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Published on April 30, 2026
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Things To Do: Weekend Of May 1, 2026

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Bright, vibrant event flyer with the title 'THINGS TO DO FOR THE WEEKEND' over a sunny, bustling street festival. Features people smiling and enjoying food at a market with colorful tents in a downtown city setting.

Dunedin, FL

Day, DateTimeWHOWhereAddress
Fri, May 19:00 AM – 2:00 PMDunedin Downtown MarketPioneer Park420 Main St
Fri, May 111:00 AM – 4:00 PMChamber Golf TournamentDunedin Golf Club1050 Palm Blvd
Fri, May 12:30 PM – 5:30 PMJupiter Hammerheads vs. Blue JaysTD Ballpark373 Douglas Ave
Fri, May 16:00 PM – 8:00 PMMother-Son Game NightOur Lady of Lourdes School730 San Salvador Dr
Fri, May 17:00 PM – 9:00 PMSunset Music Series: Wendy BarmoreWeaver Park1258 Bayshore Blvd
Fri, May 17:00 PM – 10:00 PMCarl August (Live Music)Woodwright Brewing Co.985 Douglas Ave
Fri, May 18:00 PM – 11:00 PM90s Total Requests w/ Live BandDunedin Brewery937 Douglas Ave
Sat, May 28:00 AM – 11:00 AMHog Hustle 5K Run/WalkHale Senior Activity Center330 Douglas Ave
Sat, May 29:00 AM – 11:00 AMDunedin Beach CleanupCurlew Landings61 Causeway Blvd
Sat, May 29:00 AM – 2:00 PMDunedin Downtown MarketPioneer Park420 Main St
Sat, May 22:00 PM – 5:00 PMFirst Day of Camp WoodwrightWoodwright Brewing Co.985 Douglas Ave
Sat, May 27:00 PM – 10:00 PMDJ 45RevolverDunedin Brewery937 Douglas Ave
Sat, May 28:00 PM – 11:00 PMRushour – Rush TributeBlur Nightclub325 Main St
Sun, May 311:30 AM – 1:30 PMBacon & Beer BrunchCaledonia Brewing587 Main St
Sun, May 32:00 PM – 5:00 PMPamela Jo (Live Music)Woodwright Brewing Co.985 Douglas Ave
Sun, May 33:00 PM – 8:00 PMCharity BazaarReboot Arcade Bar420 Patricia Ave

Palm Harbor, FL

Day, DateTimeWHOWhereAddress
Fri, May 17:00 PM – 9:00 PMSlightly StiltedStilt House Brewery625 Alt 19
Fri, May 17:00 PM – 10:00 PMTrey Wanvig & Detroit MikeFairway Pizza & Sports Pub2901 Alt 19
Fri, May 18:30 PM – 11:30 PMGlory Hogs Band (Rock)Snappers Grill & Comedy Club36657 US Hwy 19 N
Sat, May 22:00 PM – 10:00 PM2nd Annual Hero FestDowntown Palm HarborFlorida Ave & 11th St
Sat, May 22:00 PM – 10:00 PMRock The Harbor (Live Music)Crabby Bill’s Palm Harbor1114 Florida Ave
Sat, May 22:30 PM – 4:30 PMGreg WestStilt House Brewery625 Alt 19
Sat, May 26:30 PM – 9:30 PMCrossfire Creek (Country)Downtown Main StageDowntown Palm Harbor
Sat, May 27:00 PM – 10:00 PMLive Local MusicRumfire917 11th St
Sat, May 29:00 PM – 11:00 PMKaraoke NightStilt House Brewery625 Alt 19

Ozona, FL

Day, DateTimeWHOWhereAddress
Fri, May 15:00 PM – 9:00 PMFrank Dancey (Acoustic)Marker 81420 Bayshore Blvd
Fri, May 16:00 PM – 9:00 PMLive Local MusicThe Ozona Pig311 Orange St
Sat, May 22:30 PM – 5:30 PMRockin’ RobOzona Brewing Company315 Orange St
Sat, May 25:00 PM – 9:00 PMWeekly Live EntertainmentOzona Blue Grill125 Orange St
Sat, May 26:00 PM – 10:00 PMLive Music & Fresh CatchMolly Goodhead’s Raw Bar400 Orange St
Sat, May 28:00 PM – 11:00 PMAudioStarOzona Brewing Company315 Orange St
Sun, May 31:00 PM – 4:00 PMSunday Blues SessionOzona Brewing Company315 Orange St
Sun, May 34:00 PM – 7:00 PMMike CeeOzona Blue125 Orange St

Tarpon Springs, FL

Day, DateTimeWHOWhereAddress
Fri, May 15:00 PM – 9:00 PMThe Jazz PhoolsH’ours Creole Smokehouse310 E Tarpon Ave
Fri, May 16:00 PM – 10:00 PMFirst Friday: Art, Music & VendorsHistoric DowntownW Tarpon Ave
Fri, May 17:00 PM – 10:00 PMLive Local EntertainmentSponge Docks DistrictDodecanese Blvd
Sat, May 210:00 AM – 5:00 PMSponge Docks Sightseeing & ShoppingSponge Docks750 Dodecanese Blvd
Sat, May 28:00 PM – 11:00 PMLive Music at the DocksAnclote Brew735 Dodecanese Blvd
Sun, May 312:00 PM – 4:00 PMTraditional Greek MusicSponge Docks RestaurantsDodecanese Blvd
Sun, May 31:00 PM – 4:00 PMAcoustic Sunday SessionTarpon Springs Distillery605 N Pinellas Ave

Clearwater, FL

Day, DateTimeWHOWhereAddress
Fri, May 16:00 PM – 9:00 PMIzzy Bradburn (Acoustic)Salty Crab Bar & Grill462 Mandalay Ave
Fri, May 18:00 PM – 11:00 PMRich Sheldon Band3 Daughters Brewing381 Mandalay Ave (3rd Fl)
Fri, May 18:30 PM – 10:30 PMHeadliner Comedy SeriesClearwater Comedy Club483 Mandalay Ave
Sat, May 24:00 PM – 7:00 PMJustin Alderman DuoHogg Daddy’s Beach Bar752 S Gulfview Blvd
Sat, May 26:30 PM – 8:30 PMSunsets at Pier 60Pier 60 Park1 Causeway Blvd
Sun, May 312:00 PM – 4:00 PMLive Beachfront MusicFrenchy’s Rockaway Grill7 Rockaway St
Sun, May 32:00 PM – 10:00 PM3rd Annual Cinco de Mayo Taco FestCoachman Park300 Cleveland St

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Dunedin resident since 1998. I am the person behind the camera and the words. I have watched this town change—some for the better, some still figuring out. What has not changed is my connection to it. The beaches. The small blocks downtown and uptown where Honeymoon Island area is located. The way the light hits the water in the evening. The people who stay, and the ones who keep coming back.

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