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A Perfect Winter Weekend in Downtown Brattleboro VT

Winter in Brattleboro is a magical time, full of twinkling lights, festive window displays, and a robust calendar that will keep even the most gregarious extrovert engaged.

A collage of photos featuring a winter weekend in Brattleboro, Vt.
Ready for a perfect weekend in downtown Brattleboro?

There are concerts and theater performances, gallery openings and workshops, festivals and food — lots and lots of tasty food. Is that your tummy growling, or is it mine?

Downtown Brattleboro has so many options for winter adventures that sometimes it’s hard to know where to begin.

Fortunately, we live just an hour away from Brattleboro and love to visit in every season. We’ve finally created the perfect weekend itinerary for a winter getaway in Brattleboro, based on our December visit, hosted by Love Brattleboro VT.

Ready for an amazing winter weekend?

Downtown Brattleboro VT: At-A-Glance

Here’s a bite-sized snapshot of everything you need to know to plan your trip!

  • When to Go: December through March for all the winter goodness
  • Where to Stay: If you really want that the downtown Brattleboro experience, you’ll want to stay downtown. Check into the Latchis Hotel and walk just about everywhere!
  • How to get here: Driving your own car is easiest, but you don’t need a car to explore downtown. The nearest airports are either Hartford (BDL) or Albany (ALB), which are both about 65 miles from Brattleboro. Amtrak’s Vermonter travels to Brattleboro daily from NYC, Philadelphia, and Washington, D.C.
  • How to Get Around: Downtown Brattleboro is very walkable, but we have included a few things in this itinerary that require a car. Skip those things if you’ve come in on Amtrak’s Vermonter or if you just want a walking weekend.
  • Top 3 Highlights: Brattleboro Museum & Art Center, Brattleboro Winter Farmers Market, and brunch at A Vermont Table.
  • Before You Go: Check out the calendar of events at Downtown Brattleboro Alliance.

Stay at the Latchis Hotel in Downtown Brattleboro VT

The Latchis Hotel in Brattleboro Vermont at night with street and traffic lights surrounding.
The Latchis Hotel was built in 1938.

During our recent visit to downtown Brattleboro, we were fortunate to stay in the Purple Room at the Latchis Hotel, which welcomes guests with rooms that manage to be beautiful and unpretentious at the same time.

The Latchis has been welcoming guests to its beautiful Art Deco hotel for 85 years, and it has preserved the history and charm of a bygone era while providing guests with all the modern amenities and comforts you’ve come to expect.

Each historic room features unique decor and furnishings, a record player with access to a large vinyl library, and comfy beds with luxury linens. Choose between mountain or city views, or for more budget accommodations, forgo the view altogether.

Free coffee is available in the lobby, and all of downtown Brattleboro is right outside your door.

Day One: Explore Downtown Brattleboro VT

A mural with writing in script on a green background that says 'Vermont Welcomes You'.
Vermont Welcomes You!

From the Latchis Hotel, explore several blocks of distinctive shops and galleries, festive holiday decorations, and incredible restaurants. Take the afternoon/evening to get the lay of the land and poke around in the shops — many are open late on the weekends.

Here are some of the fun shops that we love to explore whenever we visit Brattleboro.

  • Twice Upon a Time: Taking second hand to the next level, with three floors of vintage clothing, furniture, jewelry, tools, and collectibles.
  • Penelope Wurr: A fun and quirky European gift shop featuring glassware, ornaments, hats, cards, and more.
  • Altiplano: Based in Brattleboro and Lake Atitlan, Guatemala, Altiplano is a boutique that works with cooperative groups and small family businesses to create innovative clothing, jewelry, bags, and home decor while supporting indigenous communities and the environment.
  • Turn it Up!: Specializing in new and used vinyl, CDs, DVDs, video games, and vintage memorabilia.
  • Cara Wolff Jewelry: Handmade and hand-finished jewelry by artist, Cara Wolff – created from natural and repurposed materials, and inspired by the beauty of the natural world.
  • Everyone’s Books: This family-owned independent bookstore offers a broad range of titles but specializes in books about the environment and social change.
  • Sam’s Outdoor Outfitter: Closing in early 2024, as of this writing, all full-price items are 25% off, and gear and clothing are both flying off the shelves. It’s worth stopping in before they close for good.

Dinner at Echo

Echo offers simple, sophisticated meals with a creative flair.

Feel like pub grub? The burgers are a full half-pound of Vermont grass-fed beef with all the fixins on a butter-griddled brioche roll. Throw in a side of sweet potato fries with bomb sauce for a hearty meal that is both delicious and decadent. Those sweet potato fries may be the best we’ve ever tried!

Pair your meal with one of Echo’s special cocktail creations, which are so much fun, and include many of the seasonal flavors winter is known for — orange, rosemary, chocolate, and cinnamon (plus whatever else the bartenders come up with).

Be sure to make reservations on the weekend, as it’s a popular spot for locals and visitors alike.

