A Weekend in Woodstock, Vermont

It was December when we booked our two-night stay at The Shire in Woodstock, Vermont. One of the reasons we impulsively decided to go was the lack of snow in Eastern Massachusetts at that moment. In years’ past, we had at least gotten a base coat of around six inches by that time, but this year’s winter had brought nothing but warm days that felt like early spring, or bitterly cold hours of sunlight where even a minute outside made your extremities go numb. So we wanted the feeling of winter, true winter in New England, cold with snow or warmth with a snowpack — something that served as a visual cue that it was actually winter, one of our favorite times to be a resident in New England.

We had been meaning to get back to to this scenic, laid back, slower-paced Green Mountain state since the day we left almost three years ago. If you’ve been to Vermont, you know the feeling we’re talking about. That moment your car glides onto Route 89—the two lane highway which breaks off from 93 in Concord, New Hampshire and runs northwest to Burlington, Vermont—and you’re surrounded by mountains like Mt Kearsarge, you know that this state is different than the others surrounding it. Vermonters are genuine, friendly, empathetic, and passionate about their active lifestyle filled with great food, hoppy beer, and caring people. We learned that this passion is contagious, regardless of where you are in the state.

We decided to go up the weekend before Presidents Day and Valentine’s Day to try to avoid inflated room rates. We also agreed that Woodstock would be our destination, since it was only a 2.5 hour drive from Boston. For all intents and purpose, it took us close to four hours to get up there after work on Friday night. But a delicious, perfectly cooked meal at the Simon Pearce Flagship store made up for it.

The rest of our weekend was magical and full of quaint, simple adventures that couldn’t have been more perfect. Though we didn’t get to go snowshoeing or hiking in the snow due to the single digit temperatures that weekend, we got our fill of snow while walking around downtown Woodstock, driving along Route 4 to the Long Trail Brewery, and taking in the beauty of the covered bridges unique to this area. Keep reading for more details on our Weekend in Woodstock, Vermont!

A Weekend in Woodstock, Vermont

Key Pointers

  • Bring layers, lots and lots of layers. Nighttime temperatures can drop below zero and daytime temperatures sometimes barely crack freezing. Extra wool socks, fleece-lined leggings, flannel shirts, and cotton sweatshirts are musts. Don’t forget mittens, scarves, hats and some sturdy winter boots. They are are the best in the heaps of snow, messy slush, and mud.
  • If you want to experience all the charm that Woodstock has to offer, book a night or two at hotel or bed and breakfast within walking distance to downtown. It is truly one of the most beautiful towns we’ve seen with a beautiful mix of Georgian, Federalist, and Modernist architecture, so a stroll around town is a must.
  • Think beyond skiing! As non-skiers, we are always on the lookout for other outdoor winter activities to experience the winter-white landscape. This place has no shortage of options with snowshoeing, hiking, cross-country skiing, and even snowmobiling. If skiing is your thing, check out Suicide Six located right in Woodstock.
  • Talk to the locals! Waiting for a table at a crowded restaurant? Poking around local shops? Window shopping? Chat with the locals, Vermonters are the definitely the friendliest of all New Englanders and they will more than likely have some great tips of what is worth your time while in the area.

Where to Stay

With the intent of leaving our car at a central spot and walking to the nearest restaurants and shops, we booked a stay at The Shire, a no frill place offering basic rooms with scenic views that overlook the Ottauquechee River. This budget friendly place is also pet-friendly, if you can’t find a sitter for your furry friends.

Sunset from The Shire Woodstock Vermont

Where to Eat, Drink, and be Merry

  • Simon Pearce Flagship Store Restaurant: Talk about a view, this restaurant juts out and over the Ottauquechee River. It is a truly beautiful place to visit, and the food is also amazing. Seasonal dishes are always on the menu, the staff is welcoming and sweet, and you get to drink out of the beautiful Simon Pearce glassware. Be sure to splurge a little here if you’re looking for some top-notch cooking.
  • Soulfully Good Cafe: This whimsical eatery lives up to its name—great comfort food and coffee that touches your soul. Their pastries and freshly sourced cheeses creatively pay homage to Vermont and its residents.
  • Mon Vert Cafe: This large cafe serves some of the best coffee around. Not to mention that they are also sourcing all of their food ingredients from local farms, this place means business. Be sure to order and eat there; the upstairs eclectic dining area makes a great place to cozy up in a large chair for few before heading back out into the cold.
  • The Red Rooster at the Woodstock Inn: This restaurant was the perfect stop for a mid-afternoon cocktail. Located in the historic Woodstock Inn, this elegant establishment is a direct reflection on the family that started it all, the Rockefellers. This casual bar was the perfect pit stop during our window shopping around downtown. The craftsman, yet artisanal aesthetic, and friendly, yet professional staff made our drinks and grilled cheese that much more enjoyable.
  • Worthy Kitchen: In full transparency, this rustic establishment gets extremely busy and loud, attracting everyone from young couples and families to college students and high schoolers looking for a fun night away from their parents. But their large portions and variety of offerings made it worth it. Be sure to try the maple fried chicken and their creamy mac and cheese if you decide to check it out!

What to Do

  • Window Shop in Downtown Woodstock: With some of the cutest shops in the most diverse buildings, this activity can keep you occupied for hours. Some of our favorites were FH Gillingham & Sons General Store (this place is huge), The Vermont Flannel Co., and Unicorn.
  • Go on a Covered Bridge Excursion: This area is known as the town that has the most covered bridges, unofficially. Take the time and drive around to find them all. They may look similar, but the coastlines and towns they connect are all unique. For more information on our trip, check our our post here.
  • Long Trail Brewery: We loved the Stowe breweries when we were in Northern Vermont, but when in Woodstock, this place the best around. Their beer is a direct reflection of their brand: perfect after a day outside in the fresh Vermont air—light, but hoppy, and flavorful. Serving up great bar fare, this place was a scenic 20 minute drive from Woodstock, and we easily could’ve spent all day there chatting with the bartenders and hanging out by the fire.
  • Take an Unexpected Turn Down a Dirt Road: One of the most freeing parts of our trip was leaving the crowded town behind us to find some of the most beautiful farms, general stores, and homes nestled along one-way dirt roads. It was mesmerizing and liberating to be away from people, blasting music, and driving along roads that took you further from civilization, connecting us to the world around us. For cute end destinations, try the South Woodstock Country Store or Sleepy Hollow Farm.
Woodstock, Vermont winter weekend getaway in Vermont
Woodstock Vermont, Sleep Hollow Farm

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