Gangster rap: an interview with bike style icon Lorena Cupcake

Lorena Cupcake

[This piece also appeared in Checkerboard City, John’s weekly transportation column in Newcity magazine, which hits the streets in print on Wednesday evenings.]

In a Midwestern town where folks dress conservatively, bike style icon Lorena Cupcake stands out like a handful of Skittles scattered across the Wall Street Journal. Easily spotted by her candy-colored outfits, rainbow-and-lollipops tattoo and messenger bag emblazoned “Cupcake Gangster,” she’s also an astute commentator on the local cycling, drinking and foodie scenes via her frequently updated, often hilarious Twitter feed.

But Cupcake, 25, is far from just a hipster gadfly. A frequent participant and volunteer at “alleycats,” underground, messenger-style checkpoint races, she runs the bike event Twitter calendar @chicagoholdup and helps stage the annual Bicycle Film Festival. Last year she and a few other petite fixed-gear enthusiasts formed Tiny Fix, a bike gang especially for women under 5’2”, which organizes bar nights, dance parties and now their first alleycat, last weekend’s Tiny Fix Ace Race.

I recently caught up with Cupcake, fresh off her day job as a bank teller, over $3 cheeseburgers at the Blue Frog, a messenger bar at 676 N. LaSalle in River North. She gave me the skinny on Tiny Fix, the upcoming race, and the things she loves and hates about biking in Chicago.

How did you get into biking?

All my biking as a little kid was done on a Teenage Mutant Ninja Turtles mountain bike or on my little brother’s mountain bike to go get cigarettes as a teenager. I wasn’t serious about it all. And then about three years ago I bought the world’s crappiest 1960s-knockoff Stingray cruiser. Now I know it was way to small for me and it was just the jankiest bike of all time. But I started riding it, and then I started riding it a little bit further and then I was able to justify buying a decent bike. And then I rode that a little bit further and started to get more into the bike scene. And then I was able to justify buying what everyone rides basically, the fixed-gear that I can lock up anywhere. I made it, I guess. I’m not a big dork on a little stingray anymore.

So what kind of bikes do you have now?

I have a Specialized Globe Live 1 mixte. I think of it as the garbage barge. I just use it for groceries and hauling my dog around because it has a giant front rack on it. I have my Jamis Sputnik fixed-gear which is more of a loose concept because I keep breaking it, crashing it and having all the parts stolen, so it’s just a constant revolving door of parts and frames.

What’s your involvement with the local bike scene?

I’m just a girl who kept showing up. I kept going to events until I knew everybody and that’s it. As far as getting into a more proactive role and throwing events, what happened was I was joking with some friends about starting a bike gang. There’s KC Winter, Karen “Kaz” Altes and Anna Titcomb. And we were like, “Oh, we’ll be the tiny girls on fixed-gears gang.” To my surprise we didn’t just joke about getting knuckle tattoos, we actually built a website, had a bar night, and started getting involved with people.

What are the goals of Tiny Fix?

We want everyone who rides bikes in Chicago to have more fun. It’s not about a certain group or only the cool kids. We want to make fun s— happen. Two, we want to make the world a friendlier place for female cyclists, specifically, petite female cyclists. I really hope that someday somebody running a bicycle company or a bicycle apparel company finds Tiny Fix and says, “Holy S—, there’s all these girls out there who are under 5’5’’ who ride bikes and would buy our products if we actually made them their size. If you’re under 5’5” or have to ride a 47 cm frame or smaller, you’re options are really limited.


Do you race yourself in alleycats?

I don’t do speed races because I’m not that badass. But I have worked checkpoints at multiple Downtown Shakedown races. I have ridden the Sadie Hawkins ride. I raced in PolCat. I checkpointed Wrigley Dash. If I have a friend who’s throwing an alleycat and I don’t want to race it, I always offer to checkpoint it.

Tell me about your upcoming alleycat [the race took place last Saturday, May 26].

The Tiny Fix Ace Race is an alleycat that absolutely anyone can have fun at. It doesn’t matter if you are the world’s fastest messenger who knows the Chicago grid like the back of your hand, or if you have the creakiest, busted-ass Schwinn cruiser from 1963, you can still race this race to the best of your ability, win a ton of prizes and have a ton of fun and feel challenged at the same time. There is a speed race, which is a traditional alleycat. You’re going to be racing about 25 miles in two hours, and the fastest person wins.

There’s also the Poker Ride, which is a ride of about ten miles in two hours. It’s no pressure, and you don’t have to run any reds or act real crazy. You just have to hit five checkpoints and collect a playing card at each one. And then at the end of the race whoever turns in the best poker hand is the winner. So it’s more about luck and having fun and hanging out and participating than it is about who’s badass. It’s not a d— measuring contest.

