Main Street Winter Haven will host its 18th Annual Oktoberfest on Friday, October 10, 2025, starting at 6:00 PM in Central Park. The event features a free admission option to enjoy food and live music by the Brassheart Band, while a ticket is required to sample a wide selection of German, American, and craft beers and wines. Attendees can also participate in a free Stein Hoisting Contest.