When classes are in session, OLLI provides regular single event educational programs that are free and open to the greater community. Weekly OLLI Ashland Community Lectures are held monthly on a Wednesday from 1:00 pm to 3:00 pm. In addition, monthly OLLI Medford Community Lectures are held the second Friday of the month from 1:00 to 3:00 pm. A special Vital Issues Forum is typically scheduled once a year.
OLLI has also established collaborative partnerships with Ashland at Home, Choosing Options, Honoring Options (COHO) and ScienceWorks Hands-On Museum.
OLLI further extends its community outreach through its OLLI Ambassador Program. This program provides a two-way conduit of information between OLLI and community organizations with missions that overlap with that of OLLI.