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  • Writer's pictureVTMAG


Updated: Mar 22, 2022



To reach Middlebury, follow the gentle curves of the Lake Champlain Byway through the open fields and rolling hills surrounding Route 74 North and Route 30 North. This treasured Vermont town is home to one of the state’s most celebrated colleges, as well as a vibrant cultural scene that includes numerous museums, breweries, restaurants, shops, and historic landmarks. After the recent completion of the momentous Middlebury Bridge & Rail Project, the centerpiece jewel of Addison County is back in form and better than ever! For a cultured and memorable Vermont getaway, head to Middlebury to enjoy the best of what Vermont’s Champlain Valley has to offer.



As you approach Middlebury on Route 30, you will see the Ralph Myhre Golf Course on your right. This picturesque 18-hole course is open to the public for tee time reservations during the warmer months and serves as the home course for the Middlebury Panthers men’s and women’s collegiate golf teams. After passing by Youngman Field at Alumni Stadium, and the Chip Kenyon ’85 Arena, you will come across the Middlebury College campus on your left. Founded in 1800 by Congregationalist Reverend Jeremiah Atwater, this esteemed liberal arts college is nationally known for its international studies and environmental studies programs, as well as its comprehensive language education programs and world-class science facilities.

Upon reaching downtown Middlebury, Route 30 transitions into Main Street. Make a right at the intersection of Main Street and Cross Street and proceed over the Cross Street Bridge. After crossing over Otter Creek, make a left on Court Street, and head north towards historic Court Square. Home to the former site of the original Addison County Courthouse, the square sits at a central location that connects Eastern and Southern Middlebury to the downtown area at Merchants Row and Main Street.

At the intersection of Court Square and Pleasant Street, you will find the elegant Middlebury Inn. Originally opened in 1827 as the Vermont Hotel, the Inn has undergone several significant renovations, and rebranded multiple times since its inaugural year. Tastefully restored guestrooms pay aesthetic tribute to the Inn’s storied past and feature timeless decorative elements such as brass fixtures and period moldings. The Inn’s most sumptuous and iconic suites can be found in the Inn’s Porter Mansion building, which boasts exquisite marble fireplaces, an enchanting curved staircase, and a finely-crafted leaded glass entrance. Travelers in search of a pampering respite should book an appointment at the Waterfalls Day Spa, which offers unique and exciting treatments such as CBD Pedicures and Deluxe HydraFacials. Check in, drop your bags, and take a moment to unwind and acclimate to the local



It’s time to go out and see the sights in Downtown Middlebury!

Head south on Pleasant Street from the entrance of the Middlebury Inn, and turn right onto Merchant’s Row. On your left, you will see the famous Town Hall Theater. In years past, the distinguished theater has played host to numerous cultural events and festivals, such as the Middlebury New Filmmakers Festival. (See Page 60). On your right, the “Middlebury to Her Soldiers” monument stands in the middle of a triangular park that separates Pleasant Street from Merchants Row. Sculpted by American artists Marshall Jones and Seward Jones, the monument pays a moving tribute to Middlebury’s infantrymen who fought for the Union in the Civil War.

After you come to the intersection of Merchants Row and Main Street, you will see the recently-restored St. Stephen’s Episcopal Church on your right. Steeped in rich New England history, this church is celebrated for its Gothic stone architecture. It is also well-known for its “Revere Bell,” which was cast by Paul Revere’s Boston-based firm, the Revere Copper Company, in the early 19th century. If you take a right at Main Street from Merchants Row and continue to where it intersects with Pleasant Street, you will find The Congregational Church of Middlebury. This magnificent Federal-style church features a galleried interior, groin vaults, a circular dome, and slender ionic columns. The church’s tower is supported by a telescoped timber frame, which played a pivotal role in its survival of an intense hurricane in 1950 that toppled the towers of nearly every other church in Addison County.

After relishing a close and intimate view of two of Vermont’s most celebrated religious landmarks, head back down Main Street to browse through the eclectic literary offerings of The Vermont Bookshop. Following your intellectual interlude, stop by Sweet Cecily and treat yourself to a distinctive and amusing selection from their thoughtfully-curated assortment of puzzles, clothing accessories, decorative home furnishings, and Vermont-made goods.


As the evening sun fades over the Champlain Valley’s meadows, it’s a perfect time to enjoy a tasty dinner at one of Middlebury’s favorite restaurants. Pizza connoisseurs will luxuriate in the ambrosial flavor of the wood-fired, all-natural artisan flatbread pies at American Flatbread on Maple Street and those with a longing for classic American Pub fare will flock to Fire & Ice Restaurant & Big Moose Pub on Seymour Street. With walls adorned in quirky memorabilia, this Middlebury mainstay is well known for its cheerful and rustic atmosphere. In the mood for a savory delicacy? Try their Slow Roasted Prime Rib. Discriminating herbivores will adore their seasonally-rotating vegetarian dishes, such as their Winter Risotto with Arborio Rice and Roasted Butternut Squash. For a sweet ending to an exceptional first evening in Middlebury, try their heavenly Flourless Chocolate Cake for dessert.