Echo is located on Main Street in downtown Brattleboro VT and is open Tuesday – Thursday: 4-8:30, Friday and Saturday: 4 – 9, and Sunday: 4-8.

Catch a Show at Latchis Theatre

Inside the Latchis Theatre in downtown Brattleboro.
Inside the Latchis Theatre in downtown Brattleboro

Did you know that there’s a beautiful Art Deco movie theater hiding out in downtown Brattleboro, VT? Connected to the Latchis Hotel, the Latchis Theatre first opened in September 1938, just a day after the Great New England Hurricane ripped through Vermont.

The Latchis was built by four brothers in honor of their father, Demetrius, who immigrated from Greece and sold fruit from a cart on the streets of Brattleboro in the early 1900s. The brothers hoped that the Art Deco design would match the grandeur and luxury of their father’s home country.

To further memorialize Greek heritage and culture, the brothers commissioned elaborate murals of Greek deities by renowned artist Louis Jambour for the main theater and installed Greek statues throughout the terrazzo-floored interior. This ‘Greco Deco’ style combines Greek traditions with the fashionable Art Deco style that was so popular when the theater was built.

Hebe, goddess of youth and cupbearer for Zeus, guards the entrance to the main hall, ‘blessing all who enter there with the ever-invigorating essence of art’. Murals of Greek myths adorn the theater, and zodiac signs look down from the ceiling.

There’s no doubt that movie dates hit differently at the Latchis Theatre, whether you’re catching a Hollywood blockbuster, an indie film, or a special event. You can even book the Latchis Theatre for your own private screening.

Day Two: Brattleboro Farmers’ Market, Beer, and Art

A little shopping, a bit of beer drinking, and a lot of yummy food! Here’s your perfect itinerary for day two in downtown Brattleboro VT.

Breakfast at The Works

This delightful bakery, cafe, and coffee shop on Main Street specializes in freshly baked bagels with Vermont-sourced cream cheese, but there is a huge menu to choose from. Grab a grain bowl, an egg sandwich, or a smoothie to fuel up for a full day of adventures.

The Works is a small New England chain that is dedicated to serving delicious, healthy meals at reasonable prices. They work to support local suppliers and buy sustainable products whenever possible.

Brattleboro Winter Farmers Market

When you think of a winter farmers’ market, are you picturing sad potatoes and soft turnips ready to be dumped into a soup pot, or maybe then compost bin? Then you obviously haven’t been to the Brattleboro Winter Farmers Market, which happens every Saturday between November and March, from 10 am to 2 pm.

I am a sucker for farmers’ markets in every season, but I’m also used to slim pickings for veggies during the winter. Not only was the winter vegetable selection at the Brattleboro market beyond this Vermonter’s comprehension, but there were gourmet mushrooms, duck sausages, sourdough breads, pottery, jewelry, and prepared foods.

If you are staying at the Latchis, you may want to drive out to the Brattleboro Winter Farmers Market so that you can pick up loads of goodies. It’s a 30-minute walk from downtown to the Winston Prouty Campus on Austine Drive.

Beer Tasting: Hermit Thrush Brewery

Tara sipping on a sour beer at Hermit Thrush Brewery in downtown Brattleboro VT.
Tasting a Hermit Thrush sour

Vermont continues to lead the country in breweries per capita, and no matter where you travel in the state, you’ll find distinctive styles, innovative flavors, and cozy tap rooms with all kinds of personality.

Hermit Thrush Brewery in Brattleboro wears its sour label like a badge of honor, beckoning to beer lovers with snappy marketing, and encouraging them to give their flavorful sour brews a go.

The fact that Hermit Thrush only brews flavorful sours means that they have developed a depth of flavor that pushes boundaries, puckers lips, and satisfies taste buds. We opted for the standard flight offering, which consisted of four beers — two kettle-soured and two barrel-aged.

My favorite was the Zingerbird, a fruity, kettle-soured pale ale featuring local ginger from Full Plate Farm and Scott Farm Orchard in Dummerston, VT, but the barrel-aged Rowdy Monk was a close second.

All of the Hermit Thrush sours are fermented with wild yeast and brewed using sustainable energy.

Hermit Thrush is located on High Street in downtown Brattleboro and is open Thursday to Monday, from 11 am to 7 pm (6 on Sundays).

Choose Your Own Adventure: Galleries Galore or a Hike at Retreat Farm

Afternoon beer tastings will either make you lazy or encourage you to walk off the haze, so we’re putting the afternoon in your hands. If you want to go the lazy route, wander around downtown, do a little window shopping, and check out some of Brattleboro’s amazing galleries.

Here are a few galleries we recommend:

  • Gallery in the Woods: Featuring beautiful jewelry, fine art, and whimsical gifts from Vermont and beyond, Gallery in the Woods has been a Brattleboro mainstay for 20 years.
  • Harmony Collective: A collection of 31 local artists showcasing their work in a beautiful setting.
  • Gallery 34 at River Gallery School of Art: This intimate community gallery space features monthly exhibits showcasing the artwork of established and emerging artists.
  • Mitchell•Giddings Fine Arts: A cutting-edge gallery featuring a diverse collection of innovative works from regional artists.

