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A Trip Down the Middlebury Tasting Trail in Vermont

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Middlebury is a small town in western Vermont where the craft food and drink scene is just as enticing as the scenery. In either direction, you’re surrounded by massive mountain ranges–with the mighty Adirondacks to the west, and the lush Green Mountains to the east. And while this tiny town that’s tucked between mountain ranges may be small, that hasn’t stopped it from becoming one of the coolest craft food and drink scenes in the Northeast, boasting seven breweries, distilleries, and wineries within a five mile radius–including Otter Creek Brewing, Stonecutter Sprits, Whistlepig Whiskey, Drop-in Brewing, Woodchuck Hard Cider, Appalachian Gap Distillery, and Lincoln Peak Winery.

Middlebury is five hours from New York City, passing through Connecticut and Massachusetts (both for about an hour) before arrival into Vermont. As soon as you cross the state line, you’re struck with what’s around you–but also what’s not. Billboards, neon signs, subdivisions, and roadside litter are nowhere in sight. Strict laws protect Vermont’s picturesque towns, greens, historic covered bridges and lush Green Mountains.

Where to Stay in Middlebury: This Garage Turned Two-Story Apartment via Airbnb

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Middlebury is a college town, so there’s no shortage of bed & breakfasts, hotels, and Airbnbs in the area for visiting parents and tourists. Denny and I booked a really unique Airbnb called “funky, cozy, cool garage apartment” just minutes from town in Weybridge. Downstairs, the two-story converted garage had a cozy living room with a gas stove; it also had a full kitchen, dining area, and Apple TV. The view out the big front windows is a gorgeous black barn.

Though it wasn’t a fully functioning farm, the chickens clucking outside our door each morning reminded us that we were in the countryside; a couple friendly cats and one solo duck were also part of the family. Speaking of family, the hosts Jennifer and Jack were super helpful in getting us acquainted with the region, helping us narrow our massive list of stuff to check out. Though the Airbnb is a little outside of town (about 10 minutes), this puts you closer to some other little towns in the area including Vergennes and Bristol–more on those towns below.

What to Do: A Trip Down the Middlebury Tasting Trail, and Exploring Town
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In downtown Middlebury, boutiques and restaurants are centered around Otter Creek, which drops a dramatic 18 feet to become Middlebury Falls in the center of town. You can easily spend a day popping into the vintage, design, and Vermont-themed shops around Main Street. Several businesses are even butted up to the falls with scenic overlooks, like Middlebury Chocolate, a craft chocolatier with several of tables inside that overlook the top of the falls. Another great shop is by the falls is Clementine, whose selection of home stuff, stationary, and handmade gifts is really thoughtful and beautifully put together.

The main draw here though is for the Middlebury Tasting Trail, which includes seven pitstops including three distilleries, two breweries, a cidery, and a winery. Even though they’re pretty close together–within five miles actually–you should plan on making a day of it to enjoy each of the experiences and different locations.

There’s seven locations on the actual trail, which is more than enough for a day of boozy fun. (By the way, if you’re picking a day to hit all seven, Saturday is the only day they’re all open.) The first and northern-most stop is Lincoln Peak Vineyard, where you can sample all five of their wines for $5. The scenery here is fantastic–enjoy a glass on their patio overlooking a pond. Next up, cider giant Woodchuck Hard Cider calls Middlebury their home. Take a self-guided tour through their facility then belly up to the bar for a free flight of 4 samples. After that, another flight is only $3, making it easy to try their 15+ rotating ciders.

Stonecutter Spirits is next on the trail, producing single barrel gin and small batch whiskey. Along with the beautiful facility and bar, the unique thing about Stonecutter is how they’re producing the gin–they’re aging it. By aging the gin in whiskey barrels for four months, the result is a harmony of flavors that can best be described as a whiskey drinker’s gin. The Single Barrel Gin is so dynamic, it’s easy to see how one could sip it on it’s own–sweet notes of cardamom, orange peel and soft oak balance with the luscious green tea, juniper and rose petals. Samples are free, and their cocktail menu, which changes monthly by theme, is fantastic.

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Appalachian Gap is practically next door to Stonecutter Spirits, producing whiskey, tequila, rum, coffee liqueur, and gin. Their small tasting room is staffed by the owner and head-distiller, where stories and samples are free. Next up, Otter Creek is a great brewery whose tasting room just reopened–and was designed by half the power-couple behind Stonecutter Spirits. Their bar and small restaurant not only serves great beer, but they also have a great food menu–and the only stop on the tasting trail offering full meals.

