Adventure Town: 9 Reasons to Head to Middlebury

Story updated May 8, 2019.

May in Middlebury kicks off with one of the most beautiful half marathons in the state, the Sweetest Half Maple Run (May 5). This year, the folks at Vermont Sun are bringing a new half marathon to the beautiful Branbury State Park, called the Vermont Sun Half Marathon (May 19). The month ends with two of the toughest events in the East: the Endurance Society’s 888k trail run around the Moosalamoo National Recreation area called Infinitus (it starts May 23) and the four-gap, 104-mile sufferfest/bike ride known as the Gran Fondo (June 29).

But in the months between there are more things to do in and around town than there are hours in a day. Small wonder that last year Outside Magazine named Middlebury #11 on its list of the top 16 towns in the United States.

We’ll also share a few reasons why we chose to live and work here as well. 


Run the Trail Around Middlebury

A combination of single- and double-track, the Trail Around Middlebury, or TAM as locals call it, weaves for 19-miles through the Middlebury College campus, along the edge of the golf course, across open fields where cows or sheep may be grazing and through forested town parks: you would never guess you were just a mile or two from the center of this idyllic, college town of 8,000. One of the most scenic sections of the trail starts just north of town at the parking area for Wright Park and follows the Otter Creek as it plunges ferociously through a narrow gorge. While mountain bikes are allowed on many sections of the trail, some are closed to two-wheeled traffic so check with before heading out.


Explore Breadloaf Wilderness

If you drive up Route 125 you will come to a series of yellow colonial buildings, the Breadloaf Campus of Middlebury College, which houses its famed writers’ workshop as well as many other events all summer. But the mountains and trails surrounding the campus are part of the state’s largest wilderness area, Breadloaf Wilderness, that spans 25,237 acres along the spine of the Green Mountains from roughly Route 78 (Brandon) to Sugarbush’s Mount Ellen. Within this vast area you’ll find Robert Frost’s homestead (and an interpretive trail across Route 125) and, just adjacent, the Moosalamoo National Recreation Area. One popular hike starts at Brandon Gap and heads up to Horrid Cliffs; but the most popular trails are around Mount Moosalamoo, Lana Falls and Silver Lake.


Mountain Bike Chandler Ridge

There are not too many places where you can ride a ridgeline with views of one lake to the West (Lake Dunmore and, in the distance, Lake Champlain) and another to the East (Silver Lake). But a few years back, the Vermont Youth Conservation Corps in conjunction with the Vermont Mountain Biking Association, cut a trail in the Moosalamoo National Recreation Area that starts at the Silver Lake campground, then snakes south along this ridge before it drops down in winding singletrack to snake through the ferns and forests of Leicester Hollow for an 8.8 mile one-way ride. Stop for a dip in Silver Lake along the way or double back to your campsite. Other challenging mountain biking is on the Chipman Hill area of the TAM.


Canoes0259Camp by a Lake

With hike-to campsites tucked just feet from the water among the pines, Silver Lake in the Moosalamoo National Recreation area is one of the best-kept primitive camping secrets in the state. Wake up and fly-fish for trout, use the campsite as a base to explore the Moosalamoo NRA and spend the evening by the campfire listening to loons call back and forth. The campsite is a half-mile hike from the Goshen trailhead. If you’re looking for something with more facilities, Branbury State Park (just below and west of Silver Lake), has campsite and trailer parking right on the shores of Lake Dunmore. Pitch a tent, bring a canoe or boat, and head out across Lake Dunmore.


Road Ride Two Gaps

While Middlebury is a great starting point to roll west across the rolling farmland of Addison County, cyclists come from all over the East to ride the gaps to the west. A favorite 45-mile road loop starts in East Middlebury and heads up Route 125, past the Breadloaf Campus and the Middlebury Snow Bowl before crossing Middlebury Gap and returning via Routes 100 and 73 over Brandon Gap. However, with Route 125 under construction this spring,


fishing4692Catch a Trout

Addison County has some of the best-known trout streams in the state, including the New Haven, Otter Creek and Middlebury rivers, and spring is one of the best times to explore them. Head to Middlebury Mountaineer, downtown, to pick up flies and local advice from the experts there or hire a guide through Green Mountain Adventures. The Middlebury Mountaineer’s website also features periodic fishing reports.


Hike Inn to Inn

The classic Vermont inn is alive and well in Middlebury and its surrounding countryside. In fact, the inn the Bob Newhart show made famous in the 1970s is now the Waybury Inn and as charming as ever. You can start from there or, just up Route 125, at the renovated Chipman Inn in Ripton, and hike trails and forest roads to Blueberry Hill Inn in the Moosalamoo National Recreation Forest, and from there on to Brandon. helps set up self-guided tours with various itineraries and will transport your luggage.


Take the Tasting Tour

Back in Middlebury, in less than five miles, you could run past some of the best beverage producers in the state, including Lincoln Peak Vineyard, Woodchuck Cider’s tasting room, Stonecutter Distillers, Appalachian Gap Distillery, Otter Creek Brewing and Drop In brewers. Or, you could hop on a bus and let someone else be the designated driver. The Middlebury Tasting Tour offers five stops on guided tours May 11, 18 and 25. Tours are also available in June, on June 1, 8, 15 and 22. Or, get a friend to drive and go on your own. www.lincolnpeakvineyard.


Get Some Culture

Though Middlebury is a full-on sports town, its cerebral side is more than well-developed, thanks in part to the top-ranked college just up the hill. The Middlebury College Art Museum has extensive collections of Eastern and Western art as well as rotating exhibits (coming May 24, photographer James P. Blair’s images from his 35 years of traveling the world for the National Geographic Society) Edgewater Gallery on the town green showcases some of Vermont’s best contemporary artists and craftsmen and, just up the road, the Town Hall Theater puts on excellent live performances. Don’t miss the annual Opera Company of Middlebury production, which recruits top talent from around the country, in early June each year. This year’s event, Cendrillon, is being performed May 31 to June 8.  The four-act opera by Henri Cain is based on Perrault’s 1698 version of the Cinderella fairy tale and will be performed with a full orchestra in the Town Hall theater. Another don’t miss: the Henry Sheldon Museum of Vermont History which will be showcasing Glenn Eame’s (founder of Burlington’s Old Spokes Home) collection of vintage bicycles in an exhibit Pedaling Through History: 150 Years of the Bicycle that opens June 21. (Vermont Folklife Center.)

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