Darien's Memorial Day Parade takes place annually on Memorial Day along the Boston Post Road between Brookside Avenue and Spring Grove Cemetery. The parade features many prominent Darien organizations, including boy and girl scout troops, veterans organizations, the high school marching band, and the town's three volunteer fire departments. 

The parade is usually followed immediately by EMS-Post 53's annual food fair at Tilley Pond Park, which aims to raise funds for Darien's emergency medical services. The fair usually features a variety of food stalls, a silent auction, family games, ambulance tours, and displays of local artists' works.