Our valley elevates community fun throughout the year.

Main Street Middletown hosts fundraising opportunities annually in order to continue supporting our area businesses and events. We celebrate our community, history, and culture.

Vintage Vehicles in the Valley

Downtown Middletown, Maryland 31 West Main Street, Middletown, MD

Experience the absolute fun walk down memory lane as Main Street Middletown partners with Warrior Canine Connection to bring all makes and models of vintage vehicles downtown on display along our historic National Road. From souped-up hot-rods to white-gloved exquisitely decadent cars of the 1920s...