Windy City Smokeout
This past weekend I was at Windy City Smokeout, a country music and barbecue festival held in downtown Chicago… assuming that the parking lot near Grand Avenue and the Chicago River is downtown. I’m not a native, so I don’t want to declare anything “downtown” and upset any locals who insist that the Chicago Tribune parking lot isn’t really downtown.
While I was there, I saw a guy in his twenties take a drag on his vape pen and presumably try to do some sort of smoke trick with his mouth, but he was only able to exhale a messy smoke cloud that quickly dissipated. “There’s too much wind,” he exclaimed, defeated by his Juul mishap but still cheery. I saw a guy wearing a Chicago Bulls jersey (No. 24, for their productive rookie Lauri Markkanen) and a cowboy hat, one of many such pieces of headwear I encountered during those few days. Defining characteristics of this fest were that it was windy, there were Bulls fans, the folks had an affinity for country culture.
Derrick Rossignol for Uproxx
In high school, I was the obnoxious, my-music-is-holier-than-thou kid who wouldn’t be caught dead listening to country and would decry its merits at every opportunity. I’m not 16 anymore, though, and while country music still isn’t my go-to, I recognize its very real and legitimate appeal, an appeal that admittedly grew on me over the course of the weekend. Which is to say, Windy City Smokeout was an exemplary time, despite what my high school classmates probably remember about me.
I left most impressed by two acts. First there was Brett Eldredge, Saturday’s headliner and a local from Paris, Illinois. While I may not have been to as many shows as some of my colleagues, I can confidently say that Eldredge is one of the most energetic and charismatic performers I’ve ever seen live. The hometown hero angle may have gotten the audience extra amped, sure, but the fact remains that Eldredge knows how to get a crowd beyond lit. It was one of the loudest audiences I’ve ever been in, maintaining for at least two or three full minutes a decibel level that left cellphone videos of the performance unlistenable. The guy knows how to work a crowd, whether he’s just singing his songs, running around the stage to give everybody a good look at what they came to see, and shouting into the sky like he just struck oil.
Derrick Rossignol for Uproxx
It’s also absolutely worth noting that during his set, he brought his dog up on stage. The pair wore matching Cubs jerseys, did some tricks, and both were good boys.
Then there was Turnpike Troubadours, who drew me in with a southern rock- and folk-inspired sound that I wasn’t expecting. It was a delightful surprise that kept me in the photo/VIP pit for their entire set, despite my tendency that weekend to leave after the first three songs and find something else to explore. Whether or not you’re a “country fan,” these guys are just damn good. Truth be told, I don’t think I expected to leave Chicago with a new artist as part of my regular listening rotation, but a cursory exploration of their discography has so far confirmed that my initial impression of the group was spot on.
All that said, perhaps my favorite moment was also the most surreal: There were plenty of drinks on hand at the festival, one of them being John Daly’s Grip It & Sip It, an alcoholic version of an Arnold Palmer that the namesake legendary golfer decided to start selling. As I waited in the photo pit for Eldredge’s set to begin, a radio DJ or somebody like that took the stage to introduce “a legend,” a claim that left me skeptical. I quickly realized he was totally right, though, as Daly took the stage, red plastic cup in hand.
Daly, as well known for his colorful personality as he is his long drives, started asking the crowd about their current state of drunkenness, and in a move that definitely came as a surprise to the people up there with him, he enthusiastically and repeatedly implored women to remove their shirts. As somebody who has found Daly fascinating for a long time, I couldn’t stop laughing at his unrelenting party attitude.
Derrick Rossignol for Uproxx
The next day, Daly withdrew from the US Open due to issues with his knee, and my golf fan friend joked, “Sources say he’d much rather stay put at the Chicago music/BBQ festival instead of catching a flight to Scotland.” That was a funny Facebook comment to be tagged in, but maybe there’s something to it, because Daly sure did have a great time. A few minutes after he got off stage, he walked past me in the photo pit to enjoy Eldredge from the front row, which resulted in one of the more personally significant selfies I’ve ever taken.
Daly’s alcohol offerings were just a sliver of the consumables available since the event was just as focused on the food as it was the music. I can’t speak much about the drinks, since I’m not much for alcohol, but like everything else about the Windy City Smokeout experience, I’m sure it was delightful.
Derrick Rossignol for Uproxx
Festival food is usually fine, and sometimes even pretty good, but Windy City Smokeout taught me that fests could be doing so much better. (Although Stagecoach did an excellent job this year, recruiting Flavortown mayor Guy Fieri to curate their barbecue lineup). This weekend’s event brought in barbecue, ice cream, tacos, drinks, and other foodstuff from across the country, and it was a delight that went down smooth on a hot summer day.
I had a pulled pork sandwich from Chicago’s Bub City, ice cream from New York’s Big Gay Ice Cream, smoked short rib from Atlanta’s Fox Bros Bar-B-Q, cold-pressed juice from Chicago’s Real Good Juice Co., and other things that either fell off the bone or hit the spot. All of it was easily the best festival food I had ever had: The meats were perfectly cooked, the colder options were the refreshing kick I needed on a warm weekend, and I definitely didn’t rely on the store-brand protein bars that I usually bring to fests to keep me feeling lively between meals. I ate, and I was satisfied.
This was my first visit to Chicago, which in a way, is a bit of a drag: The weekend set over-inflated expectations for the experience I have the next time I find myself in the city (“The Windy Boy,” as I’ve taken to calling it) because it was a lot of fun. There was a lot to be satisfied about, because everything Windy City Smokeout tried to do, it did it exactly right.
Derrick Rossignol for Uproxx
I entered the event as a country outsider, and while I may have still left that way, I kind of wanted to walk out of there wearing a cowboy hat and a Markkanen jersey.
Uproxx was hosted for this story via accommodations provided by Windy City Smokeout. Check out the Uproxx Press Trip policy here.
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