With a population of 12,000, Brattleboro is the largest municipality in Windham County, boasting a vibrant, walkable downtown and a thriving arts scene. Located just 10 miles north of the Massachusetts border on Interstate 91, the Connecticut River town has a rich history as a commercial hub and, in the early 20th century, as the reed organ manufacturing capital of the world.

Outdoor sightseeing and recreation opportunities include the iconic red Creamery Covered Bridge in West Brattleboro and nearby Fort Dummer State Park. A robust slate of festivals and programs — including the annual Brattleboro Winter Carnival, First Friday gallery walks and Northern Roots Traditional Music Festival — keeps things interesting year-round.

If you want to visit Brattleboro, Vermont, here's a suggested itinerary.

Note: Check websites to confirm business hours for the day you visit.

The Porch Café

This comfy-rustic breakfast and lunch spot a mile and a half north of downtown serves familiar favorites — customizable breakfast burritos, omelettes, waffles with local maple syrup — as well as rotating daily specials, such as birria tacos. Fuel up for a day of exploring with a bite and a lavender latte.
648 Putney Rd., Brattleboro

Brattleboro Museum & Art Center

Brattleboro is known for its eclectic arts scene. This museum, housed in a converted train depot, features rotating exhibits of contemporary art from Vermont and beyond. Works by well-known artists such as Andy Warhol and Chuck Close have graced the gallery walls, too. Kid-friendly programming includes the world’s longest-running domino-toppling event, an annual tradition since 2007. Exhibitions change every few months, so check the website in advance for a taste of what’s on view.
10 Vernon St., Brattleboro

The Estey Organ Museum

In the early 20th century, Brattleboro’s Estey Organ Co., founded by Jacob Estey, was the largest producer of reed organs in the world. The factory shuttered in 1960, but the company’s legacy lives on through the museum, housed in one of the Estey Co.’s slate-shingled buildings. Visitors can explore (and play!) the collection of historic reed, pipe and electronic organs.
108 Birge St., Brattleboro

Epsilon Spires

For lovers of the offbeat and highbrow, this nonprofit arts center in the former First Baptist Church hosts screenings of cult-classic films with accompanying live music, artist salons and other avant-garde fare. The crown jewel of this cultural sanctuary is its 1906 three-manual Estey pipe organ, one of the largest of its kind still used today.
190 Main St., Brattleboro

The Stone Church

From the outside, the Stone Church might look like your average — albeit awesomely Gothic — house of worship. But this Brattleboro landmark doesn’t hold prayer services. Instead, the Stone Church is one of the most rockin’ venues in Windham County. From Nashville bluegrass to electro-pop to psychedelic Afrobeat, this cathedral turned concert hall has a show for everyone.
210 Main St., Brattleboro

First Friday Gallery Walks

On the first Friday of every month from May through October, downtown Brattleboro becomes a full-on block party, with food trucks, art, live music and open galleries from 5 to 9 p.m. Browse handmade goods from local vendors at Brattleboro Flea, an open-air market that takes over Elliot Street during First Fridays in the warmer months. The event is rain or shine; in November and December, the festivities move indoors to the galleries.
Downtown Brattleboro; find a map of vendors and activities

Latchis Hotel

Located in the heart of Brattleboro within easy walking distance of shops and restaurants, this art deco hotel offers historic charm and modern amenities. While you’re there, be sure to catch a movie or performance in the grand, mural-adorned 750-seat Latchis Theatre, attached to the hotel. Pet-friendly rooms are available for travelers with four-legged friends.
50 Main St., Brattleboro

Echo Restaurant & Lounge

Across the street from the Latchis Hotel, Echo serves up small plates, brick-oven pizzas and other hearty eats in a cozy space. The cocktail-forward drink menu includes both tried-and-true stalwarts and more whimsical concoctions — Earl Grey martini, anyone?
69 Main St., Brattleboro