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Start a Top 5 for Holiday BarsEditor’s picks
Press picks, until locals rank their own Top 5s. Sourced from the local food press. As seen in Urban Milwaukee, OnMilwaukee, and Milwaukee Magazine. Updated September 2026.
Pufferfish · Downtown
Each winter, the rooftop and indoor bars at this downtown tiki lounge lean into a tropical Christmas theme as one of a small number of officially licensed Sippin' Santa locations nationally. Space heaters and a fireplace keep the rooftop deck usable through the cold months while both indoor rooms open up for the transformed program. The regular tiki drinks give way to a dedicated holiday cocktail list and limited-edition glassware for the season. The usual tropical bar returns once the new year begins.
At Random · Bay View
Each winter, this Bay View cocktail lounge's back patio turns into an outdoor holiday village, with a run of small heated huts strung with lights for guests to duck into out of the cold. A rotating list of seasonal cocktails, hot drinks and ice cream-based drinks keeps the huts warm, and the space stays open to all ages during the day before switching to a 21-and-over crowd in the evening. The indoor cocktail lounge keeps running behind it, with the patio reverting to its usual look once the season ends.
The Tin Widow · Walker's Point
Each winter, this Walker's Point cocktail bar goes all in on Christmas as one of the country's Miracle pop-up locations, filling the room with tens of thousands of string lights and wall-to-wall holiday decor. The regular bar gives way to a dedicated menu of holiday cocktails for the season, plus a kid-friendly cocoa bar on weekend afternoons in December. The transformation runs from late November well into the new year, drawing a packed, festive crowd before the space reverts to its usual look.