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The last two stops on the tasting trail are Whistle Pig Whiskey and Drop-In Brewing. Unfortunately, Whistle Pig was closed for tours and tastings (check their website for more info)–so we headed straight to the latter. The small brewery and tap room at Drop-In Brewing has seven beers, including four rotating taps. They do tastings, pints, and growler fills–a righteous place to end the trail. Beer lovers, see below for more breweries in the region that aren’t on the Middlebury trail!

Where to Eat In and Around Middlebury: More Beer, Pizza, and Farm to Table Goodness

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Middlebury not only has a great booze scene–it also has fantastic for food. Virtually every restaurant is farm-to-table; not because it’s a “scene” here, but rather, a way of life that hasn’t changed in ages.

For breakfast, our Airbnb did provide us with fresh eggs from their chickens–but we did manage to venture out. About 15 minutes from our Airbnb, we’d heard really good things from our friends at Stonecutter Spirits about Vergennes Laundry–it came recommended as one of their favorite places in the whole world! Everything is wood-fired, incredibly tempting and therefore really easy to over-order. Use caution (or, you know–don’t!) Throughout the space, stacks of wood accent the already beautiful rooms. The breakfast was indeed fantastic, though we had to fight for a seat as other people sat around. Arrive early or on the later side of breakfast to avoid crowds.

For lunch, many friends told us about Noonie’s Deli, which to us, was just a deli. We’re vegetarians though, so don’t pass it up if you’re looking for an easy lunch right in town. One sandwich was big enough for two people, and probably the perfect size to take down to the park and waterfall that are just steps from its front door.

american flatbread middleburyamerican flatbread pizza

For dinner, let’s begin with one of our favorite cuisines: pizza. Since Vermont is so well-known for its cheese, it’s no wonder all the pizza is so damn good. For a true local experience, try American Flatbread, a micro-chain with three locations in Vermont. Don’t let the words “chain restaurant” fool you though–each pizza is made with organic flour, tomatoes, and many organic & locally farmed meats, veggies, and cheese, which the restaurant sources from their network of local farmers. Our Airbnb hosts also tipped us off to some great food options in town, including The Lobby, where you can get hungry just by heading the food-themed quotes chalked onto the walls here. Part of the dining room hangs over the rushing water of the falls, completely immersing you into nature.

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Also fun for just a beer in town or your good standard pub fare are Fire & Ice and Two Brothers; they’re just a couple blocks from each other. At Fire & Ice, a truly unique atmosphere that’s like a Cracker Barrel on steroids; the many rooms are completely filled with antiques from floor to ceiling. It’s hard to choose a highlight here–the full boat in the salad bar area, or the 2nd largest moose head taxidermy in Vermont. At Two Brothers, grab a beer in their charismatic tavern, cozy dining room, or lower-level lounge. This is the locals hangout spot, and with live music on many nights, it’s your best bet for a late night on the town.

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Aside from all the great breweries and food in Middlebury, there’s even more within a stones throw. Three must-visits for beer lovers include a visit to Fiddlehead Brewing, Bobcat Cafe, and Foley Brothers. They’re all are about a half-hour in either direction from Middlebury, but totally worth the drive. Fiddlehead is probably the most familiar name, and is a tiny brewery with tastings, pints, and take-out growlers. The best part: Fifflehead is connected to a BYOB pizza place called Folino’s that lets you bring your growlers from next door. Finish your growler with dinner, then fill it back up before leaving–or return the growler to get your deposit back. Bobcat Cafe is another good one, offering up comfort food and pub fare, and their own beers along with other Vermont locals. It’s right at the foot of the Appalachian Gap, a really scenic overlook of the mountains on Route 17.

Last, one of our favorite finds in all of Vermont was Foley Brothers, a family-owned brewery whose tap room is in a little red barn in the middle of nowhere. On the scenic drive to the brewery, paved back roads turn into dirt roads, up and down hills, giving way to magical views of the Adirondacks–then finally, the barn. The drive is worth it–a diamond in the rough, this little tap room is a craft beer lovers dream come true. Try their samples, have a pint, then stock up on the crazy-good Vermont beer in their shop. The only catch–they close early, so plan your day around getting there before 5.

foley brothers brewery

We should warn you: If you go to Middlebury, we guarantee it’ll be the first of many trips to Vermont for you. Though it’s a bit further than our regular weekend destinations, the food, drinks, hotels and people are so worth it that we booked our second trip to Vermont just 3 days after getting home from our first. Part two of our Vermont series is coming soon–an epic roadtrip down Scenic Route 100, with pitstops at the best breweries, hotels, Airbnbs, taverns, restaurants, and secret beer stores Vermont has to offer.


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