Oldsmar is a particularly fun place to visit during its signature events. The town's Oktoberfest, offering authentic German food, German beer, live entertainment and a Munich-style tent, is known as one of the best in Central Florida, while the three-day Freedom Fest is a family-friendly, Memorial Day street festival. Oldsmar's longest-running festival is Oldsmar Days, featuring a bevy of classic cars, live rock 'n' roll, a carnival and parade. If you love horse racing, check out Tampa Bay Downs, the area's only Thoroughbred horse track, with live racing from December through May.
Bonus fun fact: This town has more parks per square mile than any other city in the state. Soar above the tree tops of Mobbly Bayou Wilderness Preserve on a zip line tour with Empower Adventures Tampa Bay, or paddle a canoe along trails in the bay and enjoy the shore’s undeveloped parkland and natural beauty.