For outdoors enthusiasts, the Hillsboro Parks Department maintains several areas for public enjoyment. Hillsboro City Park was inaugurated in 1984 and is outfitted with pavilions, rest rooms, playground equipment and picnic areas to complement the natural beauty of the spacious acreage. Additionally, R.W. McMullin Park is downtown and perfect for an afternoon stroll on beautifully-maintained grounds. Finally, a children's park is an ever-popular destination for kids. With all the playground equipment children could ever want, the downtown park is a year-round destination of choice from families all around the area.
The Hillsboro Homecoming Festival also is a family-oriented street fair with a parade, live music, art exhibits, games, food and rides. A golf tournament, which takes place at Raintree Country Club, is also part of the festivities.
In July 2005, the Jefferson County Fair and Horse Show will celebrate its 60th year of entertaining visitors from around the Midwest. The Horse Show began in 1945 and eventually grew in popularity to the point at which a fair was added.
The annual Dual Demolition Derby is always a fun family outing and is priced accordingly. The Hillsboro Community Civic Club also hosts a rodeo each September and a Motor Madness monster truck and motorcross show each August. For an experience that adds history lessons to the fun, the Governor Thomas Fletcher Home, which is on the National Register of Historic Places, has been restored to recall its 1851 construction and acts as a museum of Hillsboro and Missouri history. The Schubel House in downtown Hillsboro and Sandy Creek Bridge just north of the city also resonate with 19th-century history.