O'Maddy's Bar & Grille opened its rooftop deck in Gulfport the weekend of June 22, completing an expansion the waterfront bar had in motion before Hurricanes Helene and Milton struck the Tampa Bay area in fall 2024. The addition was confirmed via the operator's Instagram, which described the second-story deck as featuring a large bar centerpiece and ample shaded seating overlooking Boca Ciega Bay.
The project predates the storms — the operator's post notes it was originally planned before Helene and Milton caused damage to the landmark — placing the rooftop's construction among the longer-tail recovery projects that Pinellas County waterfront businesses carried through 2025 and into 2026. O'Maddy's has not publicly specified its original target opening date or detailed the scope of storm damage it sustained.
The rooftop's format tracks the bar's ground-floor character: casual, bay-facing, and built around extended stays. Per the operator's Instagram, the same menu carries upstairs, including a staff-recommended grouper sandwich and oversized cheesesticks — both now available with second-story views of the bay. The deck's bar centerpiece suggests the space is designed to operate independently rather than as overflow from the main floor.
Gulfport's compact waterfront has long distinguished itself from the denser commercial corridors in St. Pete, with a local following that treats the strip as a neighborhood fixture. A rooftop addition is one of the few structural moves that meaningfully expands capacity and draws a new visit reason without altering a bar's essential character — which matters for an operator the community already identifies as a landmark.
No additional programming details or further expansion phases have been announced. The rooftop is now in regular operation following its June 22 weekend debut.
