Middlebury was the first town I ever visited in Vermont. I have a distinct memory of driving west on Route 125 out of town after a tour at the College. I had never seen so many gorgeous rolling hills, glistening with sunlight, in my life. At that point, I knew I would make Vermont home—at least for a short time—if Middlebury College would have me. Now more than 10 years later, I couldn’t imagine being anywhere else.

Although I have an on-again, off-again love affair with the town of Middlebury itself, the community is full of supportive, caring people I am grateful to call my neighbors. Some days when I have barely brushed my teeth in the morning, I may (slightly) cringe at the thought of seeing those same people in the Middlebury Co-op, as there’s no such thing as anonymity in our town of 8,500 residents. But then I realize that I’ve made my home here for the accepting community we’ve all contributed to, and the quality of life it offers us all.

Tips for Visiting Middlebury, Vermont

More than ever, Middlebury is becoming a day-trip destination for visitors to the Green Mountain State—and not just those who have a tie to the College. There is a lot to do and see with new businesses popping up regularly, contributing to the growth and prosperity of the town. Here are my top picks for exploring Middlebury like a local, from restaurants to lodging to must-see sights and must-do activities. Have other suggestions to offer? Comment below!

Best Restaurants in Middlebury, Vermont

Dining in Middlebury: Casual, Family-Friendly Restaurants

For families and couples alike, American Flatbread, Middlebury Hearth is at the top of my list for a Vermonty dining experience that won’t leave you feeling ripped off (just don’t buy the bowl of salad for ~$30 with cheese). The recently renovated bar is easily the best in town with a great selection of local beers and perfectly made cocktails; Barr Hill Gin and tonics and Rye Manhattans are a must, depending on the season. The ambiance is super casual with red-and-white checkered table clothes and folding chairs, all positioned around the wood fire that bakes the thin-crusted deliciousness that is American Flatbread pizza. Pepperoni & Peppers, Cheese & Herb and the Revolution are my three standbys.

Dining in Middlebury: Special Occasion Restaurants

I’d opt for Jessica’s at the Swift House Inn for a birthday or anniversary dinner. Although the decor is a tad dated, it’s a beautiful country Vermont inn with food that is always quite good (the duck entrée is the best in Vermont; the crab cakes and filet are another good choice). It’s also easy to get reservations at Jessica’s, and the wine list is the most extensive in Addison County. For a romantic dinner, ask for a table in the library. If Jessica’s isn’t an option, Tourterelle in New Haven is another good option.

Best Breakfast in Middlebury

One thing the town is missing in my mind is a good place for a sit-down breakfast. Middlebury Bagel & Deli has delicious donuts, and Otter Creek Bakery makes delicious baked goods and maple lattes, if you’re up for a breakfast on-the-go worth every one of the calories. (Get some of the vanilla meringue kisses for later… mmm!)

Best Sandwiches in Middlebury

Costello’s Market, located in the Marbleworks, isn’t the most wallet-friendly option for lunch, but it is one of the tastiest. Owners Carolyn and John will always greet you—a local or not—with a big, genuine smile. Order some sandwiches (De Pasquale’s Favorite, the Blackened Salmon Sub, the Sicilian and the Scarface are my faves) and picnic overlooking the Otter Creek Falls.

Lodging Options in Middlebury

Whether you’re a fan of staying at motels, hotels, bed and breakfasts, inns or prviate homes through Airbnb, there’s a lodging option for you in Middlebury. If you’re on a budget, I’d recommend the history Middlebury Inn‘s Carriage House for lower rates; you can’t beat the location right on the town green. The Swift House Inn would be my choice if you’ve budgeted a bit more for your visit; try to stay in the Swift Room for a classic Middlebury experience.

Activities in Middlebury

The Middlebury Tasting Trail—a way to highlight the surging number of breweries, distilleries and cidery in town—is a must for those who like to imbibe. The trail consists of Otter Creek Brewing, Appalachian Gap Distillery, Drop-in Brewery, Woodchuck Cider, Stonecutter Spirits and Lincoln Peak Winery. Drop-in and Lincoln Peak are outliers, but the others are within a mile of each other on Exchange Street in town. Just make sure you have a designated driver; our friendly police officers in town mean business!

The Middlebury Farmers’ Market isn’t the biggest market in the state, but it is a good chance to fine some local products and get a feel for the community. From cheesemongers to jewelry-makers to local egg purveyors and maple syrup makers, each vendor at the Farmers’ Market has a unique story and will want to share their passion with you. They also often samples for you to try. Don’t miss Good Companion Bakery for a wood-fired cinnamon bun or salted pretzel.

Walk down Main Street in Middlebury, over the falls and then wind your into Marbleworks and take the footbridge back into town. There are some beautiful photo opps of the Otter Creek Falls, and this short walking route will give you a chance to duck into some of the locally owned stores in town like Sweet Cecily (locally made art, jewelry and home goods) or Vermont’s Own Products (from local fudge to hot sauce to maple syrup and everything in between, all made in Vermont).

If you are hunting for locally made items, Danforth Pewter, Maple Landmark and Vermont Soap are all owned locally and are worth a visit.

Outdoor Recreation Activities in Middlebury

If you’re up for hiking, there are two beautiful hikes not far from downtown Middlebury; both are relatively low mileage but have views at the top that make the up-hill climb worth every step. Snake Mountain boasts views looking towards the Adirondack Mountains and Lake Champlain and is less than five miles up and back. The Abbey Pond Trail (my neighborhood hiking spot!) is about two miles up, but steeper than Snake Mountain; you’ll be greeted by waterfalls along the way and Abbey Pond herself at the top. Both are good options if you plan on eating (or drinking) your way through Middlebury.

If spotting a covered bridge is on your Vermont to-do list, there are two in Middlebury: the Pulp Mill Bridge, a two-way bridge that’s listed on the National Historic Registry) and the Halpin Covered Bridge, also known as the “High Bridge,” outside of town a few miles.

Where did your travels to Middlebury take you? Have other suggestions to offer for those traveling to Middlebury, Vermont? Comment below, and start the conversation!