Brattleboro, Vermont: Home to Delicious Food, Stunning Scenery, and  Rich Community

By Megan Mentuck and Aysia Reed

Brattleboro, Vermont, is a small town of around 12,000 souls in southern Vermont’s Windham County. Brattleboro, Vermont is a fine destination for a trip up north home to beautiful views of Vermont’s luscious green landscape, a rich art and music scene, and plenty of charming local eateries and establishments.

We arrived in Brattleboro on one of the summer’s first hot days in June and met Greg Lesch from the Brattleboro Chamber of Commerce and Bob Stevens, a local real estate developer in the area, to learn more about the town where we’d be spending for three days.

Friday: Exploring Brattleboro

Brattleboro: Now and Then

Brattleboro was once called Wantastiquet by the Abenaki tribe, who fought against the British while allied with the French in the 1700s.

A fort was built called Fort Dummer to be a blockhouse and fence in 1725.

The town was known later as Guilford. Relics of its past can still be seen in the historic downtown, where old buildings have been restored and repurposed to offer visitors various stores and restaurants to enjoy.

The town grew once people started taking notice of its unparalleled river access and opportunities for outdoor adventure. Fort Dummer today is a Vermont state park.

However, Brattleboro has always kept in touch with its quirky roots. Lesch told us about various events held in the town, ranging from a food truck roundup every Thursday in the summer to a big community Thanksgiving in the fall.

“There’s something for everyone,” Lesch said.

Brattleboro Business: Vermont Vermouth

One of the most exciting things about Brattleboro, Vermont, is its residents and their tight-knit community.

What we thought would be a quick trip and tasting at Vermont Vermouth turned into a fascinating conversation with Kobe Shwayder, a Brattleboro business owner who traded a profession in academia for one in a distillery.

Shwayder started out by loving cooking and baking. Over time, he started brewing beer and making his own spice blends, eventually leading him to a vermouth distillery.

With a passion for mixing and creating flavors, vermouth distillery quickly became a hobby for Shwayder and is now a career.

He makes different flavors of this alcohol that to most people only belongs in a martini….but there’s more!

A Brattleboro Gallery Walk

Shwayder is one of many people in the Brattleboro area with a knack for creativity. The town has a thriving art scene, which was on display during the Downtown Brattleboro Gallery Walk, which takes place on Fridays.

With art on display ranging from paintings to ceramics to artfully crafted birdhouses, each Brattleboro gallery was different, and there wasn’t one you wanted to miss! The compact town is easy to navigate, and the galleries are easy to find.

What’s for dinner?

After the Gallery Walk, we headed over to St. Elliot’s Fish & Chips for well…fish and chips! Located in downtown, this spot was a perfect place to stop for food before heading home for the night.

Saturday: Living Like a Local for a Day

Breakfast? Falafel!

The next morning, we woke up early to head over to Yalla, Vermont for homemade Middle Eastern food and a conversation with the establishment owner, Zohar.

Zohar is another Brattleboro resident who you want to get to know more about!

He greeted us with a warm welcome and told us his story about how and why he moved to Brattleboro from Israel after hiking the Appalachian Trail in 2001.

Yalla Vermont

Zohar had only sometimes planned on opening up a restaurant in the town. Initially, he sold his authentic and delicious food at the farmer’s market. However, once a week was not often enough for residents so, Zohar opened up Yalla, Vermont.

Since opening the restaurant, Zohar has had resounding success and support from his community.

With a variety of food to choose from on the menu ranging from hummus to pitas to falafels, Yalla Vermont’s food reflects what he described as “family recipes tweaked along the way.”

Zohar told me, “That’s the fun. That’s the festival of food!”

During your weekend trip to Brattleboro, could you stop by for some falafel?

Ella: From Nomad to Brattleboro Resident

After wolfing down our falafel, we went to Patio Coffee, where we chatted with Ella Szutu, a resident who recently settled down in Brattleboro after a life of traveling.

Szutu works with Zohar at Yalla Vermont and only recently moved into town. Before choosing Brattleboro, Szutu traveled for years and lived in big cities; however, it wasn’t until she stumbled upon the village of Brattleboro that she felt at home somewhere.

When asked what about Brattleboro made her feel at home, Szutu said, “It’s the people.”

While we talked with Szutu, enjoying our coffee (from a barista she knew by name) and looking out at views of the river, we really got a sense of what the town is like and the community she spoke so highly of.

When speaking about the sense of community, Szutu said something that stuck with us: “It’s not that we all just know each other in town, but that we care about one another,” she said.

Farmer’s Market

Shortly after our coffee and conversation with Szutu, we went to the Brattleboro Farmers Market.

Boasting a variety of locally sourced foods ranging from vegetables to maple syrup, the Brattleboro Farmers Market is a must-visit for anyone traveling to the area.

