Wine & Whiskers is Heartland Humane Society's premier fundraising event. This event, a gala silent and live auction with plated dinner and wine/beer/cider, is in its 16th year. The event has a theme every year and guests are encouraged to dress in theme-appropriate costumes and can compete to win prizes. This will be Wine & Whiskers' 15th year, the last 5 of which have sold out. This year the event is titled “Wine & Whiskers 2019 – A Tail of Mutts & Magick” and will have a medieval fantasy theme.

Funds raised at Wine & Whiskers support the animals and programs at Heartland Humane Society. Heartland cares for 1,500 animals each year and serves the community with programs including animal adoptions, lost & found services, humane education, a pet food bank, vaccination and spay/neuter clinics, and the Safe Housing Program, which provides confidential housing for animal companions of families in crisis.