As I sat, sweating, at a keyboardless iMac in a sweltering bar, an amplified voice announced the beginning of competition: "The previous rounds were based on a combination of luck and skill, but this one is really all about skill. Can you surf? Can you rip?"

The announcer was Zachary Kaplan, community manager at the contemporary arts organization Rhizome. Ordinarily, Kaplan explained earlier that day, Rhizome is based at the New Museum in downtown Manhattan, but for a few hours on Sunday, it was inhabiting the Rockaway Beach Surf Club, a tiki bar boasting watermelon margaritas and surfboard lockers, just blocks from the roar of the Atlantic Ocean. What better venue for Trailblazers NY, New York City's first competitive internet surfing tournament?

Trailblazers—which began in Stuttgart, Germany, in 2010, and made its stateside debut this week—asks competitors to get from point A to point B, across the vastness of the internet, using only the inline links embedded in websites to navigate. With no keyboard, we couldn't access the URL bar or search engines, and the browser we used wasn't outfitted with modern luxuries like bookmarks or a back button. We were to surf the web manually, site by site, click by click.

I signed up the week before at the urging of Dragan Espenschied, director of Rhizome's digital conservation program and co-creator of the Trailblazers concept. The game, he told me, was about conserving the idea of web surfing as a "folk ritual," while exploring the hidden power structures of the internet. He offered this scenario as an illustrative example: imagine trying to travel from Apple.com to an Adobe Flash download page using only links. Apple famously treats Flash with a mixture of ignorance and flat-out contempt, publicly railing against it and blocking its installation on iOS devices. What would it take to escape the internet universe of Apple—which mostly just links back to Apple—and enter that of Adobe?

If that kind of corporate boundary-smashing equals big-wave internet surfing, the first round of competition felt more like boogie boarding: each of us was given a list of three items to find on Amazon, and whoever added the most items from their list to the shopping cart within three minutes would advance. I successfully grabbed two of my targets—a cat litter box and a pack of Huggies diapers—and emerged from my bracket victorious. (Some items on other entrants lists: an HTML manual "of at least 300 pages," a Disney's Frozen-themed blanket, a Beyoncé album on vinyl, "sex furniture," Bill O'Reilly's Killing Jesus. I counted myself lucky.)

To size up the competition, I talked to a few other surfers who'd also won their first round. "I'm secretly super competitive, so I immediately started shaking with adrenaline," said Martha Hipley, a net artist. Austin Muller, a surfer with a mustache and a grimy lime-green baseball hat, agreed: "It's all a blur now. The adrenaline was pumping." Said Matt Jastremski, a United States Coast Guardsman whose impressive build stuck out amongst the throngs of bloggers, artists, and UX designers: "I feel vindicated. Thousands and thousands of hours online have finally paid off."

Round two was considerably more difficult. My heat of competitors was asked to navigate from callahead.com—homepage of New York's "leader in quality porta potty equipment and superior cleaning service that cannot be matched"—to the website of the Frieze Art Fair, which had reportedly enlisted Callahead's services during its latest installment. Before the competition, Espenschied had given me a hint: though most seasoned internet surfers are accustomed to ignoring banner ads, they can be a Trailblazer's salvation. How to get out of a site like Amazon, whose only objective is to have you buy stuff from Amazon? Click the banner that's languishing at the bottom of the homepage, and a new frontier opens before you.

But Callahead offered no such outs. Everywhere I looked, there was only more Callahead—each link a trap door, leading deeper and deeper into a labyrinth of Luxury Restroom Trailers and Regal Berry Portable Toilets. After several minutes, I found my escape: the company's press page, which linked to a third-party site hosting its press releases. From there, I was off to the races, but by the time I arrived at the homepage of New York's Public Art Fund, hoping for a mention of Frieze, our 10-minute period was drawing to a close. No competitor had reached the goal.

We entered extra innings: whoever found an image of a globe, any globe, anywhere on the internet, would be declared the round's winner. As I fumbled around, hoping the Art Fund had financed some work of globe-based art, I saw my undoing starting to load, pixel by horrible pixel, on the next screen. Hipley, seated to my left, had reached Google Maps, and was zooming out as quickly as her browser would allow. Eventually, her monitor displayed all seven continents—a Google map of the world—and I was out.

My consolation prize was a zine by the artist Cory Arcangel, whose "mainstream non-aspirational (in)activewear" line Surfwear acted as the event's unofficial sponsor. Surfwear's motto: "Everything you need to chill in bed all day and surf the net."

Surveying the remaining competition, two stars emerged. On one side: Hipley, looking like freewheeling internet culture personified in a fanny pack and sumo wrestler t-shirt. On the other: Joe Puglisi, her corporate counterpart, in jeans and a button-up shirt. Hipley runs a difficult-to-navigate Tumblr and exhibits artwork at venues like the late 285 Kent in Williamsburg; Puglisi works in the sponsored content department at BuzzFeed. Given Trailblazers' artistic and political subtext, an observer inclined toward symbolism might see the duo embodying opposite sides of a tiny battle for the soul of the internet: art vs. commerce; lo-fi GIFs vs. hi-def photo sliders; seapunk vs. 13 Pop-Punk Heartthrobs, Then and Now. (The two other representatives of the corporate internet—myself and a reporter from The Verge—were both eliminated early on.)

Several more rounds played out—Sega.com to the Bad Sonic Fan Art Tumblr, Airbnb.com to rentistoodamnhigh.org—and Hipley and Puglisi continued claiming victories. Hipley, like most other competitors, employed an organic, improvisational style, while Puglisi proceeded with ruthless efficiency. As he told me later, he'd arrived with a strategy: get to Twitter's profiles directory, where he could browse an A-Z list of users, at all costs. His targets, he reasoned, were probably on Twitter, and their profiles likely linked to their homepages.

"The strategy was to find a central hub where you could conceivably get to any single page on the internet by clicking. And that's what we were looking for," Puglisi said, noting that John Urquhart, a fellow competitor and BuzzFeed employee, had conceived the tactic. "I'm surprised that we came in here and not many people had a hard strategy on what they were going to do." Like UNC basketball's vaunted four-corners offense, the Twitter directory was devastatingly effective, at the expense of some of the tension at the heart of the game. While other competitors struggled to make sense of a big, confusing internet, Puglisi simply clicked through a list until he found what he wanted.

It worked, however, and after two hours of competition, Puglisi and Hipley faced off, one-on-one, for the Trailblazers NY championship. Their task: to travel from Facebook, back through the annals of the internet, to Myspace, its clearest antecedent. Hipley, for all her past victories, was no match for Puglisi. In minutes, he'd gotten to Twitter, then the directory, then @Myspace. He clicked the link to Myspace.com in its bio, then rose from his chair, fist-pumping in celebration, before the page finished loading. His brief victory speech: "I am a BuzzFeed employee. BuzzFeed won this competition."

[Illustration by Jim Cooke]

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