Afew minutes after 1 PM last Saturday, Ian Hunter sat on the concrete steps outside Club Lucky in Wicker Park, panting. “I am definitely going to barf,” he said, lifting his helmeted head from his hands. “I don’t know if it’s from the drinking or the running. I’m guessing it’s the combination.” Hunter, 30, was a member of Runaway Bride, one of 22 teams competing in the first-ever Chiditarod, a shopping-cart race-cum-pub crawl that stretched from Wicker Park to the Hideout on West Wabansia, with contestants collecting nonperishable food for charity along the way.

“We started planning it about six weeks ago,” said Jake Reimer, one of the organizers. “None of us had ever done anything like this before, though most of us have been to Burning Man, and some of us ride in Critical Mass.” Reimer, 30, had heard about similar races in Brooklyn, San Francisco, and Portland, but he said the food-drive aspect of the Chicago version was unique. “Our main goal is having fun, but we figured as long as people were running around with shopping carts anyways, we might as well get them to put food in them.”

Up until a couple weeks before the event, it looked like the Chiditarod would be nothing more than a disorganized mess. On the official Web site the race’s start time was listed as “between 11 AM and 1 PM,” the length of the course wasn’t given, rules were few and loose, and prizes were speculative at best. The registration page suggested entrants with cell phones might receive text-message updates about course changes during the race. With one week to go, the Chiditarod MySpace page had attracted a mere 31 friends. “We had no idea how many people were going to enter. We thought if we had ten teams, that was success,” said Reimer.

But by noon on Saturday, at the close of registration, there were more than 100 participants swarming the parking lot of the Pontiac Cafe on Damen, and spectators were standing on cars to capture the mad scene on their camera phones. As the start time approached–it was eventually nailed down for 12:30 PM–members of the Biking Vikings made their final preparations, drinking Sparks and pulling women’s Speedos over their black sweats. “I’ve never done anything like this before,” said Matt Weber, the Vikings’ coach, as he got into uniform. “You know, actually worn a women’s swimsuit.” His job was to run alongside the team, providing motivation by blaring Jock Jams through a bullhorn he’d attached to an iPod.

Each team consisted of five contestants: four “dogs” who pulled the cart with rope and one musher, who handled the steering. In addition to the $5 per person entry fee, teams also had to provide their own shopping carts, which they could then modify and decorate. The race involved two mandatory pit stops of 20 minutes each–at Phyllis’ Musical Inn and Club Lucky–but otherwise there was no designated course. And before crossing the finish line at the Hideout each team had to collect at least ten pounds of food, which they could either pick up along the way from their own hidden caches or have delivered to them by friends. Participants weren’t supposed to start the race with food in their carts, but it didn’t seem like any of the referees were actually enforcing the rules. In fact, bribing and cheating were openly encouraged. The Vikings, who’d turned their cart into a cross between a ship and a shark, had hidden groceries in the hull.

After a final review of their planned routes, teams jockeyed for spots at the edge of the parking lot and sidewalk. With a wave of Reimer’s flag and the sounding of a trombone they were off, with the majority scrambling east through Wicker Park. Most were equipped with boom boxes playing the Chiditarod theme song, “Eye of the Tiger,” though team Double Dare dominated by blasting Europe’s “The Final Countdown” as they blazed past the dog park and headed for an alley shortcut to Wolcott.

At Phyllis’ the teams had their race cards marked with their entry and exit times, though some were able to shave off a couple minutes by bribing the timekeepers with shots and Guinness. Runaway Bride, who had dressed as a wedding party and were mushed by Cynthia Castiglione, the bride, arrived first, despite hitting a tree en route. Their cart sported new wheels, a steering mechanism, a mush platform, and the front suspension of a ’73 Combat Wombat. “I trust our cart,” Castiglione said as she sipped her beer at the bar. “I’m not going to spend $30 getting judges drunk just to get a minute off our times.”

But by the time they’d arrived at Club Lucky, Runaway Bride’s morale was flagging. They’d taken a wrong turn down a dead-end street and fallen way behind, and nausea was starting to set in. The Biking Vikings, deciding to pace themselves, avoided the bar and stood around smoking cigarettes outside. Most of the teams were met by friends delivering canned food, and some performed in the talent-show portion of the event. For their rendition of the Chiditarod theme song, the Palmer Park Freedom Funk 5 won “Best Use of ‘Eye of the Tiger.'”

Just under an hour after the start time the teams started to cross the finish line. The bathrobe-clad Captain Slam and the Four Hodags came in first, followed by Runaway Bride and the Vikings, who won the award for “Best Shark Cart.” “I feel terrible,” said Vikings musher Matt Walker, a 25-year-old U. of C. grad student, as his team drank beers next to their cart. “I’ve never run this much in my life–ever.” Perhaps the only team feeling good at the end was Pony Up, a collection of tutors from 826CHI, who finished next-to-last after walking the entire way in just under two hours. Dressed up like cowboys with thick mustaches, pushing a cart done up like a horse, they wound up winning “Best in Show” even though one of them kept getting nosebleeds along the way.

Overall the event brought in 938 pounds of groceries; one team, the Haz Mat Rats, managed to tow 185 pounds across the finish line. All the food will be donated to Vital Bridges, a local nonprofit that provides support for people affected by HIV and AIDS. When asked if the haul would be a tremendous help for the organization, communications manager Tom Hartman replied, “That depends. Not if it’s 938 pounds of marshmallows.”

Art accompanying story in printed newspaper (not available in this archive): photos/Joeff Davis.