A Weekend in Brattleboro, Vermont

With the prospect of fall foliage and apple cider on my mind, it was time to get out of the city and escape somewhere where I could hike through actual forests instead of crowds of Boston commuters. I scanned the map and put my finger on Brattleboro, Vermont, a little town only two hours from the city, and located in a state I had been anxious to cross of my list.

Just 10 miles from the Massachusetts border and a quick hop over the Connecticut River to New Hampshire, I worried that Brattleboro was not going to be as “Vermonty” as I hoped my first trip to Vermont would be. Would there be hippie thrift shops? Could I still get a maple syrup on everything? Would choosing not to venture deeper into the state hurt my chances of finally seeing a moose? Though I didn’t see any moose, I didn’t need to worry—Brattleboro was certainly more than “Vermonty” enough.

Brattleboro is a small town but a vibrant one, with some friendly faces. “Great day for photography!” a woman passing by commented on my camera. As a New Jersey native, casual friendliness like this always catches me off-guard, but I smiled and agreed with her, continuing my walk down Main Street.

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Downtown in Brattleboro, VT #vermont #bookstores #downtown

A post shared by Jamie Ditaranto (@jamieditaranto) on Oct 8, 2015 at 7:04am PDT

After passing art galleries, thrift stores, the downtown waterfall, and the local bead story “Beadnik,” it became clear that I had stumbled on the place where 1960s counter-culture had come to retire. Downtown Brattleboro is a fortress of originality—the kind of place guarded by the sorts of people who would throw up their arms in protest should a Starbucks or Walmart attempt to move in. In addition to Beadnik, there are five independent bookstores, three microbreweries, and dozens of cafes and restaurants that emphasize local ingredients.
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The beer is extremely local. All three microbreweries are in walking distance of downtown, so I headed for Hermit Thrush Brewery for a tasting. A startup company, Hermit Thrush is bringing back sour ales with its Belgian style beers. If you’ve never tried sour beer before, the taste can be shocking at first, but then surprisingly pleasant when paired with any variety of Vermont cheddar. The brews come in varying degrees of intensity to accommodate all tastes, from the mild Party Guy to the jarring Stickney Creek. If you ask for a tour of the brewing facility, you’ll see the dedication to combining historical brewing processes with eco-friendly technologies. The brewery, in the spirit of Brattleboro of course, doubles as an art gallery.

After exploring the town, it was time to travel up the road to Dummerston, where I had booked an Airbnb for my cozy mountain retreat. The listing advertised the company of two lovable Australian Shepherds and a constant smell of French pastries, as the host ran a bakery attached to the house, and when I arrived I was not disappointed. I’m still not sure which was more welcoming, the air that smelled like cookies or the dogs that rushed to greet me with wildly wagging tails.

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Whether or not I can play with dogs is a huge influencer in the type of Airbnb I choose. My host in Vermont was a very good boy. #fivestars #puppies #vermontlife

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A post shared by Jamie Ditaranto (@jamieditaranto) on Oct 7, 2015 at 1:20pm PDT

Driving even further down the road away from Brattleboro, I set out for the Williamsville Eatery on the recommendation of my host. What was once one of the longest-running general stores in Vermont (dating back to 1828) has been transformed into this energetic new restaurant. The ski-lodge inspired decor is cozy, and the open-kitchen design allows you to watch the chefs at work while you wait for a table. Seating can be limited, especially on a busy Saturday night. The Eatery has become a popular gathering place for locals to indulge on incredible tacos and brick-oven pizza made with ingredients from local farms. Williamsville is a small community with very little else to entertain travelers—unless you would like to mail a letter at the post office—but the Williamsville Eatery lights up the town and puts it on the map.

In the morning, I was pleased to see the clouds breaking and the sun shining through the trees. After a breakfast of fresh strawberries and still-warm croissants baked by my host, it was time to check out and set off on a short hike up Black Mountain. The trail can be accessed from different points along Black Mountain Road, which allows you to start off closer or farther away from the summit. The level of difficulty is up to you, but no matter which you choose you’ll wind up at the same spot overlooking a beautiful landscape of forest-covered hills and valleys just the foliage.

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Autumn is setting in! Look out for my Vermont photo essay this week on my blog. #foliage #happyfall

A post shared by Jamie Ditaranto (@jamieditaranto) on Oct 7, 2015 at 8:10am PDT

It’s always hard to walk away from good views, but it was time to be getting back to Boston. Before leaving, I stopped once more in Brattleboro to have lunch, and couldn’t help lingering to snap a few more photos and pick up some local cheese and apple cider at the Food Co-Op. My short visit to Vermont left me well-fed, refreshed, and already dreaming about exploring everything else the Green Mountain State has to offer.

More from Smarter Travel:

• Taking the Kids to Vermont for Foliage and More
• 10 Best Romantic Vermont Resorts and Hotels
• Top 10 Fall Foliage Drives Around the U.S.

Jamie Ditaranto is a writer and photographer who booked her Airbnb specifically so she could play with dogs and eat fresh pastries. Follow her on Twitter @jamieditaranto.

(Photo: Jamie Ditaranto)