Middletown was initially just a stop for traders about halfway along a cart road between the Appoquinimink Creek in Delaware and the Bohemia River in Maryland. A farming community rose among its rich soil in the 1600s, and settlers began to call the area home. The town was incorporated in 1861, and its limits stretched one-half mile in each direction from the crossroads at Main and Broad Streets. Middletown developed its own industry of trade and agriculture and became locally famous for crops such as peaches. The number of Middletown residents increased slowly until the town's vast stretches of farmland and proximity to four major cities began to attract residential and commercial developers in the 1980s. The population skyrocketed from 2, 946 in 1981 to 18, 995 in 2011, and the boundaries were extended multiple times. The community's charm and agricultural roots still remain, and thousands flock to the town annually to celebrate its heritage at the Middletown Historical Society's Olde-Tyme Peach Festival.