Exploring the Heart of Downtown Brattleboro
August 26, 2022

Visit downtown Brattleboro and you’ll quickly find how the town embodies what Vermont represents: progressive values, a buy local mindset, and an unwavering commitment to the community.

The heart of downtown Brattleboro is Main Street, a busy but cozy, walkable section of Route 5 lined with small cafes, a beloved food co-op, a historic movie theatre, art galleries, and independently owned shops. Some Brattleboro Main Street businesses—including the Latchis Theatre and Sam’s Outdoor Outfitters—have been around since the 1930s.

Like most communities, downtown Brattleboro experienced ups and downs over the past several decades. Structure fires, empty storefronts, and economic downturns created challenges. But a statewide downtown program and the perseverance of local citizens helped shape Main Street in Brattleboro into the thriving, welcoming place it is today.

Visit Downtown Brattleboro and Main Street

-A bridge crossing the Connecticut River into Brattleboro (iStock photo).

With a population of about 12,000, Brattleboro is one of Vermont’s larger communities. It has more residents than Montpelier, but fewer than Burlington. Located on the Connecticut River just off Interstate 91, Brattleboro is an easy drive to Southern Vermont for anyone traveling from Boston, New York, or Hartford.

“Brattleboro is probably the most cosmopolitan small town around,” says Greg Worden, who moved to Brattleboro in 1972, worked as a reporter and editor for the Brattleboro Reformer, served on the town selectboard, and was involved in efforts to revitalize downtown Brattleboro.

Worden now owns Vermont Artisan Designs and the Kitchen Sync on Main Street with his wife, Suzy. “Brattleboro has always felt like home to me,” he says. “I had opportunities to leave over the years. And I’d think about it and say, ‘Well, I like it here.’”

Across the street from Worden’s gallery, American and Ukrainian flags wave in the wind above another storefront. Locals sip coffee at a turquoise table outside the newly reopened Amy’s Bakery Arts Café. A sedan with two kayaks strapped to its roof is stopped at a red light while parked cars from New York, Massachusetts, New Hampshire, and Vermont line Main Street.

Main Street in Brattleboro is no ordinary place. A high density of restaurants, coffee houses, jewelers, boutiques, and art galleries in a tight-knit area of roughly three blocks evokes an energized yet low-key vibe.

Brattleboro’s Back Story

-Main Street in Brattleboro in the mid-1800s (photo: UVM Landscape Change Program)

Brattleboro—spelled Brattleborough until 1888—was primarily a printing town in the 19th century. It was home to a woolen textile mill, paper mill, flour mill, a maker of papermaking machinery, a reed and pipe organs manufacturer, four printers, and two machine shops.

The town was also part of Vermont’s water cure treatment era in the 1840s and 1850s. That’s when curative springs sprang up in places like Brattleboro, Clarendon, Newbury, Tunbridge, Middletown, Highgate, Hardwick, and Woodstock.

Harriet Beecher Stowe traveled to Brattleboro in hopes that the springs would relieve her melancholia, a type of depression. But ultimately, the water cure craze was washed up by the late 1800s.

Later, in the early part of the 20^th century, a piece of land on the Connecticut River between Brattleboro and Hinsdale, N.H., was the center of entertainment for Brattleboro area residents. The island was the location of Brattleboro Island Park. featuring a grand pavilion, movie nights, and baseball games until the 1920s when the island severely flooded.

And long before the park, the mills, and the water cure springs, Brattleboro was the site of the first English settlement in Vermont, Fort Dummer. When engineers dammed the Connecticut River in the early 1900s, the original fort site slipped underwater. Today, an overlook on the one-mile Sunrise Trail at Fort Dummer State Park points out the original Fort Dummer site.

Things to Do in Downtown Brattleboro

Brattleboro’s arts and culture scene, progressive vibe, sense of community, and independence make Brattleboro a place worth visiting. Here are some suggested things to do in Brattleboro, Vermont.

Art, Music, and Culture

-Brattleboro Museum & Arts Center (courtesy photo)

Gallery Walk

Founded in 1995, Gallery Walk features downtown Brattleboro galleries, studios, creative spaces, cafes, and more through two guided tours. The Brattleboro Words Trail Tour explores nearby Words Trail sites (starts at 5 p.m. at 118 Elliot Street). The ArtSEE Tour is an interactive, docent-led gallery tour (starts at 6 p.m. outside Harmony Collective). Free; no registration is required. Gallery Walk is on the first Friday of each month between May and December. (Visit brattleboro.com)

Brattleboro Museum & Art Center

The Brattleboro Museum & Art Center is a contemporary art museum featuring rotating exhibitions, events, and educational programming. Upcoming offerings include the annual Domino Toppling Extravaganza, a felted gnome workshop, a four-month herbarium series, and a pop-up exhibit by ArtLords, an Afghan-led movement using art for social transformation. (10 Vernon St., Brattleboro; brattleboromuseum.org)

Estey Organ Museum

Estey made its mark around the globe by creating reed organs, pump organs, melodeons, and pipe organs. Manufactured by the Estey family in Brattleboro, Estey Organs could at one time be found on six continents. By the time it closed in 1960, the company had hand-crafted over 3,000 pipe organs and more than half a million reed organs.  The Estey Organ Museum, dedicated to the history and heritage of the Estey Organ Company, is open Saturdays between May and October. (108 Birge St., Brattleboro; esteyorganmuseum.org)