Brattleboro was famous for an annual event derived from a local institution: The strolling of the heifers, in which cows were led down the main street adorned with flowers, and the town held a festival.

Sadly, after Covid, the event was discontinued, despite its vast popularity.

After cooling down in the shade with some Farmers Market lemonades, we headed to Dosa Kitchen for lunch with some locals.

Masala Dosa

Dosa Kitchen is a food truck owned by Leda Scheintaub and her husband, Nash Patel. Their most famous dish we tried was the “masala dosa,” a food creation native to South India.

We pulled apart the crepe-like food and dunked it into flavorful dips while talking with a few Brattleboro locals, including Janice, who’s lived in Brattleboro since 2004 and bonded with Leda over a mutuality of being “foodies”.

We met Britney and Casey, a younger couple who moved to the area from St. Paul and own a chiropractic business in downtown Brattleboro; and Lizzy, a Brattleboro resident who grew up in Bogota, Columbia.

The food from Dosa Kitchen was delicious, and the company made it taste even better.

Each local had something different they loved about the town—whether it was the beautiful river views, access to outdoor recreation, thriving art scene, or some combination of the bunch.

Britney summed it up between bites of her masala dosa, saying, “It’s just something special.”

An Afternoon in The Great Outdoors

On Saturday afternoon, we spent our time exploring the greenery that surrounds the town. This included the acclaimed and historic Harris Hill Ski Jump.

This Olympic-sized ski jump was out of commission for the warmer months but offered us a great walk to the top via the 158 steps alongside it.

We also stopped by the West Dummerston Covered Bridge, where some people were cooling off in the river. Wild Carrot Farm wasn’t too far from there, so we stopped by to see where this delicious food was being grown.

Food alongside the Connecticut River? We’re in!

River View with a Brew

After our outdoor adventures, we went to Whetstone Station Restaurant and Brewery. This riverside eatery has delectable pub food and outstanding craft beers.

Dinner by the Riverside

Not only was the food next level- so was the view. It’s a spectacular setting on two floors; check out the upstairs area.

Those dining at Whetstone can eat inside with a view of the Connecticut River or outside on the deck.

A Jazzy Way to End the Night

Following our tasty dinner, we could wind down and relax to live jazz music at the Vermont Jazz Center.

We were honored to watch the  Immanuel Wilkins Quartet perform, which consisted of four ever-so-talented young musicians.

The venue is one of New England’s leading jazz centers and is home to many world-class jazz concerts.

Notable performers have included Sheila Jordan, Dave Liebman, and Kenny Barron.

Many other audience members accompanied us, and we were once again able to see how art and music had brought the community together as one.

People danced in their seats, swayed back and forth, and even played along to the music on their knees as if they were drumming in the quartet themselves.

Sunday: Scenic Surroundings and Farm Fun

Walker Farm

We took a relaxing drive down the Brattleboro backroads to Walker Farm to kick off our Sunday morning.

Many locals we spoke with boasted about this farm, so we needed to check it out ourselves.

Vermonters are very in love with farming and farmers; the same was true here in Brattleboro. Farmers are local heroes here!

As we strolled through, we felt like Brattleboro locals. Farmers working welcomed us with warm smiles, and endless rows of flowers greeted us around every corner.

At the center of the farm is a greenhouse overflowing with refreshing flowers and colorful plant pots.

The Brattleboro Marina

Strolling around the farm worked up our appetite for some lunch.

Around noon, we headed over to The Marina. The Marina is a picturesque restaurant right on the water. Kayakers and other boaters can enter the river here for a leisurely paddle.

We ordered burgers and enjoyed our meals while watching locals kayak and boat along.

A Flower Tunnel at a Vermont Estate

Full stomachs and ready for a drive, we set out to the Rhododendron Hedge Tour at Rudyard Kipling’s Naulakha.

Have you ever heard of The Jungle Book or Captains Courageous? I bet you have.

Rudyard Kipling wrote these stories at this Vermont estate while overlooking his blooming irises, tennis courts, courtyard, and spectacular rhododendron tunnel.

We walked through the tunnel ourselves, and the beauty blew us away.

The blooming flower tunnel leads you to a stone path with a view overlooking his green, flourishing front lawn.

The view captured the essence of the estate while also reminding us of the calming yet welcoming nature that Brattleboro has to offer.

Accommodations

What is our main takeaway from Brattleboro? It’s a must-visit!

Brattleboro: Not to Be Forgotten

The sense of community, warm welcomes, nature fun, unforgettable art and music, and farm-fresh foods made the Brattleboro trip unlike any other.

As Ella Szutu, the local we met in town, stated, “People here want community. The people have an open mentality that inspires you to create and stay.”

The nature, rich history of Brattleboro, and the tight-knit community of the locals made us never want to leave.

# LoveBrattleboroVT sponsored this trip, but the author’s opinions are theirs.