Entertainment: Card Shows, Bike Races and More » Urban Milwaukee

You can feel it in the air – there’s an overwhelming gloominess in the city right now thanks to the unfortunate news of the Giannis Antetokounmpo trade. That’s why it’s important to get out there, take your mind off of it and celebrate what we love about Milwaukee summers – the events! Summerfest is on weekend two, and will feature performances by Post Malone, Kim Gordon, The Mountain Goats and more. The Tour of America’s Dairyland will bring bicycle races to various Milwaukee neighborhoods, and Deer District is hosting a weekend-long tailgating party.

June 25-27: Summerfest Weekend Two

The Big Gig has arrived! Summerfest, the world’s largest music festival,  is here and will once again take place over the course of three weekends at the Henry Maier Festival Park. Each weekend will be packed full of live music on both free and ticketed stages, entertainment such as skateboarding and bmx demonstrations, vendors and more. Music highlights for weekend two include Post Malone, Kim Gordon, Petey USA and more. Be sure to catch featured local acts like Vincent Van Great, Fuzzysurf, and Wire & Nail, and don’t forget to check the Summerfest website to find out about admission promotions like Throwback Thursday, where the price of admission is only $5 and most beverages are half off from noon to 6 p.m.

June 25-28: Tour of America’s Dairyland

Professional and amateur cyclists from all over the world will hop from neighborhood to neighborhood to compete against one another for the fastest completion times! These races are also block parties that will feature various entertainment, food and drinks and family-friendly activities. The races will take place in Bay View on Thursday, Shorewood on Friday, on Downer Avenue on Saturday and in Wauwatosa on Sunday. The Tour of America’s Dairyland is free to spectate. For more information, visit the race’s website.

June 25-28: Deer District Tailgate

Nobody tailgates better than Milwaukee, and the Deer District is proving that point this weekend. Starting and Thursday and running through Sunday, Deer District will host various sports-themed viewings, live music, family-friendly activities and more. Check out a showing of The Mighty Ducks on Friday at 7:30 p.m., and shop the Deer District Farmers Market on Sunday. For a full schedule of Deer District Tailgate happenings, visit the Deer District website.

June 26-28: The Wisconsin Card Show

Whether you’re attempting to “catch ‘em all” in Pokemon or collecting your personal MVPs, there’s something for every trading card enthusiast at the Wisconsin Card Show. All weekend long, vendors will set up shop at Fiserv Forum, giving guests the chance to find that rare card they’ve been searching for or to get autographs from dozens of Packers, Brewers and Bucks current and former players. The Milwaukee Card Expo will run from 3 p.m. to 8 p.m. on Friday, from 10 a.m. to 6 p.m. on Saturday and from 10 a.m. to 4 p.m. on Sunday. More details on the event website.

June 28: Pride on Brady

Brady St. will be filled with live music, performers, vendors and more as part of Pride on Brady, an event that aims to bring Milwaukee communities together in celebration of our LGTBQIA+ members. The event will take place between Farwell Ave. and Van Buren St., and guests can watch live drag shows, get their groove on at a dance stage, speak with community organizers and more. Pride on Brady is free to attend and will run from noon to 10 p.m.

June 28: The Gig’s 25 Year Block Party

Riverwest gem The Gig is celebrating its 25th birthday this weekend and is throwing a party to commemorate the milestone. The Grateful-Dead-themed bar is throwing a block party that will feature plenty of food, live music, raffles and more. Music will begin at 1 p.m. and will feature performances by Midnight Hound, Chicken Wire Empire and Grateful Dead cover band Another One. Guests can play yard games and are encouraged to bring their own yard chairs. The Gig 25 Year Block Party will run from noon to 10 p.m.