Historical records show that organized baseball has been played in Rutland, Mass., since at least 1903. In May 1952 the first Board of Directors for the Rutland Boys Baseball League were elected, and the league was incorporated with the state of Massachusetts as an official nonprofit organization in 1971. In 1989 the Rutland Boys Baseball League was restructured into Rutland Little League Baseball, Inc., and was chartered with Little League Baseball, Inc. of Williamsport, Penn. (Read more about our history by clicking on “History of Rutland Baseball” on the menu to the left.) In recent years, the league has lent its support to Rutland's softball program for girls.

Today, more than 400 boys and girls participate in Rutland Baseball and Softball. For the 2018 season, the league sponsored ten Tee Ball teams (instructional level ages 4-6), six AA teams (coach-pitch teams for ages 6-8), six AAA teams (Little League minors level, ages 9-10), five LL teams (Little League majors level, ages 11-12), three Babe Ruth teams (ages 13-15), and one Big League team.