Arts & Entertainment
Downtown Milwaukee’s Jack-O-Lantern Jubilee Returns to Baird Community Commons on Saturday, Oct. 24
Get tangled up in Halloween fun with free pumpkins, entertainment, and an expanded backdrop of seasonal lights
Oct 20th, 2026 by Milwaukee Downtown, BID 21THE BOYS FROM BARABOO a Wisconsin-set, Music-filled Play About the Ringling Brothers
Local playwright Heidi Armbruster chronicles the rise and fall of Wisconsin’s famous circus family
Oct 20th, 2026 by Next Act TheatreWorld Series Block Party Takes Over Historic Third Ward Friday & Saturday
Two days of Brewers baseball, live sports programming, food, cocktails, FOX One’s Relive Live and more will bring the World Series to Catalano Square and the Third Ward Beer Garden
Oct 20th, 2026 by Historic Third Ward AssociationMilwaukee Theater District and Milwaukee County Historical Society Announce “Behind the Marquee” Exhibit
Opening Jan. 21, 2027, the exhibit celebrates Milwaukee's theater legacy through historic artifacts, theatrical treasures and special programming.
Oct 20th, 2026 by Milwaukee Theater DistrictKegel’s Inn Hosts Free Brewers World Series Big Screen Watch Parties in Its Historic Beer Garden, One Mile from American Family Field
Every game on a giant outdoor screen, no ticket needed, with a new Ballpark Menu, German favorites and cold beer as Milwaukee celebrates its first World Series in 44 years.
Oct 18th, 2026 by Kegel's InnCanadian Pacific Holiday Train Returns to Wauwatosa Village on December 9
Train stop will benefit Tosa Cares Food Pantry; aims to raise awareness of local food insecurity
Oct 15th, 2026 by Village of Wauwatosa Business Improvement DistrictFirst Stage Celebrates 40th Season With Dr. Seuss’s How the Grinch Stole Christmas!
Led by Jake Horstmeier as the Grinch, local artists and young performers bring First Stage’s signature heart to a beloved holiday classic.
Oct 14th, 2026 by First Stage























