Sumter Senior Services has two major fundraising events during the year. The first, which is collectively called Sumter WineFest, offers wine tasting and fine dining. Included events are Sumter Sip and Stroll, Tapas and Wine, Sumter WineFest and Evening with Loosh. To learn more about this event, visit the Sumter WineFest website.

The second event is the Backyard Jamboree. This includes wine tasting, outdoor grilling and famous local BBQ, accompanied during the last two events by foot-stomping Blue Grass music provided by Wild Rain. Check out the Backyard Jamboree website.