Middlebury Vermont, settled after the Revolutionary War, is the largest community in Addison County and listed on the National Register of Historic Places. John Deere, inventor of the world's first steel moldboard plow, apprenticed at a blacksmith's shop in Middlebury, and there is a historic marker commemorating his achievement. Middlebury is home to the Henry Sheldon Museum of Vermont History and the internationally recognized Middlebury College, as well as Otter Creek, the longest river in Vermont.

In 2010, Yankee Magazine, listed several Vermont towns in their slideshow of "Top 25 Foliage Towns in New England," including Middlebury, Vermont!

Middlebury and Middlebury College host many events throughout the year, including the Vermont Symphony Orchestra Pops Concert and Fireworks and the week-long Festival on the Green.