Why Whaddayaknow? loves Graystone Tavern
You’re walking through a sea of Cubs jerseys worn by 20-somethings who have had 20-something beverages throughout the day. Lines and crowds roar around you. You’re desperate for a respite. You want a place where you can talk to your friends but instead you see nothing but standing-room-only crowds and a constant roar.
South on Sheffield and suddenly, an oasis appears. You walk in.
And enter, Graystone Tavern, just blocks away from the famous Wrigley Field in Chicago. You’ll smell the delicious fare of Chi Hunter. The Graystone sauce on their delicious chicken wings – a unique blend of BBQ and buffalo sauce – is to die for! Let’s not forget their epic smash burger either! Feel the neighborhood vibes as you take a seat at the bar to be immediately greeted by the talented and friendly staff.
The Pre-Game and Game-Day Destination
Where most bars in the area focus on partying after a Cubs win, and are often claustrophobic and raucous, Graystone is different. It’s a neighborhood bar that contains multitudes. One night you see a community space filled with regulars gently teasing the staff and each other. The next, a screening of the Bachelor in the back bar and a bachelorette party in the front. No matter the time, day or night, you’ll find an experiene. Most importantly, you’ll find a community.
For example, they support over half a dozen of teams, and do so full-throatedly. The Cubs, of course, but also Chelsea Football, Columbus Crew, Minnesota Vikings, BVB Chicago’s youth soccer club, The University of Washington, The American Outlaws Chicago Chapter’s youth soccer, and Kansas State athletics.
But maybe most importantly, they also have long been a supporter of Whaddayaknow? Team Trivia.
Origins of Graystone Tavern
Opened in 2015 at 3441 N. Sheffield Ave., they greatly expanded their space with an enclosed patio area that is open year-long. Dozens of TVs show whatever game you want to see (as well as Whaddayknow? Trivia questions). Where they once had a concrete space with a few tables, they now have an enclosure with soft lighting. Their brand new second bar with a warm wooden enclosure ss perfect for college football screenings or tiki nights.
Just a stone’s throw away from Wrigley, it’s a great pre-game spot for Cubs fans, for their Columbus Crew soccer fanbase to see televised Crew games at one of the only bars in town that screens them, and on College Football weekends they go all out with their Washington and Kansas State game coverage.
We’ve helped provide music and encouragement to a Washington and Kansas State football double-header. We can confirm it’s quite the experience to watch a game and hear the fight song after every touchdown for the team everyone there is to support. Graystone isn’t just a bar for its supporters, it’s a bar that excites supporters! When Washington made the playoffs in 2023, you could not BELIEVE the excitement from all the patrons who came out just to root their team on.
Whaddayaknow at Graystone Tavern
But they also know how to do trivia. We host our famous pub event trivia game EVERY Wednesday at 7 p.m. where our players get to take advantage of their great food offerings and drink selection while playing for $50 (for first place), $25 (for second) and a round of shots for third!
The winning team gets a chance to win even more! Graystone holds a Plinko game which, if you win, can result in a CASH PRIZE of anywhere from $100 to $1,000+. If the game isn’t won the prize goes up each week until we have a winner!
Over the years, we’ve gathered a great group of regular teams to battle while soaking in the laughter and reasonably priced drinks at Graystone. The Chel-Kings, Weird Tuesdays, Sleepover! At the Grocery Store (who one week went as “Engaged! At the Grocery Store” – we’ll let you guess the subtext behind that) and so many more have become both foes and friends through our weekly trivia events.
8 Crazy Nights: A Hanukkah Pop-Up Like No Other
Graystone even hosts one of the most unique trivia experiences over the holidays. While many bars host Christmas pop-ups, Graystone decided to change things up…with 8 Crazy Nights! A Hanukkah pop-up event unlike any other! And yes, they still have trivia on every Wednesday during the event, with specialty theme cocktails like the “Mensch Mule” and “Gelt Martini.” They also update their menu for the event for holiday-appropriate fare. This includes a variety of latkes, matzo ball soup, challah grilled cheese, and boozy jelly donuts (the last one isn’t quite a Hanukkah tradition, but this is a tavern after all).
A Space That Grew With Its Community
Graystone is not only a breath of fresh air in the otherwise crowded and occasionally unwelcoming venues in the Wrigleyville area. They offer a friendly staff, great service, neighborhood vibes and an incredible menu. They’re also home to many Whaddayaknow? events that our hosts have been able to enjoy.
We’ve hosted many team-building events at Graystone, including holiday parties, where the covered and heated patio area provides a spacious environment. Chi Hunter does his thing, providing impossibly smothered nachos, delicious wings, tater tots, and much more! After we’ve given out our yearly rewards to our amazing Whaddayaknow? hosts, we can assure you no one leaves with an empty belly.
Graystone is an amazing home base where you’ll always be welcome for a meticulously-crafted drink, perfectly-poured beverage, and a delicious meal. You can make friends in the calm of the storm that is Wrigleyville. There are so many amazing bars and taverns in Chicago, and we are lucky enough to work with Graystone and so many other great spots.
