Cheeriest Place in the Cheer District
Milwaukee's holiday season has officially kicked off with the transformation of the Deer District into the Cheer District, complete with a grand Christmas tree lighting and a bustling holiday market.

There’s no official start to the Holiday Season, but as far as we’re concerned, it began when the lights were turned on in the Deer District last night, transforming it into the Cheer District.
Milwaukee’s mayor, Cavalier Johnson, flipped the switch on the city’s Christmas tree as part of the kickoff celebration at the Cheer District Holiday Market. The annual event runs daily until November 30 (with the exception of Thanksgiving) and features food, drinks, local vendors, holiday lights, and photo backdrops for those lucky enough to look like a tired, weather-beaten Drink Wisconsinbly Week in Review writer.
This is the seventh installment of the market, and it’s always very joyous and festive. But one thing they don’t mention in the press releases or on the official website is that there is a 3,000-square-foot area in the southeast part of the Cheer District that has an even greater concentration of holiday magic.
Our own independent investigation confirms that this space has more jubilation, sparkle and general merry-making than anyplace else on the plaza. It’s practically a Hallmark movie in there.
To find this enchanted spot, look for a red circular sign with white lettering in the sky and then follow it, Three Wise Men-style. Next, pass through the doors marked “Drink Wisconsinbly Pub,” and then bask in the seasonal splendor, with a twinkle in your eye, a ruddy glow on your face, and a DW Brandy Hot Toddy in your hand.
You can find more information about the Cheer District on the Deer District website, and about the DW Pub on ours. We look forward to being the backdrop for your core holiday memories as they’re formed.