Vermont Artisan Designs

This Main Street gallery, owned by Greg and Suzy Worden, highlights pieces large and small—from jewelry, scarves, and pottery to sculptures, oil paintings, and hand-crafted furniture.  Vermont Artisan Designs features multiple floors of decorative and functional pieces created by new and established artists from Vermont and beyond. (106 Main St., Brattleboro; vtart.com)

Brattleboro Outdoors and Recreation

-Trails at Retreat Farm (courtesy photo)

West River Trail

The West River Trail’s Lower Section in Brattleboro and Dummerston is a three-mile path ideal for walking, birding, biking, snowshoeing, and skiing. And the West River Trail just might be Vermont’s oldest transportation path. In 1879, the West River Railroad between Brattleboro and South Londonderry was established. Not long after the railroad opened, it became known as “36 miles of trouble” for its dangerous, narrow, and winding route. Thanks to volunteers and the Friends of the West River Trail non-profit, the former railway is now a safe and scenic place to enjoy the outdoors. (Visit westrivertrail.org)

Brattleboro Outing Club

The Brattleboro Outing Club is one of the country’s oldest civic outdoor sports associations. The club was founded in 1922 by local sports enthusiast Fred Harris—creator of the Harris Hill Ski Jump—and offers rowing, cross-country skiing, paddling, and tennis. (Visit brattleborooutingclub.org)

Retreat Farm

A day at Retreat Farm is good for the soul. The farm’s historic barns and 10 miles of trails make it an easy place to recharge and reconnect with nature. Enjoy farm animals, musical performances, walking paths and trails, goat yoga sessions, and interpretive signs about the history and nature of the property. The farm’s Forest Playground, Storybook Walk, food trucks, and Grafton Village Cheese shop are icing on the cake. Open daily from dusk to dawn for free.  (45 Farmhouse Square, Brattleboro; retreatfarm.org)

Fort Dummer State Park

Fort Dummer State Park is named for Fort Dummer, the first permanent European settlement in Vermont. The Vermont state park overlooks the site of Fort Dummer, which flooded after the construction of the Vernon Dam on the Connecticut River in the early 1900s. The site, now underwater, can be seen from the northernmost scenic vista on the Sunrise Trail.

This Vermont state park includes 50 campsites for tents or RVs, ten lean-to shelters, and three short hiking trails: Sunrise Trail, Sunset Trail, and Broad Brook Trail. The remains of the 1800s-era Boyden Farm are along the Sunset Trail, including stone walls, a small shed, and a farmhouse.  (517 Old Guilford Rd., Brattleboro; vtstateparks.com/fortdummer)

Visit Downtown Brattleboro Restaurants and Breweries

Peter Haven’s Restaurant

Just off Main Street is the acclaimed Peter Haven’s, a longtime fixture in Brattleboro. Dine on everything from oysters and rainbow trout to duck breast and a hearty Vermont-raised burger prepared by chef Zachary Corbin. Enjoy cocktails, an extensive wine list, and draft beers in a cozy, elegant setting in the heart of downtown. (32 Elliot St., Brattleboro; peterhavens.com)

Amy’s Bakery and Arts Café

Owned by self-taught baker extraordinaire Amy Comerchero, Amy’s Bakery and Arts Café in downtown Brattleboro is a bakery and much more. The café offers a jam-packed menu and specials featuring delicious fare, including dilly chicken salad sandwiches, split pea soup, a kimchi melt, café au lait, buttery vanilla layer cake, and chocolate tortes. (113 Main St., Brattleboro; facebook.com/AmysBakeryArtsCafe)

T.J. Buckley’s

Its motto, “World-Class Food, Small Town Charm,” is as accurate as ever.

Located in a restored 1925 Worcester Dining Car, T.J. Buckley’s is a local favorite Brattleboro restaurant that serves up organic, local, seasonal, and foraged food prepared by chef-owner Michael Fuller. The menu changes weekly based on availability of local and fresh ingredients, all featuring a variety of outstanding fare, including meat, fish, poultry, vegetarian, and vegan and gluten-free options. (132 Elliot St., Brattleboro; tjbuckleysuptowndining.com)

Whetstone Station

At Whetstone Station, choose from the craft brewery’s IPAs, pilsners, lagers, amber ales, porters, or stouts. Enjoy brewed beers, burgers, salads, soups, sweets, and more. The Rooftop Bier Garten features live music and stellar views of the Connecticut River. (36 Bridge St. Brattleboro; whetstonebeer.com)

Hermit Thrush Brewery

Hermit Thrush Brewery—named after the official state bird of Vermont— focuses on New American Sours using 100 percent wild yeast. The brewery combines environmentally sustainable practices, including wood pellet boilers, with locally grown ingredients and age-old brewing processes. Pours and flights are available indoors and outdoors, plus beer to go. (29 High St., Suite 101C, Brattleboro; hermitthrushbrewery.com)

To learn more about downtown Brattleboro, visit Brattleboro.com

Happy Vermont Podcast: Main Street, Brattleboro

In this episode of Happy Vermont, Greg Worden and Amy Comerchero share why they call Brattleboro, Vermont home. You can find Happy Vermont on Spotify, Apple Podcasts, Amazon, iHeartRadio, Pandora, and Google Podcasts.