Choose the history you can still see. Tradewinds carries the longest bar story here. The Milltop and Ice Plant keep the original building work in the room, while O.C. White's puts the evening inside a moved bayfront house from about 1790.
| Bar | Documented history | Choose it for |
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| Tradewinds | Open since 1945 and owned by the Leonard family since 1961 | A longtime tropical lounge with live bands |
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| Ann O'Malley's | Open since 1992 inside an 1878 family home | An Irish pub by the Old City Gate |
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| Milltop Tavern | An 1880s gristmill that became a bar in the 1950s | Daily music above St. George Street |
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| Ice Plant Bar | A 1927 ice plant with the original crane over the bar | House cocktails and a full kitchen |
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| O.C. White's | A house built about 1790 and moved to the bayfront in 1961 | A courtyard, sunset view, and evening music |
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| Stogies | Locally owned for more than 23 years | A listening room with daily music and a fire pit |
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Match the building to the kind of night
Choose Tradewinds or the Milltop when live music is the reason to go. Pick Ice Plant when the cocktail program matters as much as the building. Use O.C. White's for a meal and a bay view. Ann O'Malley's and Stogies work when a pub or listening room fits better than a full dinner.
History and venue details were last verified September 18, 2026. Check the current calendar and age rules before going.