1940 - George Rockwood donates the land to the City with his intention to create an area that would be placed under the Parks and Recreation Department and developed for public park and playground use and enjoyment. The 15.78 acres of land had been used previously as pasture and had a value of $3,000.
1942 - Softball diamond and park roadway constructed.
1950 - The City Council approved and ordered that a portion of Rockwood Field, a public playground, be used for school purposes.
1954 - The City Council approved and ordered the section of Rockwood Field, transferred to the School Department in 1950, be transferred back tot he Parks and Recreation Commission.
1955 - Baseball backstop constructed.
1966 - Baseball infield was remodeled and the Little League field was enclosed with fencing.
1995 - 2005 - Worcester Fast Pitch Softball and Jesse Burkett Little League invest labor and materials to improve and upgrade facilities at Rockwood Field.
1942 - Present - Multiple sports programs make use of the facility including Little League Baseball, Babe Ruth Baseball, Adult Baseball, Various Softball Leagues, Youth Soccer Leagues, Football Leagues and College Athletic Programs and Teams.