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How to spend a cozy winter weekend in Middlebury, Vermont

By: The Outbound Collective + Save to a List

Middlebury is a charming small town in Western Vermont brimming with New England character. It’s an idyllic place for nature lovers and offers ample opportunities for hiking, biking, fly fishing, alpine and cross-country skiing, and wildlife watching. There’s no better place than the Northeast for a cozy winter weekend getaway!

Day one

Visit the Vermont Folklife Center

Learn about the communities and people who make Vermont special by visiting the Vermont Folklife Center. It was founded in 1984 and is an education and cultural research non-profit enhancing people’s understanding of Vermont’s diverse communities by documenting and sharing everyday expressions of tradition, innovation, and culture. Check the website for current or upcoming exhibits on all things local, from environmentalism and LGBTQIA+ pride to boxing and artisanal crafts. 

A close-up of an oval plate with sushi rolls. The rolls have an orange sauce drizzled on them and pickled ginger and wasabi sit at the back of the roll stack.
Photo from the Sabai Sabai Instagram

Lunch at Sabai Sabai

Savor an array of flavors at this traditional Thai and sushi restaurant. Get out of the cold and into this restaurant's relaxed and welcoming environment while enjoying pad see ew and Thai fried rice. Sabai Sabai offers a wide selection of poke rice bowls with names like the Green Mountain Bowl and the Rainbow Bowl. You know it’s a good spot when you see locals and college students dining next to you. They tend to know the best places!

Walk the Robert Frost Interpretive Trail

A snowy boardwalk curves off to the left before curving to the right into grove of snowy trees.
Photo from the National Forest Service

The famous American poet Robert Frost spent his summers in a cabin on a farm near Ripton, Vermont, from 1939 until he died in 1963. While in Vermont, Frost wrote and taught at Middlebury’s Bread Loaf Writers’ Conference and Bread Loaf School of English. This National Recreation Trail honors Frost’s poetry. While walking along this roughly 1-mile loop, you can read several of his poems on plaques alongside the trail. You'll get a real sense of what inspired his work while fully immersed in the woods and fields. The first 0.3 miles is along a boardwalk that is wheelchair accessible, leading to the South Branch of the Middlebury River.

Stop at Drop-In Brewing Company

Photo by Meritt Thomas

What’s a trip to Vermont without a stop at a brewery? This Middlebury brewery and tasting room will welcome you into a cheerful atmosphere with plenty of original and creative beers to go around! With names like “Dude, are you ok?” and “Dropinator” you’ll want to see (well, taste) what they’re all about. The tasting room is a fun experience as you’ll find a collection of brewery memorabilia on display from throughout the US. Grab a friend, grab a pint, and cheers to a memorable Vermont visit! Check out what’s on tap.

A from-above shot looking down at a snowy street with a large brick building that has many windows.
Photo from the Middlebury Inn Instagram

Stay at The Middlebury Inn

Stay overnight in the heart of Middlebury at this historic inn with Victorian-era charm that has been welcoming guests since 1827. The 71 rooms are furnished with antique decor aligned with the historical character of the building. The inn overlooks the village greens in the downtown area, meaning you’ll have easy access to the local boutiques and shops. In addition to the cozy rooms, the inn offers guests traditional afternoon tea and snacks on the veranda, plus cocktails and gourmet meals in Morgan’s Tavern. They also host live music! For some relaxation and self-care, book an appointment at the Waterfalls Day Spa for a massage or facial.

Day two

Breakfast at Middlebury Bagel and Deli

A bagle sandwich with bacon, red onion, tomato, and lettuce sits on a cutting board.
Photo from Middlebury Bagel and Deli

Carb up for your day at this family-owned and operated spot with homemade bagels! Order the bacon and onion quiche with a bagel or side salad. Or, try the tasty hot pastrami sandwich with Swiss cheese, red onion, and Dijon mustard on grilled bread. They also occasionally make donuts and other pastries - call ahead for insight into what's in the oven during your visit.

Hit the slopes at Middlebury College Snow Bowl

Photo by Patrick Hendry

The Snowbowl is right in the heart of the Green Mountains and is a local skiing favorite. Just 20 minutes away from Middlebury, this family-friendly ski area caters to visitors of all abilities with trails for beginners through well-seasoned experts. Ski and snowboard rentals are available. If you’re interested in cross-country skiing, snowshoeing, or fat-biking, the Rikert Outdoor Center is only a couple of miles down the road. It offers 55+ km of beautiful and ideal terrain for these winter activities.

Fuel up at American Flatbread

Photo from the Smerican Flatbread website

Head over to this Middlebury favorite after a day of chasing powder! Here, you can order a craft beer and delicious wood-fired pizza loaded up with an array of creative ingredients. All flatbread pizzas are baked in a primitive wood-fired earthen oven. This cooking method makes your meal come out light, crispy, and bursting with flavor! Choose from mouth-watering options like the “New Vermont Sausage,” the “Apple, Bacon, Cheddar,” and the “Free Form Flatbread”– any combination of anything you’d like!

Day three

Hike the Trail Around Middlebury (TAM)

A wooden boardwalk meanders through marshy green grass.
Photo by Josh Hummel

The Trail Around Middlebury, more commonly known as the “TAM,” is a 16-mile trail system made of existing parks, a ski area, and many private properties. Volunteers and workers come together to maintain and improve the trails so community members and visitors may enjoy the TAM. Visitors should follow Leave No Trace guidelines to protect this local treasure. You can choose from many scenic routes like the Middlebury College Trails, the Jackson Trail, and Otter Creek Gorge Preserve Trail. Some trails are bike and stroller accessible. There are also opportunities for cross-country skiing and wildlife viewing. Take your time, and you might spot some interesting animal tracks in the snow, like deer hoof prints!

Pro tip: Download the Outbound App to upload pictures and leave a review to share your experience on the TAM!

Visit Werner Tree Farm

A person is standing in front of a large red barn. They are holding the reins for two large brown and white horses who are wearing holiday wreaths around their necks. There is some snow on the ground.
Photo from Werner Tree Farm

Get into the holiday spirit by spending an afternoon at this family-owned tree farm that’s been growing Christmas trees for over 40 years. This solar-powered company believes in smart farming practices. After blissfully breathing in the fresh Christmas tree scents while browsing outside, head inside the cozy gift shop! Take home a farm-made wreath, centerpiece, garland, or locally-made maple syrup and honey! You’ll feel like you’ve been transported to a section of Santa’s workshop! 

With Vermont’s ample outdoor recreational activities, crisp air, welcoming family-owned shops, historic and outdoorsy-rustic atmosphere, it’s sure to be the cozy cold-weather getaway you’ve been dreaming of!

Cover photo: Kristaps Ungurs

We want to acknowledge and thank the past, present, and future generations of all Native Nations and Indigenous Peoples whose ancestral lands we travel, explore, and play on. Always practice Leave No Trace ethics on your adventures and follow local regulations. Please explore responsibly!

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