The Best of a Woodstock Fall Foliage Getaway | Happy Vermont

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woodstock fall foliage

The Best of a Woodstock Fall Foliage Getaway

Planning a Woodstock fall foliage getaway is a perfect choice for anyone looking to explore Vermont.

Consistently ranked as one of the best and most beautiful towns to visit, Woodstock is gorgeous and enjoyable any time of year. And when it comes to fall, this Windsor County town—home to covered bridges, cozy shops, and meandering dirt roads—offers loads of New England charm and autumn fun.

Patrick Fultz, who owns the Sleep Woodstock motel with his wife, Leslie Browne, says it’s possible to visit Woodstock several weekends in a row and not do the same thing twice.

“People ask us all the time, ‘Where should I go?’ We tell them to just slow down,” says Fultz, who is gearing up for a busy fall season. “It’s not about getting from point A to point B. There’s a whole bunch of stuff in between. Enjoy that because there’s so much beauty.”

Making the Most of a Woodstock Fall Foliage Getaway

woodstock fall foliage

-Sleepy Hollow Farm/Shutterstock

A Woodstock fall foliage visit can include everything from hiking and scenic drives to events, art, and culture. Here’s a round-up of places to visit in Woodstock and things to do in Vermont this fall.

Billings Farm & Museum in Woodstock

Billings Farm & Museum, a historic dairy farm, was founded in 1871. Billings Farm hosts a variety of fall events, including a Wagon Ride Weekend in September and a Harvest Celebration in October.  Visit for more information.

Stroll Along Woodstock’s Central and Elm Streets

In the heart of Woodstock are streets that are perfect for an autumn stroll. Central Street is home to the Yankee Bookshop, Vermont Eclectic Company apparel store, Unicorn gift shop, Mont Vert Cafe, and Soulfully Good Cafe. Elm Street is where you’ll find The Woodstock GalleryF. H. Gillingham & Sons general store, and Woodstock History Center, and more. Near the Village Green is The Woodstock Inn & Resort and Middle Covered Bridge.

woodstock fall foliage

-courtesy photo/Billings Farm

Marsh-Billings-Rockefeller National Historical Park

Vermont’s only national park is where visitors can tour a mansion and gardens, hike trails around Mount Tom, and visit the conservation stewardship exhibit at the Carriage Barn Visitor Center. Visit for more information.

Fall Views on Mount Peg Overlooking Woodstock

An easy hike up Mount Peg offers panoramic views of Woodstock and the surrounding hills.  Enjoy a picnic when you reach the 1,080-foot summit and soak up the fall beauty.  Visit for more information.

Vermont Institute of Natural Science (VINS)

Visit VINS, an environmental education and avian rehabilitation organization in nearby Quechee, to see raptors, songbirds, reptiles, and more. Walk nature trails and explore the exceptional Forest Canopy Walk. Visit for more information.

Simon Pearce

Along the banks of the Ottauquechee River and next to the Quechee Covered Bridge is Simon Pearce’s Flagship Store and Restaurant. The location’s glassblowing studio offers the opportunity to watch artisans create functional and beautiful works of art. Visit for more information.

Scenic Fall Foliage Drives

Woodstock offers plenty of scenic roads to explore. From the center of town, take Route 106/South Road through South Woodstock, where you’ll find the South Woodstock Country Store and the Kendron Valley Inn’s Ransom Tavern.

Also try Route 12 from Woodstock to Barnard for scenic rolling hills, a country store, and a rural landscape, or follow Route 12 to Pomfret Road to Suicide Six ski area.

For more information about Woodstock, visit

woodstock fall foliage

-Photo courtesy of Sleep Woodstock

Happy Vermont Podcast

Patrick Fultz and Leslie Browne wanted to buy a house in Woodstock. Instead, they end up purchasing and renovating the 12-room Sleep Woodstock motel on Route 4 in 2013.  In this episode, “Slowing Down and Finding Happiness in Woodstock,” the couple talk about why they decided to move to Vermont and what advice they give to guests who are visiting the area.

Listen to the podcast on Podbean.


Fall & Autumn, Getaways, Scenic Drives, Things To Do, Travel Tips, Vermont Podcast, Windsor County, Woodstock
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