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How To Have the Perfect Winter Getaway in Woodstock, VT

One of my favorite Christmas gifts from Josh to date was a wheel workshop session at Farmhouse Pottery, which led us to Woodstock, VT for a winter weekend getaway. And even after more than a year, I still consider it to be one of the most storybook-perfect places we've visited.

If you're looking to escape to a quintessential small town with great restaurants, beautiful scenery, adorable shops and cafes, Woodstock should be high on your list. While we were walking around the town, we really got that Hallmark movie vibe, and also, felt a really strong sense of community. It quickly became one of our favorite places, if not our actual favorite, town in Vermont to visit, and we're itching to go back.

Until we can make it back, though, I'm so happy to share our recommendations for a perfect long weekend in Vermont.

We stayed for three nights total (Thursday - Sunday), and gasp! We actually didn't stay right in Woodstock. I'll be honest, we kind of regret that. We found a cute little inn that was about 25 minutes outside Woodstock, and while we enjoyed our stay, we both agreed that next time, we'd definitely stay right in Woodstock. We spent one full day exploring the town of Woodstock, one day at Killington and another day a combination of Woodstock town again, and the surrounding areas.

February/2019. This trip was our first-ever winter getaway, and it gave us a whole new appreciation for the season. It also inspired our Lake Placid winter escape to attempt skiing. We'd go back to Woodstock in the winter season in a heartbeat, but are also itching to visit in the fall.

We stayed at the Snapdragon Inn in Windsor, VT. We ended up choosing it because it has 5/5 stars on TripAdvisor, looked beautiful online and just seemed like a perfect, cozy getaway for the winter season. And it was definitely a beautiful place to stay. It has historical connections to Hemingway and F. Scott Fitzgerald, stunning original architecture and perfectly cozy rooms. But Windsor, we felt, just wasn't an exciting place to stay and fell a little flat for us. It's also off a main road in the town, and we could hear a decent amount of street traffic at night. On top of that, we found Woodstock to be the highlight of our trip, and we just wanted to spend all our time there, so the 25-minute drive each way became a little daunting each time. We'd recommend the Snapdragon Inn if you're just looking for a beautiful place to stay that's the focus of your trip. But, if your goal is to explore Woodstock, it's probably best to stay in Woodstock.

Really nice fireplace in our bedroom. 
I definitely used the clawfoot tub every night. Josh even used it!

Sitting room at the Snapdragon Inn.

Sitting room at the Snapdragon Inn.

Next time we visit, we'd love to stay at the On The River Inn, or, if our budget allows, The Woodstock Inn & Resort. The Woodstock Inn is smack dab in town, and you can walk to everything, but it's pretty pricey. The On The River Inn is just outside town, and sadly requires a car to get into town, but has such a cool modern farmhouse atmosphere that we're dying to try it out for ourselves next time we visit.

The Woodstock Inn & Resort is right in town, and looks amazing.

It's New England, so chances are, you drove here. But, on the off chance you flew in, you'll definitely need a car. Uber and Lyft also operate here.

Farmhouse Pottery
I'm going to do a whole separate post on our Farmhouse Pottery experience (Updated! you can read that here). But, even if you don't do a wheel workshop session, just popping in to admire the craftsmanship and heart that goes into these pieces is worth the stop. If a few miles outside town, so you'll want to drive there, but it's definitely worth it, especially if you love clean, simple but rustic aesthetics (which, obviously, is my jam).

Walk Around Town
The town of Woodstock is probably the most charming we've ever seen, and it had a lot to do with its community. You could just feel that the town was happy, collaborative with one another and was proud of its heart. The Town Crier board in the middle of the town square alone proves that, and made my little heart grow a few sizes. On top of that, Woodstock was hosting an ice carving competition that weekend, so right in front of the Woodstock Inn were a bunch of people creating artwork from blocks of ice, and everyone was stopping by to chat and watch them. It was really lovely.

I really wish our town had a Town Crier board.

The ice carving contest was the most charming thing I'd ever seen.

Even in late February, the Christmas decorations were in full swing!

All the shops and cafes you'll pass along the way will put a smile on your face. The general store is quintessential and will have everything you could need, quite a few nice little giftable shops, a flannel attire specialty store, coffee shops (one with the coolest bathroom I've ever seen!), and on top of that, everyone at every place we popped into was insanely friendly. Be sure to meander through the side streets and get lost, too!

Killington Ski Area
When we went on this trip, neither of us were skiers yet. But, we wanted to squeeze in one winter-y activity, so we chose to go snow tubing at Killington. It's only about 30 minutes from Woodstock, so of skiing isn't of interest to you, snow tubing is an easy and fun way to get outside for some fresh winter air. We really enjoyed our time there, and while there were quite a few kids, there were plenty of adults there, too, making us not feel so lame. And we never felt like we were inundated with people or had to wait around a lot to get down a tubing lane.

The snow tubing park at Killington.

