The Cinnamon Bear is an old time radio program produced by Transco (Transcription Company of America), based in Hollywood, California. The series was specifically designed to be listened to six days a week between Thanksgiving and Christmas.

It was first broadcast between Friday, November 26 and Saturday December 25, 1937. Some markets like Portland, Oregon jumped the gun, debuting the program on November 25, Thanksgiving Day. In the first season, Portland broadcast the program on two stations, KALE at 6:00pm and KXL at 7:00pm.

When syndication problems arose at Transco, the program was not officially broadcast in 1940, although some stations might have aired previous transcriptions. No program aired in Portland that year. In 1941, Transco programming was sold to Broadcasters Program Syndicate, and The Cinnamon Bear was on the air nationally once again. In the 1950s, syndication was taken over by Lou R. Winston, also based in Hollywood.