The Fredericksburg Agricultural Fair is one of the city’s oldest continuing traditions and is widely recognized as the oldest fair in Virginia and the United States. It was established in 1738, when the Virginia House of Burgesses authorized fairs in Fredericksburg for the sale of cattle, provisions, and merchandise. In its earliest years, the fair included not only agricultural trade but also entertainment such as theater performances and horse racing.

The fair was not held continuously. Records from the fair itself note interruptions from 1881 to 1886, and again for about 16 years beginning in the mid-1920s as the Depression-era farm economy struggled. The modern fair was revived through planning that began in 1948, and in 1949 it moved to its present site.

Today, the Fredericksburg Agricultural Fair is held at the Fredericksburg Fairgrounds, 2400 Airport Avenue, where the grounds continue to serve not only as the home of the annual fair but also as a year-round event venue.