The town started as a live-in Old West motion picture set, built in the 1940s. A number of Westerns and early television shows were filmed in Pioneertown, including The Cisco Kid. Roy Rogers was one of the original developers, and Gene Autry frequently taped his show at the six-lane bowling alley, opened by Rogers in 1949, and still in operation today. School-age children were hired as pinsetters until the installation of automatic pinsetting equipment in the 1950s. Autry also had his own room at the Pioneertown Motel, today a Western-themed establishment with individually decorated rooms.
Pioneertown's facade has an exceptionally realistic look, right down to actual bullet holes in the signage and functional hitching posts for horses used in filming.
Mock gunfights are staged from April through October along Pioneertown's Mane Street (sic). By contrast, the town as well as the surrounding desert towns are home to a series of experimental art installations.
On July 11, 2006 a wildfire started by lightning raced through Pioneertown. The blaze, named the Sawtooth Complex fire also burned into Yucca Valley and Morongo Valley. Firefighters managed to save the historic movie set buildings, but much of the surrounding desert habitat was damaged. Among the buildings saved was Pappy and Harriet's Pioneertown Palace, a longtime local club and landmark built within one of the original sets and which counts notable musicians among its regular patrons, among them Eric Burdon.