A Long Weekend in Middlebury



Train arrives at Middlebury station MBY, 30 Middle Seymour Street, Middlebury, VT 

Check in at the Swift House Inn, about an eight-minute walk from the station, or the Middlebury Inn, about ten minutes away on foot. Some activities in Middlebury are more conveniently accessible by car. Taxi services like Green Mountain Taxi and Middlebury Taxi make it easy to get around. Uber and Lyft operate in Middlebury, and Tri-Valley Transit operates buses around Middlebury with connections to the greater region. We recommend planning and calling for taxi pickups ahead of time.


Enjoy breakfast at Haymaker Bun Co., where ingredients for light, fluffy brioche are sourced as close to home as possible, or walk to the Middlebury Farmers Market, about 20 minutes away on foot, to enjoy fresh, local food and the sense of community that comes with meeting local farmers, artists, and growers.  From there, visit the Henry Sheldon Museum, the oldest community history museum in the country, exhibiting 19th and 20th century Vermont furniture, paintings, and household relics. (You can also take in an exhibit of curiosities on loan from 36 local collectors.) If you’re looking to get out in nature, rent bikes at Frog Hollow Bikes or strike out on foot. Go for a hike along Abbey Pond Trail, a 4.2-mile trail in the Green Mountain National Forest with a waterfall along the way. Finish the day with beers at Otter Creek Brewery and enjoy dinner at American Flatbread, where  pizza is cooked to order in an earthen oven.


Head to Morgan’s Tavern at the Middlebury Inn for a hearty breakfast before exploring the trails. The Moosalamoo Area Trails, encompassing 70 miles of preserved forest, Texas Falls, with waterfalls and gorges accessible for swimming, wading, and photography along the way, or the Trail Around Middlebury, a historic trail open to the public for hiking or biking, are great options for outdoor exploration. The literary-minded will appreciate the Robert Frost Interpretive Trail, a national trail commemorating the U.S. poet laureate most known for “Stopping By Woods on a Snowy Evening.” The trail features Frost’s poetry throughout. In the winter, the Middlebury Snow Bowl offers skiing and riding on 17 trails with three lifts.  Enjoy lunch at Mad Taco, known in Vermont for fine Mexican food, handcrafted hot sauces, and local beer, and then immerse yourself in Asian art, photography, contemporary art, and 19th-century sculpture displayed at the Middlebury College Museum of Art. End the day by tasting locally brewed honey mead at Golden Rule Mead, using honey from Vermont apiaries, dinner at Two Brothers Tavern, and a walk through Middlebury’s historic downtown or, enjoy a show at Middlebury’s Town Hall Theatre.


11:01 a.m.: Train leaves for NYC  

Prepare for the train ride home by grabbing juice and an acai bowl at Juice Amour or filling up at Middlebury Bagel and Deli. Finish your trip by stopping at locally owned shops to pick up a souvenir.

For more lodging, shopping, and dining in Middlebury, visit the directory.