This Hidden Vermont River Town Is Bursting with Fall Colors

Can Vermont have too many cute fall towns? Nah.

Brattleboro, VT is a leaf peeper's dream come true. | Structured Vision/Shutterstock
Brattleboro, VT is a leaf peeper's dream come true. | Structured Vision/Shutterstock

“Nobody knows all this is here,” a grey bearded man with a familiar voice says as he holds court in the middle of a woodworking shop.

“You stop at the Vermont Deli between November and April on a Sunday, and you can’t find a spot. People pay for their overpriced sloppy joes, they pee, and they leave. They have no idea all this is less than a mile down the road.”

“All this,” as radio personality and voice of Motel 6 Tom Bodett calls it, is the town of Brattleboro, Vermont. He’s standing in HatchSpace, a sort of co-working space for woodworkers, which Bodett opened in hopes of drawing people into an area for which he’s passionately appreciative.

The New England allure of Brattleboro is obvious as soon as you turn onto Main Street, a meandering drive lined with historic brick buildings and topped with a skyline of church steeples. Downtown is dotted with art galleries, food co-ops, breweries, and artisan co-working spaces. The surrounding hills are filled with fall colors and endless apple farms.

But little of it is known to those who breeze by on their way up Interstate 91 to Vermont’s chic northern towns. Lacking the leaf peeping crowds but overflowing with leaves to peep, Brattleboro makes for an immersive escape into the season.

It's 5 o'clock somewhere. | Whetstone Craft Beers at Whetstone Station

Take one of Vermont’s most scenic fall hikes, with beer at the bottom

The hills will be on fire in a couple of weeks, Ironman Leo tells me as we look out over Miner’s Ridge. Not a literal fire, mind you, but alive with the oranges, yellows, and reds of dying leaves. By month’s end, they’ll be completely ablaze.

Leo Marshall, an Ironman triathlete and former Marine, has hoofed us to the top of Wantastiquet Mountain: greater Brattleboro’s best vantage point for fall colors, where mountains stretch to the horizon and the river runs past it. Though Leo had us to the top in 40 minutes, the hike is usually an easy hour for most.

At the base of the trail, across the river, is Whetstone Station, the city’s best-known brewery and only spot for waterside dining. It’s also the rare bar where you can drink in two states at once, a fact Whetstone owner Tim Brady takes pride in.

Brady, one letter away from a noted New England icon, is a legend of his own. He splits his time between Brattleboro and Key West and easily fits in both places. He jovially walks me through his brewery’s lineup of beers as nearly everyone we encounter stops to say hello.

Whetstone is about the closest thing Brattleboro has to a tourist attraction, mostly because it’s the only restaurant on the water. But not one person takes a selfie with a beer on the state line. Well, no one besides me.

vermont town
Make sure to explore all the turns and corners—and shops!—in Brattleboro. | Alan Schein/The Image Bank/Getty Images

Go apple-picking in this mill town turned hippie enclave

Brattleboro was founded in 1753 along the Connecticut River and developed into a mill town, thanks mostly to its abundance of timber and proximity to a waterway. But because most early buildings were designed to have their rear loading docks on the river, downtown Brattleboro faces inland.

That resulted in a narrow Main Street that could have been pulled from the outskirts of London. The winding, uphill drive offers small shops around every literal corner and the excitement of seeing something different each time the street curves.

apple picking
At Scott Farm, you can go apple picking... Or you can learn how to make hard cider. | Scott Farm Orchard

Since the 1970s, Brattleboro and its agricultural environs have drawn hippies yearning to live off the land. The agricultural lifestyle is what attracted Simon Renault from the French region of Brittany. He dropped out of law school to work farms in Ireland and Oregon before settling in Brattleboro and now manages Scott Farm Orchard, a 571-acre apple enclave set in the rolling hills of nearby Dummerston.

The land Renault presides over is a fall-lover’s paradise, complete with classes in making hard cider, 130 varieties of heirloom apples unavailable in regular grocery stores, and gallons of the farm’s special apple-ginger cider. The stuff is like nature’s own intoxicating liquor.

Just across an idyllic creek sits The Stone Trust, where stoneworkers create art and teach about their craft. This makes Scott Farm the odd place where you can learn to make hard cider and build a stone wall in the same afternoon.

river garden marketplace
Comfort food and warming drinks are awaitin'. | River Garden Marketplace

Get cozy with downtown dinner and drinks

One of fall’s great joys is coming inside after a day in the crisp air. Downtown Brattleboro, with its glittering street lights and big-windowed restaurants, is the reward you long for in the cold.

For a warming beverage, hit Mocha Joe’s, a simple coffee shop with single-origin roasts from around the world. The Ethiopian brew is barely $2.50 and one of the best cups of coffee out there. For comfort food, the open, inviting dining room at Duo is the move. The restaurant fills your stomach with prosciutto wrapped potatoes and flat iron steak au poivre.

Atop Main Street you'll find the River Garden Marketplace, a space where you can sample a collection of over 50 craft beers, then peruse stalls from local artisans. The onsite fast-casual kitchen also switches themes every month. Stomach-warming schnitzel and potatoes are on the menu in October. November has a Thanksgiving theme.

If you’d rather order take-out and snuggle, grab some dumplings, noodles, and other Chinese street food from Cai’s Dim Sum, located inside an art gallery. Chef Cai’s makeshift kitchen sits within the C.X. Silver Gallery, all set inside an unassuming home. So it might be worth showing up a little early for your Chicken Box Abundance to peruse some provocative modern works.

Latchis Hotel
A hotel that is also a theater? Sign me up. | Latchis Hotel

Where to stay in Brattleboro

Hotel options in Brattleboro are limited but ideal for a more secluded experience. If you want to stay in the heart of downtown, opt for the Latchis Hotel. The city’s lone art-deco structure also houses the Latchis Theater, so you can walk from your hotel room, down a terrazzo staircase, and into the lobby of the cinema. The record players in each room and the views of the mountains are the best in Brattleboro.

For the classic, Vermont B&B experience, opt for the six-room Inn on Putney Road. The building was once home to the director of the Brattleboro Retreat, the town’s mental hospital. Now, it backs up to miles of the Retreat’s trail system, where you can hike deep into fall colors and back out for warm cider in the living room.

In a long weekend in Brattleboro, I didn’t meet another person from further away than New Hampshire. The place felt like an autumn unto its own. Full of apple cider and mashed sweet potatoes, I realized fall had taken over my body in less than three days. What a treat for all the lucky motorists who venture just a mile off the exit.

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Matt Meltzer is a freelance globetrotter and Thrillist contributor. Follow him: @meltrez1.