Fall 2018 New England Road Trip Guide: The Definitive Vermont Foliage Tour

Three days, 497 miles, and a whole lot of trees.

fall road trips vermont foliage tour

Painterly autumn leaves in Killington, Vermont. / Carl D. Walsh/ Aurora Photos

Total Round-Trip Mileage: 497

Day One
Gas up the Subaru and order a large latte at Dunks: You’ll be grateful for the caffeine during the three-hour journey to Wilmington, your first stop along Vermont’s Scenic Route 100 Byway. Soak up vibrant beeches and sugar maples—and grab lunch at Dot’s, an old-school favorite for spicy chili and blue-plate turkey specials—before detouring to Hogback Mountain, where you can stretch your legs on wooded trails. When you’re sufficiently tuckered out, head back to the car and drive through foliage-friendly Dover and Wardsboro to reach the Windham Hill Inn, in West Townshend. Boasting guest rooms with Green Mountain views, it’s the ideal place to recharge before tomorrow’s adventure.

Miles Traveled: 164

Day Two
Rise and shine! Today’s first order of business? Brunch at the Bryant House, in Weston. Tuck into molasses-laced johnnycakes or gooey grilled cheese (made with Green Mountain State fromage, of course) in the 19th-century dining room, then walk next door to browse locally made goodies (small-batch preserves, maple-leaf candy) at the Vermont Country Store. You’ll want something sweet to nibble on for the colorful ride through Ludlow and Plymouth, the perfect spot to pick up Route 100A for a jaunt to Long Trail Brewing Company’s riverside pub, in Bridgewater Corners. Your final stop—after a potential moose sighting on the road through Granville—is the luxe Pitcher Inn, in Warren, where Garnier-Thiebaut linens, soaking tubs, and a farm-to-table restaurant with a 500-deep wine cellar await.

Miles Traveled: 96

Day Three
Make the most of your last day with an in-room massage before grabbing a quick bite at Three Mountain Café—the birthplace of Green Mountain Coffee Roasters—in Waitsfield. Ready to head south? Count all the covered bridges you see as you make the tree-lined trek to Snowshed Adventure Center at Killington Resort. Here, you can test your agility on the outdoor obstacle course, traverse the mountain with a guided ATV tour, or soar through the air on a zipline—by far the most adventurous way to take in those autumn leaves. Cap off your voyage with a hard-earned meal at Honeypie, in Jamaica, near the junction of Routes 100 and 30. Run by the owners of the James Beard–nominated SoLo Farm & Table, the restaurant serves up classic burgers, hand-cut fries, and shakes made with organic, locally sourced dairy—hearty fuel for the long, winding, and unbelievably beautiful road home.

Miles Traveled: 237

More: Five Fabulous Ways to See New England This Fall