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A Winter Getaway to Woodstock, VT

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Vermont must be beautiful this time of year…all that snow!

One of my favorite perks of living in New Hampshire is being so close to many of our favorite destinations. Our neighbor, Vermont, may be most celebrated for her fall foliage, but winter in Woodstock is no less dazzling. So after a quiet January, David and I made our first trip of the year to a long-time bucket list destination: The Woodstock Inn in Woodstock, Vermont. 

Woodstock has been a popular getaway since 1793, when Richardson’s Tavern (a small pub with rooms) was first built in the very place that the Woodstock inn stands today.  In response to the tourism boom of the mid-19th century, the new Woodstock Inn was built on the tavern’s original site and was lauded for its grand facade and 100+ guest rooms.  The sprawling Inn quickly became the darling of visitors eager to take advantage of the property’s winter sports center and “riotous” winter parties – which were the talk of the town from Boston to Montreal. 

Despite temperatures in the teens we packed our trip with outdoor activities to make the most of the area’s beautiful state parks and skiing. Here’s a perfect wintery itinerary for 3 days and 2 nights:


Drive to Vermont and check in at The Woodstock Inn. After settling into your room grab a cocktail by the massive lobby fireplace before dinner at Richardson’s Tavern (where you will want to ask for a table by the fire again) then dive into a delicious meal starting with their famous fondue and a Vesper made with Vermont’s own Bar Hill Gin.


Brooks Brothers Camel Wrap Coat c/o (old, similar here, and here) // Everlane Cashmere Turtleneck // J.Crew Fairisle Sweater (old, similar here) // J.Crew Bobble Beanie // Mark Cross Benchley Bag (gray on sale!) // J.Crew Cashmere lined Leather Gloves 

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Outfit 1: Ralph Lauren Cashmere Cable Sweater // Emilia Wickstead Pants (last one!) // Gianvito Rossi Slingbacks (one left! brown version) // Monbouquette Earrings c/o  // Mark Cross Benchley Bag (gray on sale!) 

Outfit 2: J.Crew Cashmere Popover Jacket (old, similar here and less expensive here) // Talbots Denim Shirt // Everlane Cashmere Turtleneck  // J.Crew White Corduroy Pants (old, similar) // Pearl Earrings // Loeffler Randall Goldy Boots

Outfit 3: Sleepy Jones Silk Pajamas // Stubbs and Wootton Scalamandre Loafers c/o (get 20% off with “friendsofstacie”)

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Head downstairs for breakfast at Red Rooster before bundling up to tour the town. Woodstock’s architecture is beautifully preserved thanks to the Rockefellers’ generosity, and the shopping is good too.  F.H. Gillingham & Sons, a quintessential New England general store has been selling everything from snacks to hand-dipped candles, puzzles to flannels for over 130 years. I also loved poking my head into “Who is Sylvia” for vintage clothing. (I hope one of you bought that vintage Dior dress!) If you’re up for a short drive, Farmhouse Pottery and Simon Pearce’s glass blowing studio are both fabulous and just outside town. (We have lots of Simon Pearce glassware at home and love it!)

In the afternoon we rented snowshoes from the Inn’s activity center and drove out to Billings Farm, the launch point for a wonderful 3 mile loop through the Marsh-Billings-Rockefeller National Historical Park. Our route went up to The Pogue (Irish for “kiss”) then back via the “Road Less Traveled” trail – before finished up with hot chocolate at Billings Farm. There are other shorter and less challenging trails that the activity center can point out if you have kids in tow. 

We got back to our room with just enough time to warm up with a hot bath before dinner at  The Prince and the Pauper (5 min walk from the inn). Their 3 course prix-fix dinner is fabulous and we felt like we escaped to Europe for the evening. I recommend the duck and their Black Manhattan made with Averna, and call ahead to be seated in a booth.

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Outfit 1: Gloverall Plaid Coat (old, similar here)  // Molly Moorkamp Daphne Sweater //  Red Wool Knit Mittens // J.Crew Bobble Beanie (also own and love this one) // Sarah Flint Boots c/o (old, love these too) 

Outfit 2: Everlane Cashmere Turtleneck  // Dolce and Gabbana Plaid Skirt  // Loeffler Randall Goldy Boots // Tory Burch Belt (old, similar here)  // Haverhill Lang Studs c/o

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After breakfast in our room (blueberry pancakes please!) we suited up for a day of skiing at Suicide Six, notably the US’s first ski resort opened in 1934, and named for when the founder first saw the mountain face and quipped that to ski down “would be suicide”. Despite the name, it’s actually an easy-going mountain ideal for families or a relaxed day of skiing. The ski rentals were unexpectedly nice and after a few days of light snow we enjoyed powder-perfect conditions. 

Hungry from a day on the slopes we wandered into Worthy Kitchen for a bite before heading home! 

If you are traveling by private car it’s relatively easy to coordinate a trip to Vermont. As of the time of my writing you have two option: 1) quarantine in your home state for 14 days, or 2) quarantine for 7 days then take a test (with a negative result obviously!) – If you meet one of these requirement then you can mask up and enjoy your time in Vermont without additional quarantine requirements. Of course the guidelines can change so it’s always best to check before planning your trip.

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1 Comment

  1. Anna
    February 25, 2021 / 12:35 am

    Lovely post, thanks for sharing! I’ve added those pj’s to my wish list. <3

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