Chester Gaylord (February 24, 1899 – July 1, 1984) was a vocalist and among the most active of recording artists in the United States during the late 1920s through the early 1930s.

[1] He began his career as a singer and announcer for radio station WTAG in Worcester, Massachusetts in the early 1920s.

Chester Gaylord's first recordings (in 1920) were saxophone solos for Thomas Edison, whom he had met.

After the Warner Brothers bought out the Brunswick Record company in April 1930 a reorganization occurred and Chester Gaylord's contact was one of numerous artists whose contract was not renewed.

He regularly played 1920s and 1930s songs on piano at The Old Timer, an Irish Pub in neighboring Clinton, Massachusetts.