small farms carry on well-worn traditions with a new generation’s spirit.
Spend a long weekend exploring the region’s farmstands and sugarhouses, pastures and producers — places where the doors are open and visitors are more than welcome. In Bennington, Revolutionary War history meets a fresh wave of creativity, while farther north in Manchester, Gilded Age estates share the hillsides with family-run orchards and organic farm markets. Along the way, stop in Shaftsbury, Dorset, and East Dorset, each offering its own take on The Shires’ blend of pastoral charm and modern-day makers.
Whether you’re enjoying baked goods with fresh eggs from a solar-powered farm, walking the rows of an heirloom apple orchard, or lingering over a locally grown meal, this is Vermont with its hands in the dirt and its heart wide open.
Day one
Sunderland and Shaftsbury
Settle into the quiet elegance of Hill Farm in Sunderland, a revitalized 70-acre farmstead once home to a dairy founded in 1779. Today, the property welcomes guests to a boutique inn, restaurant, and educational vegetable farm set in Vermont’s Equinox Mountain Valley. Wake up to mist rising off the Battenkill River and a complimentary just-harvested breakfast. Spend the day wandering garden beds, joining a culinary class, or fly-fishing on the nearby river.
From Sunderland, drive the scenic stretch of 7A into Shaftsbury to explore Wing & A Prayer Farm, where Merino sheep and alpacas mingle with peacocks and Shetland ponies. Visitors can schedule a private tour to browse the farmhouse shop or join a hands-on workshop, such as primitive sheep felting or natural dyeing, when those activities are on offer. End the daylight hours at the Robert Frost Stone House Museum, where the poet wrote “Stopping by Woods on a Snowy Evening.” Walk the orchard planted with descendants of Frost’s apple trees and follow a trail lined with plaques bearing his verse.
For dinner, head back to Hill Farm and grab a table at the on-site restaurant to enjoy wood-fired dishes from the farm’s harvest and nearby purveyors, all served with sweeping mountain views.
DAY TWO
Peru and Manchester
Begin the morning with another farm-fresh breakfast at Hill Farm — perhaps a warm frittata or house-made jam over sourdough — then head north into the Green Mountains. A short drive away, Peru’s New Spring Farm invites travelers to connect with the land through yoga in a converted barn sanctuary or meditative walks through meadows once used for lively barn dances.
Continue into Green Mountain National Forest, where 900 miles of trails crisscross eight wilderness areas, including Lye Brook and Peru Peak. Stop for lunch at J.J. Hapgood General Store in Peru, a beautifully restored village mainstay with a full lunch and dinner menu, a dedicated wood-fired pizza menu, a lively summer bar, and shelves stocked with local cheese, maple syrup, and pantry staples.
In Manchester, the connection to the land continues at North Meadow Farm, where guests can tour the dairy barn, sample cave-aged cheese, and pet rescue goats and rabbits in the interactive barnyard. Nearby, Dutton Farmstand sells produce grown within 50 miles, fresh cider, handmade fudge, and local gifts. Just down the road, Earth Sky Time Community Farm pulses with community spirit — bakers pull loaves from a wood-fired oven, artists share their work, and the farm store overflows with organic vegetables, sourdough breads, and fermented spreads.
Next, it’s time to explore Manchester’s cultural side. Browse local titles at Northshire Bookstore, a beloved indie shop and literary gathering space. Wander the sculpture-lined trails at the Southern Vermont Arts Center, or step inside its light-filled galleries showcasing regional artists past and present. Settle in for a meal at the center’s curATE Café, where artfully plated dishes mirror the creativity that surrounds you.
Cap the day at Hildene, once Robert Todd Lincoln’s summer estate, now a working farm and education center with seasonal cheesemaking workshops. The farm operates as a teaching model for sustainable agriculture, with regenerative practices, solar-powered barns, and a commitment to ethical land stewardship woven into every aspect of the property. Conservation is central to Hildene’s mission, from its on-site pollinator sanctuary to its efforts to protect native species and preserve working landscapes for future generations. As dusk settles, dine back in town at The Copper Grouse, where the menu proudly lists every Vermont farm it sources from — proof that here, every meal is rooted in place.
Vermont’s Farm to Table Food Scene
What makes Vermont’s food scene so special? It all starts at family-run spots like North Meadow Farm in Manchester. Join Mirna Valerio, a.k.a. “The Mirnavator,” as she makes some new friends and visits The Restaurant at Hill Farm in Sunderland for a meal that celebrates the heart of Vermont’s farm-to-table spirit.
DAY THREE
Dorset, Rupert, and Bennington
From Manchester, set your sights on Dorset, whose year-round farmers market buzzes each Sunday with fresh produce, live music, and armfuls of blooms from True Love Farm. If you’re visiting in the fall, pick apples at Mad Tom Orchard, where little red wagons, crisp mountain air, and still-warm cider donuts make for a perfect outing.
Continue on to the town of Rupert to explore Merck Forest & Farmland Center, Vermont’s first environmentally focused agricultural nonprofit. Join a Tree-to-Cutting-Board workshop, meet the farm’s animals, or hike through 3,100 acres of regenerative forest and pasture. At Merck, land stewardship isn’t just an ideal — it’s a way of life and a fitting way to deepen your connection to Vermont’s working landscape.
In the afternoon, journey south to Bennington, where flavor runs deep. Its Garlic Town USA event each late summer fills downtown with garlicky treats — pickles, cheese curds, even fudge — while Harvest Fest in October celebrates the season with food, games, and community spirit. Visit the Bennington Battle Monument for a taste of Revolutionary War history, then sip grain-to-glass bourbon or maple whiskey at Village Garage Distillery. For dinner, head to Pangaea in North Bennington, where seasonal menus showcase local farms, and the warm glow of a Vermont country store spills across the square from its sister business, Powers Market. Established in 1833, Powers has been the place to find unique Vermont mementos for nearly two centuries and is the perfect spot to pick up an end-of-trip souvenir.
Spend the afternoon at Lake St. Catherine State Park, a 117-acre natural area that wraps around a quiet lake. You can swim from the sandy beach, rent a pedal boat from the concession stand, or play a round of disc golf beneath the trees. As the sun dips low, keep an eye on the shoreline, as white-tailed deer often appear at dusk; every so often, moose pass through as well.
The Shires region of Vermont blurs the line between visitor and neighbor in the best possible way. Come for the mountain views and postcard-perfect villages and stay for the makers, the meals, and the quiet magic of a region rooted deeply in the land. The invitation is simple: slow down, dig in, and discover a Vermont that feels both timeless and entirely your own.