It’s time to rise and greet the day with an energizing breakfast, courtesy of Middlebury Bagel & Deli. Enjoy classic breakfast standbys such as waffles, blueberry pancakes, bagels with Lox, and donuts in a cheerful and relaxed environment. Before you go, grab some snacks for the road. You’ve got a full day of exploring ahead of you!


Now that you’ve enjoyed a satisfying breakfast bite, it’s time to stretch your legs and embark on a spirited adventure. Regardless of the season, visiting vacationers will find a bevy of tantalizing options for hiking, biking, and outdoor exploration in Middlebury and its surrounding towns. In the colder months, travelers can take Route 7 South and Route 125 East towards Ripton to enjoy a phenomenal range of winter sports activities.

Located only 20 minutes away from downtown Middlebury, the Rikert Nordic Center features over 55 kilometers of pristine terrain that is ideal for skate skiing, classic Nordic skiing, and fat biking. Just a few minutes further down Route 125, the Middlebury College Snow Bowl in Hancock offers family-friendly skiing in the heart of the Green Mountains. With three lifts and seventeen trails, it’s the perfect place for skiers and riders of all skill levels to enjoy a revitalizing run within convenient distance of Downtown Middlebury.

In the warmer months, Snake Mountain and Mount Moosalamoo provide unforgettable sweeping panoramic vistas for adventurous hikers. Mount Moosalamoo also features a fantastic 9-mile mountain biking trail network, and the Heart of Vermont Bikeways loops offer legendary riding opportunities for seasoned cyclists, many of which begin in and around Middlebury. Those in the mood for a more subdued and laid-back outdoor excursion will no doubt opt for a stroll on the Trail Around Middlebury. Maintained by the Middlebury Area Land Trust, this 16-mile walkable network is the perfect way to take in many of the gorgeous sights of central Addison County.

Travelers with more of an appetite for cultural exploration will surely spring at the chance to visit Middlebury’s museums. Located directly across from the Middlebury College Campus on Main Street, the Middlebury College Museum of Art features an extensive permanent collection of Asian, American, and European art pieces, which span a wide range of historical periods and styles. Further up Main Street, the Vermont Folklife Center offers a unique retrospective look at the state’s history through immersive multimedia exhibits. On Park Street, the Henry Sheldon Museum of Vermont History highlights the rich cultural heritage of the Green Mountain State through its permanent collection of historical artifacts, including the famous “Memorial Chair.” The chair was built by Sheldon himself from an eclectic assortment of historical wooden “relics,” which he amassed through years of dedicated collecting. Each spindle on the chair was crafted out of wood that Sheldon acquired from a different historical site or American region.

Once you have satisfactorily acquainted yourself with Middlebury’s cultural institutions, stop by one of Edgewater Gallery’s two downtown locations on Mill Street and Merchants Row to peruse a sophisticated selection of artistic works from local and independent artists, photographers, jewelers, sculptors, and potters.


Whether you spent your morning ambling down a breathtaking outdoor trail or a polished gallery corridor, you’ve surely worked up quite an appetite by now. Satiate your hunger with an appetizing lunchtime meal from one of Middlebury’s premier eateries. Lovers of Thai and Asian Fusion Cuisine will fawn over the flavorful selections at Sabai Sabai on Merchants Row. Craving something spicy? Bring on the heat with their Stir Fried Red Curry. For a dish that’s both smooth and scrumptious, give heir Pad Thai a try.

Fans of fast-casual Mexican Food will make a beeline to The Mad Taco for their diverse menu, which makes artful use of locally-sourced produce and ingredients. Carnivorous epicures will favor their Smoked Pork Belly Tacos, and selective vegetarians will dive into their palatable and plant-based Roasted Yam Tacos. In search of a tasty beverage to compliment your farm-to-table fiesta? Order up a Margarita de Casa, and toast to “la buena vida!” Your good times in Middlebury are just beginning.


What better time than Saturday afternoon for some well-deserved retail therapy at Middlebury’s Main Street shops? At Danforth Pewter, shoppers can choose from a broad array of flawlessly handcrafted metal ornaments, as well as barware, kitchenware, and their nationally-known Pewter Oil Lamps.

Interested in an outdoor expedition? Look no further than Green Mountain Adventures/Middlebury

Mountaineer. With a comprehensive selection of outdoor gear, clothing, and fishing equipment, this store is a one-stop-shop for anyone itching to explore the wild and open wilderness. Don’t know where to start? Not to worry! In the warmer months, Green Mountain Adventures offers guided hiking, climbing, paddling, and fly fishing tours that are perfect for vacationers of all levels of outdoor expertise.