For a more active afternoon, head over to Retreat Farm and meander through field and forest on 10 miles of trails. This beautiful trail network is open year-round and can be accessed from five different trailheads just outside of downtown Brattleboro.

During our most recent visit, we hiked the 1.2-mile Woodland Interpretive Loop, which features signs throughout with interesting tidbits about the forest ecosystem. Add an extra mile if you decide to walk to Retreat Farm from downtown.

Here’s a Retreat Farm trail map that you can download or print.

Dinner: High Thai

Peanut Curry Noodles at High Thai.
Peanut Curry Noodles at High Thai

Yes, you can enjoy contemporary and authentic Thai cuisine in the heart of downtown Brattleboro. This spacious, light-filled eatery is both energetic and inviting, with friendly staff, a fantastic beer menu, and meals that delight the senses.

The Peanut Curry Noodles hits the palate with so many alluring flavors and, believe it or not, Thai food pairs really well with your favorite Vermont IPA. Expect huge portions, affordable prices, and friendly dining neighbors. It’s the perfect end to a busy day!

Day Three: More Food. More Art

There’s no doubt that food and art are good for the soul, so we’re going to go all in today.

Pastries and Coffee: Fire Arts Cafe

A few of the fantastic pastries available at Fire Arts Cafe

Wake up early and drive a few miles outside of downtown Brattleboro for the best French pastries this side of the Connecticut River. Fire Arts Cafe is a stunning bakery and coffee shop where you can start your morning with a buttery croissant and a rich maple latte. Or maybe a slice of quiche and a steaming mug of tea. Decisions, decisions!

When you’ve had your caffeine fix and your fill of flaky pastries, head next door to Fire Arts Vermont, a combination glass-blowing and ceramics studio, with a beautiful gallery featuring a colorful mix of ceramics and glass art.

After we ogled the art, which featured the work of dozens of gorgeous pieces by artists from the Vermont Glass Guild, we popped in on a glass ornament class, where kids and adults were playing with fire while dogs napped in the corner.

In the ceramic studio on the other side of the gallery, shelves and shelves of clay tiles lined every available surface. We learned how the wet clay is molded into three-dimensional tiles that eventually combine to form massive mosaics of trees, creatures, and intricate abstract designs.

We were excited to learn that we can come back and take a glassblowing or clay workshop here, and we’re already thinking about how we can incorporate it into our next trip to Brattleboro.

Brattleboro Museum & Art Center

Eric checking out the exhibits at Brattleboro Museum & Art Center.
Eric checking out the exhibits at Brattleboro Museum & Art Center

Located in the middle of downtown, Brattleboro Museum & Art Center (BMAC) is an unforgettable addition to the wealth of creativity on display all over Brattleboro. BMAC is a non-collecting contemporary art museum with six galleries that rotate exhibits every few months. That means you can keep coming back to see new things every time you visit.

One of our favorite exhibits during our recent visit was Aurora Robson: Human Nature Walk (on display until February 11, 2024). Imagine an entire room full of colorful sculptures and lyrical wall art made almost entirely out of reclaimed plastic.

The deeper we looked at these immersive installations, the longer we wanted to look at them. There are tiny forks intricately connected to shreds of bottles, and plastic caps dancing alongside colorful pipes and tubes.

After viewing Human Nature Walk, I see the potential for ‘useless plastic’ becoming a building block that sparks creativity and encourages deeper observation.

Admission to BMAC is currently free, courtesy of M&T Bank.

Sunday Brunch: A Vermont Table

While the words ‘farm to table’ are kind of thrown around these days, and can mean just about anything, a meal at A Vermont Table embodies the true meaning of a farm-fresh experience, with locally sourced, seasonal ingredients that are prepared with creativity and love.

Brunch at A Vermont Table is a divine experience.

Depending on the frequently changing menu, you can get a pile of French toasted brioche, topped with a slathering of maple syrup and fresh berries, OR a double-decker patty of northeast raised beef, Vermont cheddar, shaved onions, housemade brioche roll, and hand-cut chips.

A Vermont Table is open for dinner (which I can’t wait to try) on Monday from 4-8 pm, and Thursday – Saturday 5-9 pm. Sunday Brunch happens between 10 am and 2 pm.

More Things to Do in Vermont

Grab our five-page printable bucket list that includes all the best things to do in Vermont!

A Quick Itinerary for a Winter Weekend in Downtown Brattleboro VT

Hey, looking for more spots near Brattleboro to explore this winter? Here are some posts you should check out! Take a look:

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A collage of photos from Brattleboro Vermont in the winter.

Thanks to Love Brattleboro VT and all the local businesses for hosting our weekend getaway in Brattleboro!

Tara Schatz is a freelance writer and the founder and editor-in-chief of Vermont Explored and Back Road Ramblers, an American road trip blog. She is also the co-author of the 3rd edition of AMC’s Best Day Hikes in Vermont, released in May 2023, and the author of 100+ Wonderful Ways to Experience Vermont.