The Watertown Players was founded by Bill Jannke in 1988 as a group to perform his annual holiday plays at the Octagon House Museum . This is still a large part of the group's yearly out-put.

At that time there were no other local groups actively presenting theatrical productions in Watertown, with the exception of the local high school and colleges. In the early days of the Players there were only the yearly plays. In 1991 the group made their first attempt at a non-holiday production when they presented an original adaptation of Mark Twain stories for cable television. After that it was back to the yearly shows.

Then in 1998, Brandon Thomsen, a member of the company since childhood, asked permission to use the name to produce "The Secret Garden". From this beginning, the Watertown Players began to break away from once a year productions to form a yearly season.