Have you heard of Woodstock, Vermont? It’s this gem of a small town located right in the middle of the state.

Conde Nast Traveler has called Woodstock, VT, one of the most beautiful towns in America, and since it was just a little over an hour away, we decided to make a day of it. My Mom had flown into Vermont to spend Christmas with us, and we were looking for a fun, post-holiday excursion. So we got up early, grabbed coffee and doughnuts to go, and headed over to what was one of the most charming towns I’ve ever seen. (Even the drive was gorgeous.)

A Charming Winter Day Trip: Woodstock, Vermont

Woodstock boasts an adorable little downtown filled with local boutiques, art galleries, gift shops, restaurants and one of the best (most well-edited) bookstores I’ve ever seen. Happily, they’re mostly local shops, completely unique to Woodstock. If nothing else, wandering around Woodstock’s downtown is worth a trip.

Woodstock also boasts four covered bridges (they’re just as quaint and picturesque as they sound), as well as plenty of stone walkways and pretty river views. We were so charmed by our ‘day’ trip, that we stayed well into evening.

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Where To Browse & Shop In Downtown Woodstock

Here are a few of our favorite places to explore in downtown Woodstock. These are the places that we — even the boys — spent quite some time investigating.

F.H. Gillingham & Sons – An old-fashioned general store that has been owned by the same family since 1886. They’ve managed to retain their old-world sensibility while stocking locally made products along with modern conveniences. (And in the back, they sell toys, hats, etc.,)

Yankee Bookshop – They’ve been open since 1935 (Vermont’s longest-running independent bookstore), and has, quite possibly, the most well-edited selection of books I’ve seen. We happily browsed in here for hours.

Woody’s Mercantile – This shop is a joy to browse; even the boys were into it. (Pax came home with a gold candle-lighter that uses a laser??) In addition to seriously cool home goods, they also have some jewelry and those faux-fur OverEasy hoodies I love so much.

Clover Gift Shop – Another really fun shop. In addition to clever little finds, this one also has stellar knitwear (hats, mittens, etc.,) and all kinds of little surprises. I grabbed a few fun things for Raines’ birthday.

Vermont Flannel Co – Family-owned, and everything is handcrafted in the US out of 100% organic cotton flannel. The range of plaids is staggering. This company has locations all over VT, but the one in Woodstock is very charming.

Farro Jewelers – The estate jewelry was really fun to browse (at least for me).

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Where To Eat In Woodstock, Vermont

We visited Woodstock the Monday after Christmas…which meant that many of their restaurants were closed (and frankly, we love the Vermont commitment to a good life-work balance). That said, we found plenty of places to grab a little treat.

Maple peanut brittle – In addition to locally made maple syrup, F.H. Gillingham & Sons also sells maple peanut brittle. It’s addictive, and we polished off a box so quickly we ended up going back for more.

Woodstock Scoops – For fresh doughnuts and a maple creemee (aka locally made softserve) head over to Woodstock Scoops. Cold? Yup. Worth it? Definitely.

Mon Vert Cafe – This place was so packed, we couldn’t get in. But their breakfast menu looked (and smelled — sob!) delicious. We’ve heard their breakfast sandwiches are NOT to be missed.

Abracadabra Coffee – Open only on weekends, but good coffee and good vibes.

Coburn’s Tonic – This place was short-staffed (like everywhere these days), but the rubens, lobster rolls and beer were great. A perfect spot to relax after wandering around.

Worthy Kitchen – Craft beer and farm-to-table…aka the place we’ll go next time we’re in town.

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What To Do In Woodstock, Vermont (In Winter)

This is by no means an exhaustive list…but there were a few things I can personally recommend, as well as a few additional activities that are on our must-do list for next time. And by ‘next time’ I mean a full weekend.

Wander the downtown – as I mentioned above, the downtown is a gem, especially in the winter, with snow-covered boughs and lights twinkling everywhere. And since the locally owned shop game is strong in Woodstock, the whole experience is just enchanting.

Visit an art gallery – Downtown Woodstock has a number of cool art galleries, but we loved the photography at Focus Vermont.

Billings Farm – They have sleigh rides, snowshoeing, farm activities (meet the cows, sheep, etc.,), and various workshops out at Billings Farm & Museum. Our mistake was heading to the downtown first. We ended up having so much fun that we missed the farm visiting hours. Next time, for sure.

Downhill Skiing (or Snowboarding) – Not only does Woodstock have it’s own ski area, Suicide Six, but Woodstock is also only 30 minutes from Killington (the biggest ski resort on the East Coast). There are also some seriously lovely ski-and-stay packages for The Woodstock Inn & Suicide Six.

Nordic Skiing, Snowshoing, Fat Biking – Woodstock’s Nordic Center has a network of trails for cross-country skiing, snowshoeing or fat biking. The Woodstock Inn has a whole slew of rentals and lessons available to make things really easy.

Explore the covered bridges – Woodstock is located along a river, and has several charming bridges spanning the river. Four of these bridges are covered bridges, with Middle Bridge being (arguably) the most photographed. This one is located riiiight downtown, and is definitely worth a wander, especially at night.

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Where to Stay In Woodstock, Vermont

Next time we come in for an entire weekend (or even just an overnight), I’m hoping to stay at the Woodstock Inn. It’s located steps from that seriously cute downtown, steps from middle bridge, and they have some pretty epic ski (or nordic ski) packages. Besides, in the winter, it looks like this:

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What To Wear/ Pack For Woodstock, Vermont

Visiting Vermont in the winter is cold. Like…really, truly, Northern-Girl COLD. And since this is a fairly popular tourist destination, if you haven’t made reservations in advance for restaurants (I’m terrible about this), you may end up eating on-the-go, outside. Warm coats, hats and mittens are a must. Also, it’s snowy, slushy and (thanks to the salt on the road) kind of messy, too. So warm weather boots with a good grip were really appreciated. That said, because we were popping in-and-out of shops and restaurants, layers were key.

On me: parka (s) | jeans (27) | boots | hat | mittens | mask | bag

On Raines: coat (m) | jeans | boots | hat | mittens

I’m a cold-baby, so under my coat, I layered my jeans and this cashmere sweater over Halfdays baselayers. They’re comfy, warm, and the top is cute enough to double as a shirt.

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If you’re ever in the mood for some Hallmark-level winter charm, I highly recommend Woodstock, VT. It’s like a movie, and yet is so refreshingly real.

xo,

S