72 Hours in the Okemo Valley
Vermont’s Okemo Valley is anchored by the Scenic Route 100 Byway, running through a network of postcard-worthy towns. Here, winding backroads reveal historic farmsteads, artist studios, century-old general stores, and some of the most inviting trails, tables, and cultural spaces in the state.
Ludlow, home to Okemo Mountain Resort, is a hub of four-season adventure. In Weston, classical theater meets country-store nostalgia. Grafton holds lovingly preserved buildings and bucolic meadows that reflect a community steeped in tradition. Chester’s charm runs deep, from stone-built architecture to welcoming cafes and craft galleries. Whether you’re hiking a ridgeline above Plymouth Notch, sipping cider in Mount Holly, or gallery-hopping in Londonderry, you’ll find that the Okemo Valley blends old Vermont character with fresh, creative energy.
Day one
SHREWSBURY, PLYMOUTH, READING
Begin your journey at Smith Maple Crest Farm in Shrewsbury, home to sugar makers who have tended the same rolling sugarbushes for generations. You can trace the syrup-making process from tree to table, sample maple syrups, and wander through history beneath trees that have witnessed two centuries of Vermont life.
From Shrewsbury, follow winding country roads to Plymouth Notch. Explore the President Calvin Coolidge State Historic Site, the perfectly preserved village where Coolidge was sworn in as the 30th president by lamplight in his boyhood home. Right next door, Plymouth Artisan Cheese, producer of one of America’s oldest cheddars, still crafts tangy, raw-milk cheddar, much as it did in Coolidge’s day.
Just down the road, you can fuel up at Chloe’s Market on the site of the old Plymouth Country Store with hearty breakfast sandwiches, homemade soups, and deli fare. The spirit of the market’s namesake, a beloved rescue dog, lives on through the owners’ donations to animal charities, a heartfelt slice of Vermont community spirit.
Art lovers can spend the afternoon in Reading at the Hall Art Foundation. Contemporary masterpieces by Warhol, Kruger, and Kiefer fill converted barns and a stone farmhouse beside a rushing waterfall. If winter’s in full swing, trade brushstrokes for snow tracks with Snowmobile Vermont, cruising forest trails that reveal the wild beauty of the Green Mountains.
Start winding down the day in Shrewsbury at Pierce’s Store, a historic general store turned cooperative hub, shelves brimming with local cheeses, maple syrup, and handcrafted goods by Shrewsbury artisans. It’s the perfect place to pick up a taste — or keepsake — of the town. For dinner, head to Rustic Rooster, a laid-back spot for fried chicken, pizza, and ribs under a covered patio.
Day Two
LUDLOW, MOUNT HOLLY, CHESTER
Start the day in Ludlow, a nexus of year-round mountain-town energy. First, grab a scratch-made breakfast at The Hatchery, where everything from the maple syrup to the sriracha is Vermont-made. Then, at Okemo Mountain Resort, ski southern Vermont’s tallest vertical drop in winter or take in the sunshine on a summer hike up to the 60-foot fire tower at the peak of Okemo Mountain, which provides panoramic views of the area. A few minutes away, Fox Run Golf Club presents an 18-hole championship course carved through rolling terrain, while winter brings seven miles of groomed Nordic trails and snowshoe routes along the Black River.
Maple lovers will appreciate the Green Mountain Sugar House in spring, its red roof reflected in Echo Lake as the sweet scent of boiling sap fills the air. Nearby, Crowley Cheese in Mount Holly continues a 200-year tradition of handmaking cheddar-style cheeses in its 1882 post-and-beam factory.
When it’s time to slow down, book a massage at Castle Hill Resort and Spa or browse Chester’s creative corners: DaVallia for handcrafted furnishings and design or Fischer Arts for nature-inspired books and gifts. Outdoorsy types can head to Camp Plymouth State Park for a lakeside picnic, a paddle, or a bit of old-fashioned gold panning in Buffalo Brook.
