Vermont’s Counter-Culture Haven Has Art, Literature & a Parade with Flower-Wearing Cows

Brattleboro, Vermont

In Brattleboro, the hippies who came in the ’60s never left – they just opened businesses. Now their kids run farm-to-table restaurants and taprooms, while keeping the town’s mix of art galleries, music venues, and independent shops alive. It’s Vermont’s most authentic creative hub, minus the tourist-town polish.

Famous writers set their stories in Brattleboro’s streets and hills

The town’s unique atmosphere has inspired many authors over the years. H.P. Lovecraft placed his horror story “The Whisperer in Darkness” in the hills around Brattleboro. Archer Mayor’s detective Joe Gunther solves crimes throughout Vermont in more than 30 novels based in Brattleboro.

Jacob M. Appel’s stories in “Scouting for the Reaper” mainly happen here too. When you walk through town, you’re following the same paths as characters from these books, connecting you directly to the town’s creative history.

Harris Hill lets you watch ski jumpers fly

Built in 1922 by Fred Harris who started the Brattleboro Outing Club, this 90-meter Olympic-sized ski jump got a $600,000 makeover in 2009. Jumpers reach 60 mph before takeoff, with the longest jump being 104 meters (341 feet) set by Blaz Pavlic in 2020.

There are 209 steps from bottom to top, and they use special snowmaking equipment to ensure good conditions for the yearly February competitions. It’s one of only six jumps this size in the whole country.

A parade with the loveliest cows you’ll ever see

From 2002 to 2023, the Strolling of the Heifers parade brought up to 10,000 people to Brattleboro each year. Unlike Spain’s bull runs, this Vermont event had calm heifers wearing flowers walking through downtown.

The group behind it had a $600,000 yearly budget for farm programs and ranked states on local food availability. At its biggest, you’d see up to 100 heifers plus horses, goats, and alpacas, all while “The Heifers are Coming to Town!” by Alan Greenleaf played in the background.

Mingle with real circus performers

The New England Center for Circus Arts, started in 2007 by twin aerialists, moved into a custom-built 9,000-square-foot “Trapezium” in 2017 after raising $2.5 million. The building has 40-foot ceilings shaped to match how trapeze artists fly and includes a professional-grade trampoline, foam pit, and indoor flying trapeze.

You can learn everything from handstands to aerial silks here, no matter if you’re a toddler or grandparent. They put on public shows, including a yearly fundraiser with guest artists from around the world.

Nobel Prize winners helped start the local literary festival

The Brattleboro Literary Festival began in 2002 with Saul Bellow making his last public appearance. Since then, more than 400 authors have come, including winners of the Pulitzer Prize and National Book Award.

Brattleboro has been home to two Nobel winners—Rudyard Kipling (1907) and Saul Bellow (1976). Many books are set here, like H.P. Lovecraft’s “The Whisperer in Darkness” and all of Archer Mayor’s Joe Gunther detective novels that follow a Vermont policeman solving crimes.

Local brewers use wild yeast they found right in town

Brattleboro’s beer scene has changed a lot lately. Hermit Thrush Brewery, open from 2014 to 2023, made sour beers using wild yeast they gathered from around town. Their High Street brewery offered Belgian-style beers aged in old barrels from wineries and distilleries.

McNeill’s Brewery, one of Vermont’s oldest beer pubs (started 1991), sadly closed after a fire in 2022. You can still visit Whetstone Station for riverside dining with craft beers and great views across the water to both New Hampshire and Vermont.

All American black-and-white dairy cows are registered in Brattleboro

The Holstein Association in Brattleboro keeps track of every Holstein-Friesian cow in America. This is the world’s largest dairy breed registry and maintains detailed records on all these distinctive black-and-white cows.

Holsteins make more milk than any other breed and make up over 90% of dairy cows in the United States. The organization also helps farmers improve their herds through genetic testing and classification services, making sure the cows stay healthy and produce plenty of milk.

Covered bridges from the 1800s still stand around town

In Brattleboro, you’ll find three old covered bridges that have been around for more than 100 years. These wooden structures cross local streams and show off classic New England design.

The bridges were built with roofs to protect the wooden parts from rain and snow, helping them last longer. You can walk or drive through these pieces of history that connect you to Vermont’s past while providing great photo spots along scenic roads.

Vermont’s first settlement is now a beautiful park

Fort Dummer State Park, just outside downtown, covers 217 acres and marks where Vermont’s first European settlement was built in 1724. You can enjoy three hiking trails ranging from easy to moderate while taking in views of the Connecticut River Valley.

The park has 50 spots for tents or RVs and 10 lean-to shelters if you want to stay overnight. You’ll also find picnic areas, horseshoe pits, and volleyball courts. The park is open for camping from mid-May through Columbus Day weekend.

Art Deco fans can watch movies in a historic theater

The Latchis Hotel & Theatre, built in 1938, still shows movies and hosts live shows in one of only two Art Deco buildings left in Vermont. Inside, you’ll see Greek gods and myths carved into the walls and ceiling.

After a $550,000 renovation in 2003, the theater keeps its historic look while offering modern comforts. You can watch new movies surrounded by original chandeliers and decorative details. A non-profit group owns the Latchis to make sure this special place stays around for future visitors.

A former church now hosts concerts from folk to heavy metal

An old church reopened as a music venue in 2016, keeping its beautiful architecture while creating amazing acoustics. The former Sacred Heart Church still has its stained glass windows, wooden seats, and 28-foot ceiling that makes the sound incredible.

You can enjoy shows from quiet folk music to loud metal bands in this repurposed building. The venue fits about 400 people and sits at 210 Main Street, just a short walk from downtown restaurants and shops.

A restored pond offers peaceful hiking and fishing

Sweet Pond came back to life in 2019 when the Franklin Dam was fixed. This 18-acre pond sits in a 100-acre state park in nearby Guilford, just a quick drive from Brattleboro. You can walk the 1.5-mile trail that goes all the way around the pond, where you’ll see wildlife and peaceful forest views.

The pond allows canoes and kayaks (no motors) and fishing for bass, perch, and pickerel. You’ll find parking, picnic spots, and trail access for day use without any entrance fee.

Visiting Brattleboro, Vermont

Brattleboro sits in southeastern Vermont along the Connecticut River and you can get there easily from Interstate 91 using exits 1, 2, or 3.

Stop by the Welcome Center at 77 Flat Street, open daily 10am-5pm. For places to stay, try the historic Latchis Hotel downtown or nearby inns like the Chesterfield Inn.