Hey there, Clearwater! It’s May 22, 2026, and if you’re looking for something to do this weekend, you’re in luck! With Memorial Day Weekend just around the corner, Clearwater is buzzing with excitement and a whole lineup of events that you won’t want to miss. Let’s dive right in!
First up, on May 23, you can catch the LoveLoaf Live performance at Hogg Daddys Beach Bar. This popular spot, located at 752 South Gulfview Boulevard, Clearwater, Florida 33767, is perfect for soaking up the sun while enjoying some incredible live music. If you’re hungry, don’t forget to try their renowned Bone-in Wings—they’re hot, well-seasoned, and perfect for sharing. And let’s not overlook the Grouper Sandwich, featuring a thick slice of grouper on a toasted bun with crispy toppings and a zesty citrus note. It’s a Florida classic!
On the same day, the Hyatt Regency Clearwater Beach Resort and Suites will host its Night Market under the SHOR x The Market Culture theme. It’s going to be a vibrant atmosphere with great food, drink, and local vendors. You might also want to check out the Memorial Day Weekend events happening at Shephard’s Beach Resort, where the fun just keeps rolling.
Live Music Galore!
Music lovers are in for a treat! On May 23, the Jorge Valentine Band will perform at Shephard’s Beach Resort, providing a perfect soundtrack to your beach day. If that’s not enough, swing by the MUSIC4LIFE venue on the same day to catch Ari Hest—it’s sure to be a night of unforgettable tunes!
And for those looking to unwind with a glass of wine, the Club Wine-O Social & Wine Tasting at Aspirations Winery is a must-visit. Sip on some exquisite wines and enjoy the lovely Clearwater vibes. Then, on May 24, don’t miss the FLO-RAW Live performance at Shephard’s Beach Resort, which promises to be an electrifying show!
Food and Fun at Hogg Daddys
If you’re planning to eat out, Hogg Daddys Beach Bar is not just about music; it’s a beloved hangout for both locals and tourists. The atmosphere is laid-back, making it an ideal spot for a quick lunch or leisurely dinner. Plus, with a full bar and plenty of TVs for sports, you can kick back and enjoy the game while munching on some Pretzel Bites or their Seafood Bar Junk—a mixed appetizer that’s perfect for sharing.
On May 24, you can celebrate Hogg Daddys’ 2nd Anniversary with Chas Collins, right after you take a trip to the Tinis and Weenies event at Sandcastle Arcade Bar & Grill. And if that’s not enough excitement for you, check out the Banjoe Steve NoBS Band at Hurricane Eddie’s. It’s a weekend full of music, food, and fun!
For a complete list of events happening this weekend, check out the full details at All Events in Clearwater. So grab your friends, soak up some sun, and enjoy all that Clearwater has to offer this Memorial Day Weekend!