Natty Bwoy Bikes & Boards Makes An Impact Through Skating on Chicago’s South Side
As I drove into the city, I was hit with a long patch of heavy rain — the kind that veils the usually striking skyline view. It wasn’t the nicest day Chicago had ever seen — some may have considered it gloomy. I arrived in Bronzeville and parked, the sky still grey with dense clouds. I walked up to Natty Bwoy Bikes & Boards and met Kahari Blackburn, who runs the shop with his brothers, Kari and Katon. All of a sudden, the block seemed to light up.
Natty Bwoy Bikes & Boards operates out of a shipping container, part of the Boxville marketplace in the Bronzeville neighborhood of Chicago. Boxville is innovation at its finest — a collection of shipping containers converted into affordable retail space that allows budding entrepreneurs like the Blackburns to turn their dreams into realities. Much like the marketplace it calls home, Natty Bwoy is the first of its kind — it’s the only skate shop on the city’s South Side, opened in late 2020. Before Natty Bwoy opened, if a kid in Hyde Park or Bronzeville needed a new board or a simple bike repair, they’d have to venture downtown or to the suburbs. Part of the joy of skateboarding or bike riding is the sense of freedom it brings — something the Blackburns understand well.
“As kids, it allows for you to just move at your own pace,” said Kahari. “You can do your own thing. You’re not asking a parent for a ride. I think it’s a nice luxury and privilege and I hope for more kids to be able to have it.”
A free library comprised of donated books sat at the shop’s entrance, allowing for kids to take a new book home with their board. Decks, wheels, trucks, and tape were spread out among boxes, and Natty Bwoy and Natty G’yal t-shirts hung on display. Vans and Nike SBs — new and old — were stacked and waiting to assist in the landing of a kickflip. Need to get that rusty chain fixed? Bring it around to the side.
The goal is to get kids in the community riding bikes and boards, assist with repairs when needed, and help them foster their newfound passion through free skate lessons and group bike rides. But in my initial conversations with Kahari and those around the shop, I quickly recognized that Natty Bwoy goes beyond the boards — it’s about community, organization, and a genuine ambition to make the neighborhood a better place. The waves are already being felt.
“We feel a presence of gratitude,” said Katon — the skater of the family — during a phone conversation. “We feel that people are joining — parents are happy that we’re doing it. It’s been fun, it’s definitely helped us build a community within our neighborhood.”
Kahari and I moved to a third-floor balcony for a more “formal” interview. All of Boxville was in sight below — more shops opened as curious customers peeked around. Natty Bwoy was in clear view. “I have a good friend who came up to the shop last summer,” Kahari told me. “The direct thing he said was, ‘Dang, I wish we had this as kids.’ And I was like, ‘Damn that’s crazy,’ because we’re definitely doing this because the kids right now could use it.”
“It’s cool to have the retail part where we are making money that obviously pays for any free things we’re doing,” said Kahari. “But at the same time, having free shoes, free books, free clothes, free helmets — those types of things — I think really puts a smile on people’s faces. Especially a kid. There are shorties that walk in all the time like, ‘Dang, bro, I wish I had that,’ and we’re just like, ‘Nah, bro.’ This shit is abundant — everyone has more of this than they need anyway, so why not give it out to people?”
Kahari spoke of future iterations for Natty Bwoy, whether that be expanding into a brick-and-mortar location or constructing an indoor skatepark. The monetary gain and expansion possibilities of a thriving business would be welcomed, but that’s not the end-all-be-all. Each of the Blackburn brothers is an artist in their own right, understanding that art is a vehicle for expression that can guide someone — especially a kid — to find their true self. At the end of the day, Natty Bwoy uses skateboarding to set young skaters on the path to being themselves — a sentiment that is often heard, but tough to act upon.
“I read this quote — there’s a book that we have in there called Skateboard — and it’s basically saying that skateboarding is closer to an art form than it is a sport,” said Kahari. “Because it’s about your own personal journey, right? It ain’t necessarily always about the comparison of where you’re at versus someone else. And even in the internet age, I think it’s so easy to be constantly always looking at how to measure ourselves. That shit is toxic, bro — it’s unhealthy. So with the shorties, I think we try and be as open, easy, and welcoming as possible.”
The following Sunday, I drove back to the city and arrived at Kenwood Park Playground to observe a Natty Bwoy skate lesson. The weather was a stark contrast from days earlier — it was hot. I approached the blacktop where the lesson would take place, greeting Kahari and meeting Kari, as well as a few older skaters.
One-half of the blacktop was dedicated to the lesson. Packed with an army of knee pad-wielding kids just learning how to push, instructors showed the new skaters how to get started as their parents held court around the blacktop’s edges. On the other half, older skaters competed in games of S-K-A-T-E, traded skate stories, and attempted to land new tricks, all while seemingly to simply enjoy the fact that they were spending their Sunday afternoon atop their boards.
“There’s this one family that biked all the way from up North to come down to the lesson, which is really cool,” said Katon. “It’s always sick to build more of the community, especially with the skaters in the city. We have kids who we’ve been skating with for about a year now.”
I spent the majority of my time observing the lesson. It didn’t take long to realize that what I was witnessing was community in the truest sense. Everyone — skaters, instructors, volunteers, parents — was in this together, for a shared love of their neighborhood. “Parents have definitely been the most adamant in all of this,” said Kari as we watched the skaters from a nearby bench. “They’ve formed committees and email chains and talk to aldermen, stuff like that. That’s been great in helping us organize and make this bigger every Sunday.”
The Blackburns’ dedication to their goals and their neighborhood was evident during the lesson as they handed out snacks and water while fielding questions from inquisitive kids. Positivity radiated from all around — it was inspiring. Throughout the day, I heard mentions of numerous projects that featured any one of the Blackburns’ involvements, including a free arts and sports camp, individual artistic endeavors, a Timberland campaign, and a petition to repave the blacktop used for skate lessons.
“We love it, we enjoy it,” said Kari. “It feeds our own passion for it because we just do it for fun. And the fact that so many other people enjoy the same thing for fun, it’s really great. I just hope it leads to bigger and better things for the brand and everyone else in the community. Like next summer, we might have an actual summer camp or something like skateboarding summer camp, because this is showing us that there’s a need and a want for it. It just takes us putting our heads together and doing some programming.”
Although my time with the Blackburns was brief, I still find myself thinking about the interactions one month later. I’d never spoken with people so willing to give back, so eager to make a change. Their goals are within reach, whether it be a blacktop mural or more resources for young skaters. The community is clearly behind Natty Bwoy, and as their efforts are further recognized, it won’t be long until it’s the entire city.
It’s so easy to become bogged down by the constant flurries of negativity that appear each time we unlock our phones and scroll through our feeds. Yet when you have conversations with people like Kahari, Kari, and Katon, it doesn’t take long for that to wash away. Change doesn’t happen overnight — it takes real work, and if anyone is going to put in the time, it’s the Blackburn brothers.