Killington also has the Beast Coaster, which is a roller coaster with 1-person cars that takes you through the ski areas and through the trees. Josh and I both did it to end our day here, and we both liked it! It's expensive at $17 per person, so it's not something we'd do again. But, I'm glad we did it once, and it was a fun way to end a perfect winter day outdoors.

Riding up the hill during the first part of the Beast Coaster ride.

Well, Ski, Of Course
Vermont is obviously known as a ski destination, and this area is no exception. We often drove by a ski area called Suicide Six and we just loved watching everyone going down the hills. Later, after looking it up online, semi-inspired to try it for ourselves one day, we found it was highly rated, offered ski rentals, and had a mix of beginner and more advanced trails. If the whole ski resort thing isn't for you, this place might be a good option.

Walk To The Covered Bridge
One of the best photo opps in Woodstock is the beautiful little covered bridge, and it's walkable from town. In fact, it's right in town, and you can't miss it. The scenery won't get much more New England that this bridge, and there's a pedestrian path on it, so you can walk across it without worrying about traffic (because it's definitely used by cars to cross the river).

Watching the ice chunks float down the river was mesmerizing.
We actually spent a lot of time on the bridge just watching them go by.

Simon Pearce Flagship Store
I honestly didn't think I'd be super into this because glass decor isn't my thing. But, we ended up having some extra time one afternoon and decided to visit the flagship location in Quechee, VT, which is about 15 minutes outside Woodstock. I'm so glad we went because we ended up having a lot of fun. Even though it's right off a busy road, the grounds are lovely and it still feels like a destination. When you walk in, you'll see a bar on your left, which is beautiful, the store straight ahead and their highly rated farm-to-table restaurant to your right. The show room and shop is beautiful, and even though it's not my taste, I was kind of mesmerized by everything.

The store was impeccably merchandised and so beautiful.

Downstairs if a viewing area with glassblower artisans creating the pieces that would make their way up to the store. You can get pretty close, and even talk with them and ask questions. Through the back door of this area, you'll have access to a viewing deck of the river, and it's a really nice spot to take in before heading back inside. After witnessing the process of hand-blowing the glassware, I now have two "Woodstock" style red wine glasses on my wish list. They'll cost a nice chunk of change one day, but just having two for Josh and I to use for cozy nights in will bring back memories from our trip here.

Viewing area of the Simon Pearce artisans. 

They'll answer any questions you may have! We chatted with one gentleman for a few minutes,
and he told us it takes about 10 years to become a full-fledged artisan for Simon Pearce.

The back observation area of Simon Pearce has a great view of a covered bridge and the mill.

Woodstock has so many tempting restaurants that we honestly had such a hard time deciding where to eat. Even the local diners and little tiny coffee shops and cafes all seemed so delicious. We didn't have a single bad meal during our stay, and even had the best dining experience of our entire lives.

Lincoln Inn & Restaurant at the Covered Bridge
Oh man, you guys, this was the absolute best dining experience we've ever had. Like, ever. Of life. And it looks like everyone agrees because they have a 5-star rating on TripAdvisor with over 200 reviews (not 4.5 - 5!). I have so much to say about this experience that I plan to do a whole separate blog post dedicated to our evening here (coming soon!). Bottom line, if you're looking for a fine dining experience that's also intimate, creative, inviting and meticulously well executed, you'll want to book a table at the Lincoln Inn & Restaurant. It's also an inn (obviously), so if you a book a room here, your venture home after dinner won't be far!

Worthy Kitchen
For our first night, we decided to go casual and eat at Worthy Kitchen. They call themselves the Craft Beer & Farm Diner, and it's an order at the counter, find any available table type place. The rustic setting is really relaxing and comforting, and the food totally mimics that with its comfort food offerings. We went with the mac & cheese and veggie burger, and both were excellent. We also got the cookie skillet dessert, which was as good as it sounds, and left feeling so warm and happy.

Windsor Station Restaurant & Barroom
It's not in Woodstock, but since we were staying in Windsor, we really wanted to try this place out. And we loved it. While Woodstock has endless dining options, I still think this place is worth the drive to get here if you're staying in Woodstock. The restaurant is in the old Windsor train station, and so many of the original architectural elements are in tact, including the ticket window. The ambience was just really nice, and the food was also great.

Inside the Windsor Station Restaurant.

Mon Vert Cafe
We didn't get more than coffee and hot chocolate here while walking around town, but I really regret that because their salads, sandwiches and cookies all looked so, so good. I so wish I hadn't been full when we popped in! Definitely make it a point tp stop in here, and if you have the time, scoot to the bathroom because it's one of the coolest I've ever seen.

I think about this bathroom and wallpaper more than I'd care to admit.

That just barely scratches the surface of your restaurant options. It must be so hard to live in Woodstock because I feel like all the places are so good, you'll just want to keep going back, but then you're missing out on trying new places.


  1. I have only visited Vermont once but I left a piece of my heart there. I just love its picture perfect little towns.

  2. You and me both! How could you not, right!?