Brattleboro Vermont: Arts Oasis and Lively Small Town

Brattleboro Flea Market
Flea Market at the Downtown Brattleboro Gallery Walk. Megan Mentuck and Aysia Reed photos.

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 located in southern Vermont’s Windham county. Home to beautiful views of Vermont’s luscious green landscape, a rich art and music scene, and plenty of charming local eateries and establishments, Brattleboro, Vermont is a fine destination for a trip up north.

Ella from Yalla Vermont. Megan Mentuck Photos.
Ella Szutu from Yalla Vermont. Megan Mentuck Photos.

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 stockade 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 a variety of different 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 never lost touch with its quirky roots. Lesch told us about a variety of different 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 really something for everyone,” Lesch said.

Brattleboro Business: Vermont Vermouth

One of the most interesting things about the town of 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.

Kobe Shwayder from Vermont Vermouth. Megan Mentuck Photos.
Kobe Shwayder from Vermont Vermouth. Megan Mentuck Photos.

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

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

Currently, Vermont Vermouth has four flavors for sale.

“The flavors change with the seasons,” said Shwayder when we asked where he got his inspiration for the flavors from.

“Sweet and dry are the most traditional, while apple is popular during the fall season, and Sweet Vermouth is popular during the winter,” said Shwayder.

There is Boreas Sweet Vermouth, Zephyr Dry Vermouth, Harvest Apple Wine Specialty, and Thalia Rose Vermouth.

Distilled using locally sourced and fresh ingredients, each flavor offers a unique taste! If you’re in the area, make sure to grab a bottle for some delicious, locally sourced drinks.

Art found during our stroll through the Gallery Walk in downtown Brattleboro. Megan Mentuck Photos.
Art found during our stroll through the Gallery Walk in downtown Brattleboro. Megan Mentuck Photos.

A Brattleboro Gallery Walk

Yalla, Vermont, another great dining choice in Brattleboro VT.
Yalla, Vermont, another great dining choice in Brattleboro VT.

Shwayder is one of many people in the Brattleboro area who has 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 a single 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 the center of downtown, this spot was a perfect place to stop for some 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 some homemade Middle Eastern food and a conversation with the establishment owner, Zohar.

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

Zohar, the owner of Yalla Vermont, preparing food. Aysia Reed photos.
Zohar, the owner of Yalla Vermont, preparing food. Aysia Reed Photos.

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 not always planned on opening up a restaurant in the town. In the beginning, he sold his authentic and delicious food at the farmer’s market. However, once a week was not often enough for residents and 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 is a reflection of what he described as “family recipes tweaked along the way.”

The former Hotel Brooks is now a large building that is at the center of the town of Brattleboro, it burned down and was rebuilt in recent years.
The former Hotel Brooks is now a large building that is at the center of the town of Brattleboro, it burned down and was rebuilt in recent years.

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

During your weekend trip to Brattleboro, make sure to 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 stumbling upon the town of Brattleboro until she really felt at home somewhere.

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

While we talked with Szutu enjoying our coffee (from a barista who 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 that she spoke so highly of.

Ella from Yalla Vermont. Megan Mentuck Photos.
Ella from Yalla Vermont. Megan Mentuck Photos.

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.

Stroll of the heifers, Brattleboro, Vermont
Stroll of the heifers, Brattleboro, Vermont. Paul Shoul photo.

Farmer’s Market

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

Boasting a variety of locally sourced foods ranging from vegetables to maple syrup, the Brattleboro Farmers Market is definitely 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 lead down the main street festooned with flowers, and the town held a festival.

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

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

Masala Dosa

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

Dosa Kitchen Food truck in Brattleboro
Megan ordering from the Dosa Kitchen food truck.

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

Falafal from Yalla Vermont. Aysia Reed Photos.
Falafel from Yalla Vermont. Aysia Reed Photos.

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 own masala dosa, saying, “It’s just something special.”

An Afternoon in The Great Outdoors

Locals Janice, Britney, and Casey with Dosa Kitchen owner, Leda, and her chef, Lizzy. Aysia Reed photos. Brattleboro
Locals Janice, Britney, and Casey with Dosa Kitchen owner, Leda, and her chef, Lizzy.

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 located 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 all of this delicious food was being grown.

Food alongside the Connecticut River? we’re in!

River View with a Brew

After our outdoor adventures, we made our way to Whetstone Station Restaurant and Brewery. This riverside eatery has delectable pub food and outstanding craft beers. Some of their own craft beers include the Whetstoner Session IPA, Midnight VT Black IPA, Penguin Porter, and Born 2 Run Blood Orange Goose.

View from the top of the Harris Hill Ski Jump. Aysia Reed Photos.
View from the top of the Harris Hill Ski Jump.

Dinner by the Riverside

Whetstone Station Restaurant and Brewery. Brattleboro
Overhanging view at the Whetstone Station Restaurant and Brewery.

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

Those dining at Whetstone have the choice of eating 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 were able to wind down and relax to live jazz music at the Vermont Jazz Center.

Immanuel Wilkins Quartet at the Vermont Jazz Center. Aysia Reed photos. Brattleboro
Immanuel Wilkins Quartet at the Vermont Jazz Center. Aysia Reed photos.

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.

We were accompanied by many other audience members, 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

To kick off our Sunday morning, we took a relaxing drive down the Brattleboro backroads all the way to Walker Farm.

A lot of the locals we spoke with boasted about this farm, so we needed to check it out for ourselves.  Vermonters are very in love with farming and farmers, and the same was true here in Brattleboro. Farmers are local heros here!

The entrance to Walker Farm. Brattleboro.
The entrance to Walker Farm. Aysia Reed photos.


An endless amount of pots for planting. Aysia Reed photos. Brattleboro
An endless amount of pots for planting.

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

The rhododendron tunnel that leads to a stone walkway at the Vermont estate. Aysia Reed photos.
The rhododendron tunnel leads to a stone walkway at the Vermont estate.

Ever heard of the Jungle Book or Captains Courageous? I bet you have. Rudyard Kipling wrote these very stories at this Vermont estate while overlooking his blooming irises, his very own tennis courts and courtyard, and spectacular rhododendron tunnel.

IMG 7855
Megan inside the home that once belonged to Rudyard Kipling.

We took a walk through the tunnel ourselves, and we were blown away by the beauty.

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.


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

And when you plan your trip, make sure to check out KOA campgrounds. With options for RVs, tent camping, and even clean and air-conditioned cabins to stay in, it’s a great home base for your Brattleboro adventure!

Brattleboro: Not to Be Forgotten

The sense of community, warm welcomes, nature fun, the unforgettable art and music, and farm-fresh foods made the Brattleboro trip unalike 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 inspires you to stay.”

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

This trip was sponsored by #LoveBrattleboroVT  but the opinions are the author’s own. 

Aysia Reed

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