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This Week in Tampa Bay: St. Pete Pride, Ye at The Ray, and Hilary Duff (June 23–29)

May 31, 2026
This Week in Tampa Bay: St. Pete Pride, Ye at The Ray, and Hilary Duff (June 23–29)

This Week in Tampa Bay: St. Pete Pride, Ye at The Ray, and Hilary Duff (June 23–29)

Late June is stacking up. St. Pete Pride Parade returns Saturday with 350,000+ expected in downtown St. Pete, Ye hits Raymond James Friday night, and Hilary Duff opens the week at MIDFLORIDA. Here's what's worth your time.

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Hilary Duff with La Roux — Tuesday, June 23

MIDFLORIDA Credit Union Amphitheatre | 7:00 PM

Hilary Duff kicks off the week with a nostalgia-heavy outdoor show at the amphitheatre. La Roux is opening — yes, the "Bulletproof" La Roux — which makes this more interesting than it might sound on paper. If you grew up in the 2000s, this one's hard to skip.

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Florida's Funniest Comedian Contest: West Coast Semi-Finals — Wednesday, June 24

Funny Bone Comedy Club, Tampa | 7:00 PM

Local comedians compete for the title of Florida's Funniest — the regional semi-finals for the national competition. These shows are always worth it. You're watching people who are genuinely trying to win something, which tends to make the sets sharper than your average open mic night. Cover charge, full bar.

Jessi Uribe — Wednesday, June 24

Seminole Hard Rock Tampa Event Center | 8:00 PM

Colombian singer Jessi Uribe brings his mix of vallenato, cumbia, and regional Mexican sounds to Hard Rock Tampa. One of the biggest names in Latin regional music right now. If you follow the genre, this is the show of the week.

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Ye at Raymond James Stadium — Friday, June 26

Raymond James Stadium | 8:00 PM

Kanye West — performing as Ye — plays Raymond James on a Friday night. The "YE Live" tour announcement came late May, and the show reportedly included a limited batch of free tickets given to fans who registered ahead of time. Raymond James Stadium holds 65,000+, so expect this to be a massive production.

Whatever you think of Ye personally, he doesn't do small. If you're going, plan for parking well in advance — this is a stadium show on the same weekend as St. Pete Pride, so the whole region is going to be busy.

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St. Pete Pride Parade & Festival — Saturday, June 27

Downtown St. Petersburg | North Straub Park | 2:00 PM–9:00 PM

This is the anchor event of the week. St. Pete Pride is one of the biggest Pride celebrations in the Southeast — around 100,000 marchers in the parade, 350,000+ visitors across the whole weekend. The festival runs at North Straub Park with live performances, vendors, and the parade route through downtown.

Free parking is available at St. Petersburg High School (2501 5th Ave North) from 11 AM to midnight, with PSTA bus service. Downtown will be packed — if you're heading over from Pinellas Park, New Port Richey, or the north end of the county, go early or take the bus.

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Godfrey at Funny Bone — Friday–Sunday, June 26–28

Funny Bone Comedy Club, Tampa | Multiple shows

Stand-up comedian Godfrey — known for his impressions and social commentary — plays multiple sets across the weekend. Friday has 7:00 PM and 9:45 PM shows. Saturday adds a 6:30 PM. Sunday wraps with a 6:30 PM closer. Reserve ahead; Funny Bone shows sell out on weekends.

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The Short Version

Best for families: St. Pete Pride daytime activities and the parade route in downtown St. Pete. Best for music: Ye at Raymond James Friday, Hilary Duff at MIDFLORIDA Tuesday, Jessi Uribe at Hard Rock Wednesday. Best for a cheap night out: Florida's Funniest Comedian Contest Wednesday at Funny Bone, or Joe Machi's comedy run at Side Splitters Thursday through Sunday.

Whatever you do, book parking and rideshares early if you're headed downtown Saturday — two big events within 20 miles of each other means traffic will be ugly by midday.

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