#1 33rd Annual King of the Beach
Experience one of Pinellas County’s most iconic waterfront celebrations at the King of the Beach Festival & Tournament, taking over Madeira Beach for a full weekend of fishing, food, music, and family fun this weekend. This can’t-miss event blends the legendary kingfish tournament with a lively festival atmosphere—featuring local food vendors, nightly live music, carnival-style games, and a Friday night Founders Day celebration with fireworks. Kids can get in on the action with a seawall fishing tournament, prizes, and even free rod-and-reel giveaways for early sign-ups. Whether you’re casting a line or just soaking in the coastal energy, this is everything you love about Madeira Beach in one unforgettable weekend.
Learn more in our April Cover Story at https://www.paradisenewsfl.com/33rd-spring-king-of-the-beach/.
#2 Derby Day at The Pier
Dress to impress and celebrate in style at Derby Day at the Pier this Saturday, May 2nd 3–9pm at Spa Beach Park. This 21+ Kentucky Derby watch party brings big hats, bow ties, and waterfront vibes together for an unforgettable afternoon benefiting local nonprofits. Enjoy high-energy festivities, a best-dressed crowd, & the thrill of the “fastest two minutes in sports” in one of St. Pete’s most scenic settings—rain or shine, they’ll party on.
Learn more at https://stpetepier.org/event/derby-on-the-pier/.
#3 Pinellas Pepper Fest
Turn up the heat at the 19th Annual Pinellas Pepper Fest, happening Saturday & Sunday, May 2-3 10am–5pm at England Brothers Park. This free, family- and pet-friendly festival is packed with bold flavors—featuring everything from spicy sauces and salsas to wild food challenges like pepper eating contests & the infamous Lolli Lick-A-Thon—plus live music and tons of vendors bringing the heat all weekend.
Learn more at https://www.facebook.com/events/1143173454363079/
#4 Sunscreen Film Festival
Lights, camera, St. Pete! The Sunscreen Film Festival returns April 30–May 3, bringing a dynamic mix of independent films, documentaries, shorts, anime, and international features to downtown at AMC Sundial 12 and Green Light Cinema & Lounge. With tickets starting at $15 (and multi-day passes available), this immersive event also offers workshops, guest speakers, and the chance to connect with filmmakers and creatives.
Get tickets at https://sunscreenfilmfestival.com/.
#5 Tampa Bay Chalk Fest
Watch the streets come alive with color at the Tampa Bay Chalk Festival this Saturday, May 2nd 10am–4pm along 22nd Street South Arts District. This free, family-friendly event features 25+ artists transforming the pavement into stunning works of art inspired by the theme “Our Watery Futures 2026,” with opportunities for kids, families, and creatives of all ages to grab some chalk and join in the fun.
Learn more at https://tampabaychalkfestival.com/.