may-2026
Cinco de Mayo in Downtown Orlando 2026: Where to Celebrate
Downtown Orlando has a way of turning a Tuesday into something worth remembering. On May 5, 2026, Cinco de Mayo lands mid-week, which means bar patios will be packed, margarita specials will be flowing on North Orange Avenue, and the Wall Street Plaza area will have the kind of energy usually reserved for weekends. Whether… Read more
Orlando Fringe Festival 2026: “35 Years Weird” Comes to Loch Haven
Orlando Fringe Festival returns May 12–25, 2026, with a theme that suits it perfectly: “35 Years Weird.” For two weeks, Loch Haven Park transforms into a sprawling outdoor arts village hosting more than 1,000 ticketed performances across theater, dance, comedy, and everything that defies easy categorization. If you’ve never been, this is the year to… Read more
Milk Run 5K 2026: Running Through Orlando’s Milk District
Saturday, May 2 starts before most people’s coffee has brewed, with a 5K through one of Orlando’s most beloved neighborhoods. The Milk Run winds through the Milk District, that tree-lined stretch east of downtown where old bungalows share blocks with indie coffee shops and low-key bars. It is a morning race that feels more like… Read more
Memorial Day Weekend in Downtown Orlando 2026
Memorial Day Weekend, Friday May 22 through Monday May 25, 2026, is the unofficial kickoff to summer in Central Florida, and downtown Orlando treats it accordingly. Three nights of signature programming fill the Orange Avenue corridor and Wall Street Plaza, rooftops stay open late, and brunch spots brace for some of the heaviest Sunday traffic… Read more
Spooky Empire May 2026: Orlando’s Horror Convention Returns
Spooky Empire is back in Orlando for Memorial Day weekend, May 29–31, 2026. Three days of horror film celebrity meet-and-greets, autograph signings, a sprawling vendor floor, film screenings, costume contests, and enough pop-culture nostalgia to keep you occupied from the moment the doors open until they shut. Whether you’re a lifelong horror devotee or a… Read more
Things to Do in Downtown Orlando This May 2026
May 2026 gives downtown Orlando one of its fullest calendars of the year. A beloved performing-arts festival returns for its 35th anniversary, a neighborhood race kicks off the month, Memorial Day weekend stretches across four nights, and a horror convention rolls in right before June. Whether you are here for the culture, the holiday, or… Read more