Recreation is important to residents of Middletown. In addition to the many parks located in the area, the Middletown Nature Center has a nature trail winding through woods and past a stream. A pavilion provides a lovely location for picnics or small events. The Boys and Girls Club offers activities and classes for children, as does the YMCA. There are also more than 20 local golf courses. Bear Creek Golf Club, rated one of the top 40 courses in the U.S. is located in Middletown.
The Premiere Centre for the Arts in Middletown offers classes in dance and music for all ages. Area annual events include live music throughout the summer at the Middletown-Odessa-Townsend Senior Center bandstand, a Fourth of July celebration at Silver Lake Park, the Olde Tyme Peach Festival in August, home and walking tours in the historic districts of each town, and the MOT Big Ball Marathon. Parades include the Hummers Parade (a fun-filled spoof on the Mummers Parade in Philadelphia), the Little League Parade, the Peach Festival Parade and the Christmas Parade.
Middletown was originally a tavern stop about half way between Appoquinimink Creek and Bohemia Landing on the eastern branch of the Bohemia River. This location gave the town its name. The memorial in Cochran's Square (also called Four Corners) was originally built to honor those who died in World War I. Today the memorial is dedicated to all war heroes.