With a couple of days to explore Southern Vermont, stick to the eastern side of the Green Mountains and discover art, farms, and historic villages, with plenty of time to take the long way home.
Enjoy a leisurely, maple syrup-drenched breakfast at one of Woodstock’s gracious B&Bs, then head to Billings Farm & Museum to meet a beauty queen herd of Jersey cows, ride a hay wagon, and learn to churn your own butter. History buffs can continue next door to the well-preserved mansion at Marsh-Billings-Rockefeller National Historical Park, but if you’re primed for more agricultural excitement, opt for a quick trip to Sugarbush Farm to learn about the sugarmaking process while sampling farm-made cheese and syrup.
Pick up some picnic supplies at the Woodstock Farmers’ Market store as you head back through town to President Calvin Coolidge State Historic Site, where outdoor tables have an idyllic view of “Silent Cal’s” childhood home. Trace his path from the rural family homestead to the White House, then graze award-winning cheddar at nearby Plymouth Artisan Cheese.
Turn back up Route 100A toward Bridgewater Corners, where you’ll toast Vermont’s thriving beer scene at Long Trail Brewing Company, then spend the rest of the afternoon strolling Woodstock’s art galleries and shops, or cooling off in an Ottauquechee River swimming hole. If you’re feeling romantic, cozy up over regional Italian fare at itsy-bitsy Osteria Pane e Salute; if not, join a friendly crowd of locals for craft beer and burgers at Worthy Kitchen, Woodstock’s unofficial living room.
Wake up early for a sunrise hike up Mount Tom, then hit the road to explore some of Vermont’s most scenic byways. If you’ve already visited Plymouth Notch, the best way to Grafton is south on Route 106 to Route 10 and Route 35 South. Stroll through the perfectly preserved village center, and eat enough of the excellent aged cheddar at Grafton Village Cheese Company to keep you going to Brattleboro, where Superfresh! Organic Café is the perfect place to meet the locals over vegan grain bowls, “mylk,” and hearty salads.
Use the café Wi-Fi to download a map of Brattleboro’s latest art gallery exhibits, then visit the remarkable collections of fine arts, crafts, and photography in the walkable downtown. If it’s apple picking season (mid-August through October), trace the Connecticut River Valley north to Dummerston, where Scott Farm Orchard is a sublime place to fill your suitcase with a funky variety of apples, quince, and medlar.
Take I-91 all the way to Route 4 west so you can visit the tiny town of Quechee. Hike into Vermont’s deepest gorge at Quechee State Park, then head to Simon Pearce to watch a team of expert glassblowers shape the elegant wineglasses for sale upstairs in the gallery showroom. Stay in Quechee for dinner—Simon Pearce has a beautiful on-site restaurant—or head back to Woodstock for a meal at Richardson’s Tavern, an informal pub inside the elegant Woodstock Inn.