In 1986, the City of Kitchener hosted the first Ontario Senior Games called Actifest. These successful Games established the framework for future Ontario Senior Games. District games would be held annually, and Actifest would be held during August in even-numbered years.

In 1999, the International Year of Older Persons, the announcement of the first-ever Winter Games for seniors was made. And in March 2000, Collingwood hosted these Games. District OSGA winners in sanctioned events qualify to compete in Actifest and Winterfest.