Things to Do in Jacksonville: May 23 - June 1, 2026

Memorial Day weekend kicks off with free jazz echoing through downtown, and honestly that sets the tone for the next ten days. We pulled together everything happening around Jacksonville from Saturday, May 23 through Sunday, June 1. Beaches, big arena shows, farmers markets, a little St. Augustine magic. Here's what's good.

Music you'll actually want to show up for

The Jacksonville Jazz Festival runs May 21 to 24 in downtown Jacksonville, and the best part is it's free. Multiple stages, food everywhere, that easy holiday-weekend energy. If you only do one thing this weekend, make it this. Details and lineup here.

Want something louder? Shinedown brings the "Dance, Kid, Dance Act II" tour to VyStar Veterans Memorial Arena on Tuesday, May 26 at 7 p.m. It's a big production, so grab tickets before they move. Find tickets.

Same night, totally different vibe: the Happy Together Tour with The Association lands at the Florida Theatre at 7 p.m. Think classic harmonies and a room full of people who know every word. More on Jacksonville concerts.

And the closer is a heavy hitter. The Queens: 4 Legends, 1 Stage puts Chaka Khan, Patti LaBelle, Gladys Knight, and Stephanie Mills on the same bill at VyStar Arena on Sunday, May 31. That's a lot of legend for one night! Tickets and time here.

Beach days and markets

The Beaches Green Market sets up at Penman Park on Saturday, May 23 from 10 a.m. to 2 p.m. Local produce, makers, the usual reasons to wander around with an iced coffee. Check the beaches calendar.

Midweek, the Jax Beach Farmers Market takes over Latham Plaza and the Seawalk Pavilion on Tuesday, May 26 from 3 to 7 p.m. Right next door, the Jax Beach Classic Car Cruise rolls in from 4 to 7 p.m. Chrome, sunset, and the ocean a block away. Pretty hard to beat. Beach event info.

Family stuff and good causes

If you've got kids who need to burn energy, Splash Wars hits the Jacksonville Equestrian Center on Saturday, May 23 from 11 a.m. to 6 p.m. Water battles, slip-n-slides, foam parties, the whole soaked-and-happy situation. Event details.

Feeling like doing some good? The Hope Starts Here 5K steps off at 8 a.m. on May 23 at Operation New Hope. It's an early start, but you'll be done before the heat shows up. Register and learn more.

The following Saturday, May 30, the Edgewater Hometeam Walk-a-Thon runs from 9:30 a.m. to noon at the Beaches Visitor Center. Easy morning, friendly crowd, good cause. More info here.

Worth the short drive

St. Augustine is barely an hour south and it's putting on a show. On Sunday, May 31 from 10 a.m. to 5 p.m. there's an annual festival blending live music with a real reverence for nature, set against the oldest city in the country. Makes for a great day trip. See what's on in St. Augustine.

Heading north instead? Amelia Island keeps a steady drumbeat of festivals and waterfront events all spring, so it's an easy pivot if you want quieter sand and a historic downtown. Browse Amelia Island events.

Quick recap

Ten days, a ton of options. Free jazz to start, arena legends to finish, and a whole lot of beach in between. Pick a couple, text a friend, and go. We'll see you out there next week with a fresh round!