May in Tampa Bay is where sunshine meets celebration. As the days get longer and the weather hits that sweet spot, the city comes alive with outdoor festivals, waterfront fun, live music, and experiences that invite you to slow down—or turn it all the way up. From neighborhood happenings to major events, May is the perfect time to get outside, try something new, and soak in everything that makes Tampa Bay shine.
Local market in the heart of Seminole Heights District, held every 3rd Thursday at Common Dialect brewery, with local makers, food trucks, and more. Family and pet-friendly, and free to attend. May 21
Dave Matthews Band is scheduled to perform in Tampa Bay as part of their 2026 North American Summer Tour, bringing their signature blend of rock, jazz, and improvisational jams to the MidFlorida Credit Union Amphitheatre. Known for their electric live performances and loyal fan base, the show promises an unforgettable night of music and summer vibes. Fans can expect a setlist packed with classics, crowd favorites, and a few surprises—making it a can’t-miss concert experience. May 26
Based on the best-selling novel that inspired the iconic film, The Notebook tells the story of Allie and Noah, both from different worlds, who share a lifetime of love despite the forces that threaten to pull them apart. “Full of butterfly-inducing highs and beautiful songs” (Entertainment Weekly), The Notebook is a deeply moving portrait of the enduring power of love. Chris Jones of The Chicago Tribune says The Notebook is “absolutely gorgeous, not to be missed,” and The New York Daily News calls it “a love story for the ages.” May 26-31
ROCK THE COSMOS: MICHAEL JACKSON
Laser Light Shows are taking over the Holloway Digital Dome Theatre, home to the Saunders Planetarium. Step inside America’s second-largest planetarium and experience vivid laser visuals, dynamic music, and dazzling special effects. Designed for all ages, MOSI’s Laser Light Shows have something for everyone. The performance pairs stunning visuals with your favorite Michael Jackson soundtracks. Inside the theater, you won’t just watch the show, you’ll feel like part of it. May 29