Jewelry enthusiasts will revel in the timelessly captivating custom and vintage pieces available at Autumn Gold, and avid gamers will be spellbound by the selection of collectible cards and classic turn-based games at Tinker and Smithy Game Store. Looking to snag a stylish piece of Middlebury College memorabilia? Stop by Forth ‘N Goal Sports and lose yourself in their treasure trove of collegiate merchandise.

Consignment mavens in search of sustainable sartorial splendor should pay a visit to Buy Again Alley. This fashionably conscious nonprofit thrift boutique provides affordable and stylish clothing to the Middlebury community. In addition to the consignment services they offer, they accept donated clothing. By creating “first job” employment opportunities for Middlebury’s college and high school students, they affect positive change in the local community while providing a valuable service for community residents.

For a tempting taste of Middlebury’s locally-brewed and distilled beer, cider, or spirits, indulge your inner bon-vivant with a visit to Woodchuck Cider or Otter Creek Brewing on Exchange Street, Appalachian Gap Distillery on Mainelli Road, or Drop-In Brewing Company on U.S. Route 7 South. These local operations are a part of a of a larger Middlebury Tasting Trail, which also includes Windfall Orchard in Cornwall, and Lincoln Peak Vineyard in New Haven. (Be sure to drink responsibly and have a designated driver on your tour.)


What better way to reward yourself for a day well spent than with a divine dinner from Middlebury’s preeminent gourmet establishments? With menu selections that are compatible with a wide range of dietary considerations, the varied menu at Two Brothers Tavern on Main Street is perfect for diners of all tastes and preferences. Served on a potato bun with optional plant-based American-style cheese, the Beyond Burger is filling, hearty, and 100% vegan-friendly. Additional menu highlights include their namesake Two Brothers Burger, featuring a New England beef patty served on a toasty pretzel bun, and their Butternut Squash Quesadillas with Cabot Cheddar, chopped walnuts, and Chile-infused honey.

For fine-casual dining in a historic and enchanting setting, book a reservation at Jessica’s Restaurant at the Swift House Inn on Stewart Lane. Located in the home of 19th century historian and Vermont State Legislator Samuel Swift, Jessica’s seasonally-shifting menu incorporates fresh ingredients in their artfully prepared delicacies. Their ribeye steak with mashed potatoes and crispy leeks pairs nicely with a full bodied 2016 Rombauer Napa Cabernet, and their Mushroom Wellington is perfectly complimented by a Catena 2017 Mendoza Malbec, or a Bethel Heights 2013 Oregon Chardonnay. For a flavorful finale, try their Lemon Tart with fresh berries and whipped cream for dessert.


Wake up and smell the coffee with a rousing excursion to Haymaker Bun Company. This critically acclaimed bakery has garnered praise from culinary critics across the Green Mountain State for its delicious breakfast treats. Head Pastry Chef Caroline Corrente’s signature line of brioche bun breakfast desserts are made using local ingredients, spirits, and flour bases, and are available in classic sweet, chocolate, and savory flavor varieties. Celebrate the morning with a heavenly taste of light and airy pastry goodness, and get ready to make the most of your last day in Middlebury.


For a signature Vermont sightseeing experience, head north on Seymour Street towards the historic Pulp Mill Covered Bridge. Although historical consensus wavers around the actual build year of the bridge, it is estimated to have been built around the year 1850. After multiple renovations due to structural inconsistencies, the addition of an external walkway now allows pedestrian traffic to freely travel from the Middlebury side to the Weybridge side, and vice versa. In the warmer months, the University of Vermont (UVM) Morgan Horse Farm – which lies directly north of the Pulp Mill Covered Bridge in Weybridge – is an ideal destination for a family-friendly outing. Guided educational tours of the fully-functional horse farm highlight UVM’s equestrian program, which is dedicated to continual preservation efforts of the beautiful specialized Morgan Horse breed. Known for their compact and refined build, intelligence, courage, stamina, and vigor, the horses are one of the most legendary American horse breeds. For an additional Vermont Covered Bridge photo opportunity, visit the Halpin Covered Bridge in nearby New Haven.


It’s time for a final lunchtime feast! Head to Costello’s Market on Maple Street for a superbly-crafted sandwich. Patrons can either choose from a wide variety of pre-made options – such as the De Pasquale’s Favorite sandwich with prosciutto, provolone cheese, tomato, and lettuce – or opt instead to purchase their own cheeses and meats to bring home. For additional fresh and natural produce provided by a member-owned cooperative with ecologically sound business practices, head to Middlebury Natural Foods Co-Op. Notable highlights available for pickup from their deli department include their Butternut Lasagna and Quinoa Salad, as well as kitchen-made sweets and baked goods.

As your time in Middlebury draws to a close, head down to Vermont’s Own on Main Street for a charming souvenir of your Vermont vacation. With handcrafted jewelry, cutting boards, wool hats, and Vermont Maple Syrup, it’s the perfect place to find great Vermont-made gifts for family and friends!

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