We had a BLAST at the first ever Clark Street Live Street Festival to kick off the fall!
Endless trivia goers from the past and future answered questions to win a wheel spin and went home with a ton of fun free swag – we basically ran out!! No city does a street fest better than Chicago.
What a great way to spend a sunny fall weekend!
Swipe to the end of the carousel to see a very cute guest host ask a trivia question. 🥹😭
See you next year!
We’re heading to Clark Street Live, Wrigleyville’s brand-new street festival, on September 26–27, 2026!
We’ll have a Whaddayaknow? tent set up along Clark Street where you can stop by, spin our trivia wheel, answer questions, and win some prizes. Whether you’re a longtime trivia fan or just looking for something fun to do between sets, come say hi!
Whaddayaknow? Loves Wrigleyville
We’re excited to get to spend some more weekend time in Wrigleyville for this fall festival!
Our regulars will know that we have a whole slew of trivia locations to choose from in the area, from Billy Goat Tavern and The Rabbit Hole to Graystone Tavern, Cheba Hut, and Level Sporting Club. Oh, that’s not all of them! We also work with Stolen Saddle, Kincade’s, Cheesie’s Lakeview, and Tin Roof all nearby.
As a matter of fact, you can head over to Smoke Daddy BBQ for bingo and Merkle’s Bar and Grill for trivia on Friday to kick off a weekend of Wrigley festivities, with the street festival running Saturday and Sunday.
Whether you’re singing along to your favorites, just enjoying this fall weather we are suddenly having, or taking the opportunity to have a few drinks with friends, we hope to see you there!
What To Expect at Clark Street Live
Clark Street Live will feature two stages with live music, local food stands, neighborhood bar participation, and more throughout Wrigleyville, making it a perfect way to spend the weekend.
The Newport stage will be dedicated to country music and the Addison stage will have a range of EDM, reggae, blues, and rock. The festival caters to all kinds of music lovers and is open to all ages, but some areas serving alcohol are still limited to the 21+ crowd.
The country music lineup includes Matt Stillwell, South City Revival, and Good Country. At Addison stage you’ll find Iris Blue, The Gingers, and Radio Gaga, among others.
Where: Clark Street, Addison to Newport, Chicago
When: Saturday, September 26, 11 am – 10 pm & Sunday, September 27, 11 am – 9 pm
FAQ
Does the festival cost money?
Admission is completely free, with a suggested donation to support the festival.
How should I get to Clark Street Live?
Public transit, biking, or walking to the festival is encouraged. The festival may be accessible, but city parking can’t quite say the same…
Will there be food?
Of course! Wrigleyville is pulling out plenty of local vendors, along with neighborhood bars and restaurants along the festival, to make sure that you get all the bites and beverages you could want.
This will be the inauguration of a fun fall festival that you do not want to miss!
Come find the Whaddayaknow? crew and say hi to your favorite hosts, test your trivia knowledge, and maybe walk away with a prize!
We’ll see you there!
Anna Shoultz serves as the Content and Editorial Coordinator for Whaddayaknow? Free Pub Trivia. Her first experience with Whaddayaknow? preceded her move to Chicago by nearly a year, when friends she was visiting took her to trivia at The Green Lady. After officially moving from San Diego, that one-off trivia night became a Chicago staple. Throughout the years, she’s joined friends that are Wednesday regulars at Friar Tuck, popped into seasonal music bingo at Hubbard Inn, and attended various other trivia nights across the city. After all, anyone who knows Chicago in the winter knows that this is one of the best (sometimes only) activities to keep warm, see friends, and get out of the house on gloomy weeknights.
In her role, Anna develops editorial content, visual storytelling, and social media features that introduce new audiences to Whaddayaknow? while celebrating the regulars who make each venue unique. Whether she's highlighting a championship team, spotlighting a neighborhood host, writing about a recent volunteer event, or capturing the energy of a packed trivia night, she enjoys documenting the moments that keep players coming back week after week.
When she's not behind the camera or planning content, you’ll find Anna trying new restaurants across the city, reading at the Lakefront, browsing pop-ups and farmers markets, or, of course, finding her new favorite spot to play trivia!