
Winter in Toronto has a way of stripping the excitement out of life. The days are short, the conditions are frigid, and oftentimes I lack motivation to step outside to go shopping, let alone go for a jog.
But, when I heard that the Chipotle x Strava City Challenge running event was headed to Toronto this past January, my motivation to get outdoors spiked. I got my running shoes out. I was prepared to suffer.
For anyone unfamiliar with the Chipotle City Challenge, it’s a somewhat ridiculous but tempting ordeal for runners. The Mexican eatery gifts the runner who records the most laps around a specific Chipotle restaurant in a months time free burritos for a year.
You read that right. Free food for a year. For any runner, this is like having an unlimited supply of gels at mile 20 of a marathon–except dressed in foil with extra guac.
Chipotle Helped me Kickstart my Spring Marathon Training
I couldn’t resist the prospect of free food. It seemed like the perfect antidote to winter blues—and, of course, a fun way to kickstart my spring marathon training.
At first, I approached the challenge with casual intention. I participated in Chipotle’s kickoff event on January 2 where I ran a few laps around the location at the heart of the challenge, asking other runners how many laps they thought they could run during the month. During the first few days, I ran between six to ten laps a day to keep things chill, and scout out the segment and my competition.
It was sometime around Day 5 of the challenge that my burrito campaign really kicked into overdrive. Running around Chipotle was no longer a joke. I mentally decided to absolutely shred the challenge into beef barbacoa.
A Legend is Born (So I Thought)

I quickly claimed the title of “Local Legend” on Strava—a designation given to the man or woman who completes the most recorded workouts on a stretch of road or trail. By mid-January, I was averaging 40-50 miles each week around the restaurant.
Let me tell you, this was not an easy athletic feat. The Chipotle in question is located in the heart of Toronto, near the city’s main train station. The sidewalks are slammed with pedestrian traffic at all hours of the day. The lap itself is a tight 1,000-foot city block. Every lap felt like a mind-numbing carousel ride through car exhaust and past bewildered pedestrians, while inhaling burrito-scented air. I started my day with a morning run between 7 and 8 a.m. I’d return each evening to complete more laps between 5-7 p.m.
By the final week of January I had logged around 400 laps around Chipotle, which equated to 150 miles. According to the data on Strava, I was comfortably in first place. In fact, I had a 150-lap lead on the second-place runner heading into Jan. 31. Victory seemed inevitable at this point. My girlfriend and I went to the Chipotle on the final day to snap some celebratory photos. I even made a homemade crown.
An Undercover Victory
But then, as the final hours ticked off, my victory fell apart. As it turns out, I was undone by cunning Strava trickery. Another runner, who I will title Mr. Tricky Tactics, outwitted me.
Back on Jan. 21, this runner wrote on his Strava account that he was withdrawing from the Chipotle x Strava challenge due to a hip injury. He posted the news alongside a photo of him receiving acupuncture on his hip. At that point there were four serious contenders—myself included—who were vying for the title. We all thought the guy was done for. But he wasn’t.
In the final days of the challenge, he returned to the Chiptole and ran hundreds of laps, undercover. He waited to upload the data from those runs to Strava. So, those of us who were following the leaderboard didn’t know he was secretly amassing amazing mileage. He ran 110 miles in the final ten days, even sprinting a personal best 15-kilometer split just a few hours after he announced his injury.

We all learned about his impressive running feats when he uploaded his mileage from those ten days to Strava in the final hours before the deadline. I was blindsided! I wondered how the heck he’d run so far.
Considering I spent the last three days of the challenge running around that Chipotle, I couldn’t fathom how I’d been outsmarted. During those last ten days, I ran between 8-10 miles each day. I was out there at dawn running through snow and ice. I never saw the guy.
The Hard Lesson I Learned
I protested the result to Chipotle. Their response was diplomatic but logical: “He employed unique tactics.” Technically legal? Sure. Morally sound? Up for debate. But their decision was final. My foe had “employed unique tactics” and, of course, ran more laps than I had. The free burritos weren’t mine—they belonged to him.
The hardest part was that I was so confident in my strategy: rack up a huge lead early in the month and do anything to defend it. If I’d known my nemesis was still running, I believe I could have run big miles on the final few day to win. I would have gladly endured 24 hours of running if it meant scoring free burritos for a year.
But hindsight is 20/20. Instead of earning a year’s worth of guac, I instead learned a lesson in trust. Don’t trust everything you read online, and always be prepared for soul-crushing tactics when you’re chasing a Strava challenge.

Marley Dickinson has been a staff writer for Canadian Running Magazine for five years. He has covered events ranging from Jamaica’s Reggae Marathon to the Paris Olympic Games. Beyond running, Marley is a diehard Toronto Blue Jays fan and shares his love for baseball on his website BlueBirdTalk.
The post I Thought I’d Run Far Enough to Win Free Burritos for a Year. I Was Wrong. appeared first on Outside Online.