I was a messenger in Chicago for six years, a long time ago, but the current alleycat scene flies totally under my radar. How do people hear about the races?

It’s all Facebook. People try not to publicize things too much because they’re illegal.

What your favorite thing about biking here.

The people. Sometimes I can ride my bike into work and I’ll see four different friends, also riding their bikes. My boyfriend’s a messenger and that’s how I met him. I wouldn’t have ever met my best friend if I hadn’t met him at the Bicycle Film Festival, so I love the way biking brings people together.


What would you like to see improve.

I want all the grated bridges covered. That’s my big pet angry. They’re not fun on a bike with skinny tires. I think they’re a safety hazard and I would much rather see every grated bridge covered than another inch of protected bike lane go in. I just think it’s a higher priority. I know it’s an engineering thing because some of the bridges can’t carry extra weight, so it’s not as easy as slapping steel plates on them. But if the city is really serious about making improvements to bike infrastructure, I want to see that fixed.

I’d also like to see more people doing what Tiny Fix is doing and throwing events. Anybody who has a bike, an Internet connection and a group of friends can be making awesome stuff happen.

[Here’s Lorena’s List: the Cupcake Gangster’s favorite Chicago folks, bikes, bags, threads, drinks, eats and cakes.]


“I really admire the Cycle Messenger World Championships crew. Those kids have been throwing events in Chicago since before I moved here and there are a number of women involved who are every bit as integrated as the men. There’s Christina and Allison Peck – they’re twins – and Nikki Munvez. They’re super-badass.”

Bikes (for petite women)

“Decent ones? Jamis, Fuji and Wabi make fixed-gears that are 47 cm or smaller, and I wish I could afford a Gunnar Street Dog – it’s an awesome option. There are girls out there who are smaller than me for sure and I really don’t think they should not be allowed to ride bikes or be forced to ride some kid’s Huffy because they’re short.”


“My messenger bag’s made by Seagull Bags, out of Columbus, Ohio. I love them.”


Sock it to Me makes the world’s best knee socks. PF Flyers make really awesome sneakers that have a stiffer sole than Converse and I think they’re more stylish and I just like them way better for bike riding. Thrift stores. Maxwell Street Market is great for really ridiculous cheap club wear that you can haggle with the guy over. I got this lime-green crop top with silver lamé cheetah print on it.”

Drinks (biker bars)

Blue Frog on LaSalle on Thursdays for the $3 burgers. There’s always a group of messengers here chomping on cheap burgers and shooting the s— with Cliff, the bartender. There’s Cal’s Liquors downtown, any day of the week but especially Mondays because it’s $2 PBRs. If I get out of work and I don’t want to ride home yet I got to Cal’s. Handlebar [a Grid Chicago sponsor], especially for the vegans. Boiler Room – it’s $7.50 for the PB&J – that’s a slice of pizza, a PBR and a shot of Jameson. For people who burn a lot of calories, eat a lot and drink a lot, that’s a good deal.”



“I’m not vegan but my best friend is, so I go to Dharma Garden for affordable, BYOB Thai food which is either vegan or not. When I want to go fancy, I love Longman & Eagle. There’s Original Rainbow Cone in Beverly. You ride your bike for 15 miles and then eat this ice cream cone and it’s the best ice cream cone you’ve ever had because you just rode your bike 15 miles, just for ice cream.”


“The Flirty Cupcakes truck is great because they saw my messenger bag and they were like, ‘Hey, you, that’s awesome.’ And then I showed them my I.D. that shows that my legal middle name is Cupcake. And they’re like, ‘Alright, free cupcake for you, Cupcake.’”

Published by

John Greenfield

John has lived in Chicago since 1989 and has worked a number of bicycle jobs, from messenger to mechanic to managing the Chicago Department of Transportation's bicycle parking program, arranging the installation of over 3,700 bike racks. He writes regularly for Time Out Chicago, Newcity, Momentum and Urban Velo magazines and works at Boulevard Bikes in Logan Square.

15 thoughts on “Gangster rap: an interview with bike style icon Lorena Cupcake”

  1. i can totally relate!  being 5’2″, it’s tough to find a new bike when all the manufacturer’s smallest size is 49cm, even supposedly women’s frames.  vintage women’s bikes built with smaller wheels were the only bikes that seem to fit.  i’m not into riding fixed gear unfortunately.

    1. You don’t need to ride a fixed gear bicycle to be a member of the Tiny Fix Bike Gang. 

      Cupcake says, “Everyone is welcome to participate in events; membership is limited to people who REALLY want to work with us, as in, willing to email sponsors & write blog posts & come to meetings & everything, we put a ton of work into the Ace Race”.

  2. I sure hope the bike style queen wears a helmet.  I see way too many bikers out there with no helmet.    Do they really think they will never be doored or otherwise meet up with a car?

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