1958 - The Kiwanis club of Kewaskum started youth baseball and continued to organize is until 1967. There were only 3 teams, and they played their games at the Kewaskum High School.
1968 - Tom Larsen and Harry Roecker took over the youth baseball in Kewaskum for the next 3 years and turned it into a traveling league.
1971 through 1974 - There was no youth baseball in Kewaskum, because nobody was willing to run the program.
1974 - The population of Kewaskum was 2,330 people
1975 - The Kewaskum Jaycees started youth baseball up again in Kewaskum. They started playing games behind Holy Trinity School and eventually moved games to behind the High School. The Jaycees ran youth baseball until 1982. Kewaskum had 4 hardball teams and 6 co-ed softball teams.
1977 - The Kiwanis Club donated $77,000.00 to the Village to build Kiwanis Park. It wasn't until 1982 when baseball fields were added to the park.
1980 - The population of Kewaskum was 2,319 people.
1982 - Youth baseball was taken over by Jerry Marx and Tom Bartelt. This was also the year when youth baseball moved its games to Kiwanis Park, where the games are currently played. There were only 2 fields at the park for youth baseball. They were both located on the west side of the park. One field was on the south side of the creek and the other was on the north side of the creek. In the late 80's, early 90's, Kewaskum had 1 midget team, 1 little league team and 1 pony team. Along with co-ed youth softball.
1989 - Dean and Coyla Scheel took over the youth program. They organized youth baseball in Kewaskum until 2003. Under Dean and Coyla, youth baseball grew to 3 midget teams, 2 little league teams, and 1 pony team. All of these teams were traveling team's, which belonged to the Kettle Moraine league. Dean was also the President of the Kettle Moraine league. Softball also became a girls league.
1990 - A third field was added to Kiwanis, and men and woman's softball leagues started in Kewaskum. Women played on Monday nights, and men played on Wednesday nights. The population of Kewaskum was 2,514 people.
2000 - The population of Kewaskum had risen to 3,277 people.
2003 - Tom and Denise Kudek volunteered to take over the youth program. The Kudeks ran the youth program from 2003 until 2008. During this time Kewaskum had 14 teeball and rubberball teams, 2 midget teams, 2 little league teams and 1 pony team, along with 6 girls softball teams. In 2008, realizing how big the youth program was becoming, Tom and Denise started the Kewaskum Athletic Association. Tom was the first president of the association and in the associations first year, girls softball was swithed into all fast pitch teams and they became traveling teams. KAA made the switch because the High School program was also fast pitch.
2009 - Randy Schlice was elected as the new KAA President, along with Chad Cook as Vice-President, Jim Murray as Treasurer and Bonnie Herman as Secretary. League representatives, were also elected to oversee all the individual leagues. Kewaskum's youth program began to grow. Also in 2009 the KAA started youth flag football in Kewaskum. The first year there were a total of 12 teams.
2010 - Kewaskum had 20 teeball and rubberball teams, 5 midget teams, 3 little league teams and 3 pony teams. Girls fast pitch grew also, 2 rookie teams, 2 minors teams, and 2 major teams. The population in Kewaskum in 2010 was 4,004 people.
2011 - Over 600 kids were involved in a sport associated with the KAA. There were 18 tee ball/rubberball teams, 11 hardball teams and 7 girls fast pitch teams. Over 150 games took place at Kiwanis Park in the summer of 2011!!