The Best of Vermont: An Eight Day Travel Itinerary

Hills covered in fall foliage across a lake in Wilmington, Vermont.

Fall foliage in Wilmington, Vermont. Photo © Kimberly Vardeman, licensed Creative Commons Attribution.

The best way to explore Vermont is to get in a car and hit the back roads, stopping at country stores and maple sugar farms nestled in Green Mountain valleys. This itinerary takes in a mix of Vermont’s prime attractions in an easygoing circle around the state.

Day 1

Start in Brattleboro. Spend the day exploring Brattleboro’s artsy attractions, including the Brattleboro Museum & Art Center and the Estey Organ Museum, and leave enough time for shopping on quirky Main Street. Time your visit to correspond to the first Friday night of the month to experience Brattleboro’s Gallery Walk and soak in the creative spirit of the city.

Day 2

From Brattleboro head north along winding Route 30, stopping for a stroll around Newfane’s village green before taking the turn north onto Route 35 to Grafton (45 min.). Here, take a tour of the Grafton Village Cheese Company and the town’s small Nature Museum before a meal and stay at the historic Grafton Inn.

Day 3

Head west on Routes 121 and 11, then north on Route 100 to Weston (30 min.), where you’ll need at least an hour to really explore the phenomenon that is the Vermont Country Store. After lunch, continue north along scenic Route 100 to Plymouth (35 min.) to stand in the company of greatness at the President Calvin Coolidge State Historic Site. Push on north along 100A and east on Route 4 to spend the night at the Woodstock Inn & Resort in Woodstock (25 min.).

Day 4

Spend the morning with Vermont’s star bovines at Woodstock’s Billings Farm & Museum. (For a true treat, time your visit with the farm’s Cow Appreciation Day.) Then take in the scenic drive north along Route 12, east on Route 107, and then north along Route 100, ending up in the Mad River Valley town of Warren (90 min.). Spend the afternoon exploring The Warren Store and the picturesque village center or take advantage of the many recreational opportunities with a hike up Camel’s Hump or Mount Ellen, a bike ride through town, or a wild canoe ride on the Mad or Winooski River.

Day 5

Head north along Route 100 to Waterbury (30 min.) for a morning tour of the Ben & Jerry’s Factory. (It’s never too early for Chunky Monkey!) Then it’s off to the big city! Drive west along I-89 to the big ol’ college town of Burlington (45 min.). Spend the morning strolling among the shops on Church Street before heading to the waterfront in the afternoon for a visit to the ECHO Lake Aquarium and Science Center or Lake Champlain Maritime Museum. Tonight, take in a show at the Flynn Center for the Performing Arts.

Day 6

Push on south down Route 7 to Middlebury (1 hr.), where you can get a morning tour of Middlebury College’s pristine gray granite campus. After lunch, head east along Route 125 to commune with Vermont’s favorite adopted son via a hike along the meditative Robert Frost Interpretive Trail.

Continue south down Route 7 to the covered bridge capital of Proctor (35 min.), visiting the paean to all things European, Wilson Castle. Stop for lunch in nearby Rutland (15 min.) and then drive to sophisticated Manchester (50 min.) for an afternoon of outlet shopping.

Day 7

Spend the morning driving up the Mount Equinox Skyline Drive for a beautiful view of the Green Mountains. Then head south down Route 7 to Bennington (40 min.), where you can check out the Bennington Battle Monument and the distinctive folk art of Grandma Moses at the Bennington Museum before spending the night in Bennington.

Day 8

Spend your last day tracing the meandering Route 9 east over the Green Mountains to the Back to the Future downtown of Wilmington and the quirky college town of Marlboro. If you haven’t yet gotten your farm fix, take a detour up Route 100 to visit Adams Family Farm for a sleigh ride or hayride before spending one last night in Brattleboro.


Excerpted from the Third Edition of Moon Vermont.

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