Middlesex, Vermont is a town in Washington County located northwest of Montpelier, and southeast of Waterbury, Vermont.

Through most of the nineteenth century and well into the mid-twentieth century, the primary economic activity was farming. Dairy farming, sheep herding (for wool), logging, orchards and maple sugaring have all been part of the town's economy. Following the end of World War II, the town slowly transitioned to becoming a place to live for people who worked elsewhere, mostly in Montpelier.

Some notable resident of Middlesex, Vermont include: Patrick Leahy, senior US Senator from Vermont; Scudder Parker, former state Senator and 2006 Demogratic nominee for Governor; Anthony Pollina, serial candidate for Governor; and Robert M. Fisher, 1928-2007, artist.