Skateboarding in Chicago: Where parenting meets pavement

A few years back, when I turned 30, I was desperately looking for a way to recapture some of my carefree days of youth. So I bought a mountain bike, enrolled in a gym membership, and bought a pair of Chuck Taylors. All set, right?

Then I met Gabriel Allen, owner of Wilson Yards Skate Shop. The thought of getting back on a skateboard after 15-plus years was as exciting as it was frightening. I don’t know what happens with age, but the force of gravity seems to pull us down harder as we advance through the years. We forget how to fall, bruise deeper, and ache longer. All that being said I took the plunge and bought a board. Actually we bought two boards, one for me and one for our future little Tony Hawk. Leo was too little to stand on his I was too big to fall off of mine. The irony didn’t escape me.

Gabriel’s shop is fantastic. He welcomes skaters of all experience levels. He is helpful and will not sell you anything you are not ready for. I remember when we were debating about the purchase of Leo’s skateboard and Gabriel brought up the point that a cheaper board from a big box store is just as capable to learn on as a professional quality board from his. He was actually trying to save us money as opposed to selling us something we didn’t need! In the end we made the decision to shop “local” and buy from him and reward his entrepreneurial spirit.

Our skating adventures these last three years have seen their ups and downs. We love to go out on Sunnyside Mall and skate with some of the local kids in the neighborhood. Leo is now standing on his board at times and learning the ins and outs of balancing. I have spilled a few times but have avoided anything drastic.

My best story was skating with my brother under the bridge at Montrose and Lakeshore Drive. As I was heading west on Montrose, my board hit a rock and shot out from under me and took off in reverse off the sidewalk and straight out in to the street. Just then a woman turned off of LSD in an SUV and ran right over my board. Oh the humanity! Not to worry though my board survived with just a broken wheel. Take that SUV! I took my board to Gabriel and he had a new set on in just a few minutes no embarrassing questions asked.

Looking for a board for you or the kids? Visit Gabriel @ Wilson Yards Skateboard Shop, 1354 W Wilson Ave, Chicago, Il. 60640, (773)561-2406

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