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Wanderlust in Woodstock, VT

I called Woodstock, VT home for two years. It was a dream.

I had originally set out to relocate with quintessential New England in mind. Boy, did I find it. One could easily describe Woodstock as a real-life Stars Hollow (for all you Gilmore Girls connoisseurs). The town is cozy, vibrant, and outright bucolic. In fact, I had never heard the word “bucolic” used until I moved to Vermont.

In all seasons, I highly recommend taking a drive to enjoy some time in this quaint New England town in Central Vermont.

Where to Eat & Drink: A Few Favorites

Cloudland Farm  – My top recommendation in all of Woodstock. Cloudland’s restaurant opens for weekend dinners, priding itself on farm-to-fork fare. The majority of produce and meat on your plate have been grown and raised directly on Cloudland Farm, while all other ingredients (such as bay leaves) are locally sourced. Their wraparound porch and hilltop view make for a magical evening.

Simon Pearce – A special occasion spot outfitted with Simon Pearce handblown glass and ceramics. Whether you want a prolonged meal or casual snack, both the restaurant and (newly renovated) bar have what you’re looking for. Be sure to peruse their in-house shop, downstairs glassblowing studio, and neighboring waterfall from the deck.

Woodstock Farmers’ Market  – A haven for the finest Vermont-made products. In addition to top-notch cheeses and wine, WFM also boasts incredibly delicious salads and sandwiches. Grab your food of choice and enjoy some time on their outdoor picnic tables along the Ottauquechee River.

Worthy Kitchen  – Beer lovers, unite! Worthy Kitchen has a long list of cool and interesting beers in celebration of Vermont’s vibrant brewing culture. What’s more, you can pair your beer (or wine or soda) with their deliciously casual menu chock-full of local favorites.

Wild Roots  – A short drive will land you at this new, buzz-worthy restaurant in Royalton, VT. Known for food of quality sustenance, Wild Roots sources from all local farms to provide an ever-changing menu with the seasons.

Things to Do: Explore Woodstock

Woodstock Town Hall Theater  – The quaintest theater you may have ever seen. Held in the Woodstock Town Hall, the showings can also be accompanied by your very own bucket of maple butter popcorn from concessions.

Woodstock History Center  – Woodstock is rich in agricultural and New England heritage. However, my favorite part of this History Center is their backyard. Grab a sandwich from the neighboring butcher shop or pack your own picnic and spend the afternoon on their lush lawn next to the river. The best part? This yard has one of the best views of Woodstock’s Middle Covered Bridge.

F.H. Gillingham & Sons  – A wonderful country store with historical significance. Established in 1886, F.H. Gillingham & Sons resides in its original building in the heart of Woodstock. This store offers everything, from Vermont cheese and maple syrup, to flannel shirts and local beer.

Billings Farm & Museum  – No trip to Woodstock is complete without a visit to Billings Farm. Get your adorable Jersey cow fix and learn a bit about Woodstock’s renowned agricultural history.

Marsh-Billings-Rockefeller National Historical Park  – Across the street from Billings Farm sits Mount Tom. Clear your mind while spending time in nature. You can amble along the wide, sloping carriage trail toward the summit that overlooks the entire Woodstock Village. Don’t forget to make a pitstop on the trail at the glorious Pogue pond before heading to the top!

Farmhouse Pottery  – An artisanal pottery studio that has gotten a substantial amount of attention lately. See what all the buzz is about and visit their beautiful store and studio. You can even book a Clay Date (https://www.farmhousepottery.com/products/wheel-workshop) with one of their potters for you and yours.

Quechee Gorge  – Known as Vermont’s Little Grand Canyon, it’s worth looking over the bridge and into the gorge at every season. You can also enjoy a meandering walk along the trail below the bridge!

Whisper Hill  – The zen duo behind Whisper Hill’s handcrafted bath and body products and produce deliciously scented candles. Their all-natural focus has resulted in extremely gentle and nourishing products without chemicals and synthetics. Find them by the Quechee Gorge, next to the large Antique Mall.

Silver Lake  – Take some tranquil time for yourself and picnic alongside beautiful Silver Lake. The Barnard Country Store across the street can provide all the snacks you need. There is simply something about lakeside lounging that I consider so quintessential Vermont.

Plymouth Cheese – Vermont is known for its cheese, and we are lucky enough to have an award-winning factory next door in Plymouth, VT. Situated in the historic and beautiful Calvin Coolidge Homestead , the factory is over 125 years old and is known as the second oldest cheese factory in the U.S. Jesse Werner and Sarit Melmed have revived the the building to create their very own line of colorfully waxed cheeses, all made and sold here.

Shackleton Thomas  – Located on the far side of the Bridgewater Mill, Shackleton Thomas boasts a showroom full of warm wooden hues and blue glazed pottery. Their hand-carved furniture and beautifully patterned ceramics are worth a gander for all who prize artisanal craftsmanship.

Andrew Pearce  – Operated by the son of Simon Pearce, Andrew and his wife have created a gallery-like space to display and sell their gorgeous wooden bowls. Most impressively, Andrew gathers entire logs in order to make use of practically all the material harvested. This store celebrates the artisanal efforts of both their on-site workshop and other small makers curated by the owners themselves.

Hall Art Foundation  – A contemporary art haven in the middle of bucolic Vermont. This museum juxtaposes its traditional barn structures with large outdoor sculptures and modern indoor pieces. Hall is open seasonally, from May through November on weekends and Wednesdays, by appointment. Booking a tour with one of the docents allows you a glimpse into the intricate stories behind each artist’s work.

Did we miss any of your favorites? Let us know in the comment section below.

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Kelby Cushman

Kelby Cushman is a writer and photographer in mountainous New Hampshire. As the original contributor for The Jackson House Inn’s blog in Woodstock VT, she found passion in telling the stories of farmers, chefs, and makers through words and images. Follow her adventures and photography on her website.


Kelby Cushman is a writer and photographer in mountainous New Hampshire. As the original contributor for The Jackson House Inn's blog in Woodstock VT, she found passion in telling the stories of farmers, chefs, and makers through words and images. Follow her adventures and photography on her website.

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