In October, grab a warm donut from New England Cider Donuts before browsing Mount Holly’s Cider Days festival of apples, crafts, and community. And if you’re passing through Chester before noon, make a stop at the Country Girl Diner, a gleaming 1940s Silk City Silver dining car where pancakes spill over the plate and pies are baked daily with Vermont butter.
For dinner, linger over wine-paired small plates at Stemwinder or enjoy pints and pub fare at The Killarney or The Loft Tavern. Alternatively, you can settle in by the fire at the stylish Main + Mountain Bar & Motel, a spot that makes it easy to go straight from cocktails around the firepit to your bed for the night. Other accommodation options include the historic Echo Lake Inn, featuring distinctly styled rooms and a restaurant that celebrates Vermont’s harvest, and Okemo Mountain Resort, a family-friendly base for every season.
Note that Chester and Ludlow are also both on the Inn to Inn Walking Tour route, a 40-mile loop that takes you to four of the region’s standout inns. The walk is self-guided but fully supported, including accommodation bookings, route maps and tips, luggage transport between inns, trails snacks, and dinner each night.
DAY THREE
GRAFTON, LONDONDERRY, WESTON
Begin your final Okemo Valley day in Grafton. One of Vermont’s best-preserved small towns, its white clapboard homes and weathered barns tell stories of centuries past. The historic Grafton Inn, open since 1801, anchors the village with antique-filled rooms, hand-hewn beams, and farm-fresh cuisine.
Step outside your door to find endless ways to explore. The Grafton Trails & Outdoor Center spans 2,000 acres of meadows and forest, offering year-round adventure — hiking, mountain biking, and disc golf in summer; cross-country skiing, tubing, and fat biking in winter. Stop by The Nature Museum to enjoy hand-painted dioramas, live honeybees, and the whimsical Magic Forest Playscape. For a cultural addition to your itinerary, spend the afternoon learning about resilience and freedom at the Turner Hill Interpretive Center, a site honoring Alec Turner, a formerly enslaved man who escaped from Virginia in 1862 and made his home here. Before you leave town, browse MKT: Grafton for picnic provisions and local favorites like Grafton Village Cheese, aged and crafted just down the road.
Further west in Londonderry, you’ll find a blend of alpine energy and artistic charm. Magic Mountain Ski Area is celebrated for its uncrowded slopes, naturally narrow and twisting decent, and laid-back vibe. The nearby Viking Nordic Center, meanwhile, is one of the oldest Nordic centers in the country. Maintaining a network of over 20 miles of trails, it’s known for being very family friendly, with rentals and lessons available for children and events like “cookie hunts” on the trails. South of town, Grandma Miller’s Pies & Pastries is a must-stop for sticky buns, cider doughnuts, and homemade pies baked in an iconic red barn. Nearby, pay a visit to Lasser Ceramics on the banks of the West River to see vibrant pottery being thrown and glazed.
There are plenty of lodging options in Londonderry as well. At Blue Gentian Lodge, gardens supply the kitchen, solar panels power the property, and the lodge’s Alpine namesake is a nod to its Swiss founders, who helped establish Magic Mountain. Another is The Upper Pass Lodge, a pet-friendly, slopeside stay at the base of Magic Mountain with a laid-back vibe, family suites, and a bar pouring exclusively Vermont-made spirits.
End your journey in Weston, where cultural heritage and craftsmanship converge. Weston Priory welcomes visitors to join the Benedictine monks in prayer and reflection amid gardens and orchards, while the Weston Theater Company, Vermont’s oldest professional theater, continues its legacy of world-class productions at Walker Farm. Don’t miss The Vermont Country Store, a living time capsule of penny candy, flannel nightgowns, and nostalgic goods that anchors Main Street much as it did in the mid-twentieth century.
As evening settles, raise a glass at Outer Limits Brewing, whose small-batch beers served in the mountain air mark a fitting toast to three days of exploration through some of southern Vermont’s most memorable villages.