Acquired in 1929, with the persistence of then mayor Cecil E. Jackson, Windsor City Council voted in favour of purchasing the land from the Jockey Club.

The original World War II monument was an Avro Lancaster bomber aircraft FM212; it was removed in 2005 due to the effect that over four decades of exposure to the elements was having on it, and replaced by more weather-resistant fibreglass models of a Hawker Hurricane and a Supermarine Spitfire fighter.

In 1991, both the lighted tennis courts and the lawn bowling greens were upgraded and repairs made to the cedar pergola structure.

Many of the walkways are in well-lit and open areas, but there are a few that lead to shade, or to quiet spots tucked away between bushes and tall plants.

In 2015 the Greater Essex County District School Board had re-assumed the property and entered a land use contract with the AKO Fratmen.

The new Bandshell was used for many events throughout the 60's and 70's including the Emancipation Day festival and Windsor's Battle of the Bands.

[3] Emancipation Day celebrations in Jackson Park first began as smaller festivities hosted by Windsor citizens, some who are descendants of enslaved African-Americans who searched for freedom through the Underground Railroad.

[4][5] The celebration attracted hundreds of thousands across North America including renowned musicians like Diana Ross, Stevie Wonder and The Temptations; as well as notable civil rights activists such as Martin Luther King, Rosa Parks, Adam Clayton Powell and Eleanor Roosevelt.