As a parent and an American during an election year, I had to make all sorts of crucial decisions in 2024. The most difficult and important of all was which bike to bring with me on my summer vacation.

　　Each year at the end of August my family and I travel to Adirondack Park in upstate New York, where the cycling terrain includes paved climbs, gravel roads, and and rocky trails that disappear deep into the wilderness. Every spring, I start thinking seriously about which bicycle will have the privilege of accompanying me. The optimal choice is generally a rig wide of both tire and gearing, and past standouts have been my Rivendell A. Homer Hilsen and my Jones LWB.

　　This year I figured Id probably just bring one of those two bikes yet again, but at the very last second I made a bizarre and potentially foolhardy decision. Like George Costanza buying an 89 Chrysler LeBaron because it once belonged to Midnight Cowboy star Jon Voigt, I ultimately went with a 1998 Trek Y-Foil 77, on loan to me from the Classic Cycle collection, a historic bike museum and shop based in Washington.

　　Like the LeBaron, the Y-Foil 77 was also of highly dubious celebrity provenance, having supposedly once belonged to the late writer and bon vivant George Plimpton.

　　It may seem far-fetched, but Classic Cycle also sent a letter of authenticity to prove it that it was owned by the Paper Tiger author. Who am I to argue?

　　As a rider with traditional (some might even say old-fashioned) tastes who likes normal diamond-shaped frames made from metal and who has been one of the cycling medias most outspoken critics of the carbon fiber hegemony, Ive always found the Y-Foil to be absurdly outlandish. It was hard to imagine myself even riding the thing, let alone liking it. It seemed more like a triathlon bike than a road bike, which…eeew. Yet the more I rode it, the more I began to appreciate it.

　　Sure, the bike only holds one water bottle at a time, and yes, the void where the seat tube is supposed to be makes it look like a device made to bore holes in giant wheels of cheese. (The unorthodox frame design also makes sure you get every last bit of road spray should it rain.) But I rarely carry more than one bottle anyway. Despite its outrageous appearance it handles just as any well-designed road bike should, plus the beam design of the frame provides just a tiny bit of suspension which makes the ride surprisingly smooth and comfortable.

　　Trek only sold the Y-Foil for two years, in 1998 and 1999, and since then the bike has acquired a bit of a cult following—partially because theyre kind of rare and some people think theyre cool-looking, but also because of the aforementioned smooth ride quality, which is unusual for a road bike that only clears a 25mm tire. Id never been a member of the Y-Foil cult, and so I knew little about the bikes history, apart from vaguely recalling the design having been banned from competition or something.

　　So I started reading up on their history, and was surprised to learn that not only wasnt it a triathlon bike, but it had supposedly been designed with Paris-Roubaix and the cobbled classics in mind, and early versions even had a suspension-corrected fork. This explained the pinched-looking front end of the frame as well as the elongated fork crown, which Paul Johnson of Classic Cycle likens to a pair of high-waisted jeans.

　　The revelation that the Y-Foil was designed not for triathlons but for the cobblestones of Europe was almost harder to believe than the whole George Plimpton thing. So to find out for sure I reached out to Trek, who connected me with Jim Colegrove, a now-retired engineer who worked on the Y-Foil.

　　In the nineties, Colegrove told me, cyclists (or at least bike companies) were having a love affair with beam bikes. Trek was also having lots of success with their Y-framed mountain bikes. So the idea behind the Y-Foil was to bring the design over to the road and to take taking advantage of beam-maina.

　　As Colegrove and the team at Trek saw it, when it came to road-oriented beam bikes, Zipps 2001 model was the one to beat, though they also felt it had three fatal flaws: lateral deflection (they called it wag bob (the feeling that youre sitting on a diving board); and weight (the Zipp was quite heavy). So Trek set out to design a Y-frame road bike that would suffer from none of those problems. At the same time, they also saw an opportunity to incorporate a Rock Shox suspension road fork, which people at Trek were convinced was going to be a thing, as Colegrove puts it.

　　Not everybody on the team agreed, and of course suspension forks on road bikes didnt turn out to be a thing at all (at least not until gravel happened). Still, the 1992, 1993, and 1994 editions of Paris-Roubaix had all been won on Rock Shox forks. Trek planned to offer the new Y-frame road bike to pro teams, and so the suspension fork made it onto the bike. (Or at least the suspension fork compatibility did. Colegrove doesnt know if anybody actually ended up using a suspension fork on a Y-Foil, and Ive certainly never seen a squishy Y-Foil either in the wild or on the Internet.)

　　Alas, just as Trek launched the Y-Foil, the Union Cycliste Internationale, cyclings governing body, ruled that road bike frames shall be of a traditional pattern, i.e. built around a main triangle. This rule meant the pros wouldnt be able to ride the Y-Foil in any race under the auspices of the UCI, which is to say all the races that matter to people when theyre deciding which expensive road bike to buy.

　　Colegrove wonders if perhaps the UCI may have made the rule specifically to foil (see what I did there?) Trek in order to protect innocent European bike manufacturers from a big bad American company with the capability of producing futuristic aero bikes at scale. However, its worth noting the ruling affected European bikes too, such as the Colnago Bititan with its twin downtubes, so perhaps they really did just want to uphold tradition and spare us all from a nightmarish all-recumbent pro cycling future.

　　Of course there was still nothing keeping you from buying a Y-Foil to race a triathlon, or your local USA Cycling-sanctioned criterium, or just riding it for fun and enjoying the head-turning looks and aero benefits. (According to Colegrove the wind tunnel results showed the Y-Foil to be significantly more aerodynamic than a traditional frame.) But the bike industry doesnt work like that, and since the Y-Foil would never be seen under the winner of the Tour de France it had limited appeal and went into, as Colgrove puts it, a black hole.

　　Despite the aero factor it wasnt a true triathlon bike, nor would it ever have a pro cycling pedigree. While the bike did make it into production, the last year it appeared in the Trek catalogue was 1999—the same year Lance Armstrong won his first Tour de France on a stock Trek 5500 with a diamond frame.

　　25 years later, all of this lends the bike a certain pathos, and since I was enjoying the bike much more than I thought I would I figured Id bring it with me on vacation as sort of a consolation prize. Just across Lake Champlain  from New York State lies Vermont, a land criss-crossed with gravel roads, where the bike could finally taste the terrain for which it had been designed, yet few Y-Foils have ever experienced.

　　Road cyclists have recently embraced wider tires. With cyclists tackling roads with rougher surfaces, 25-millimeter tires—which is the widest a Y-Foil will allow—are now considered too narrow.

　　However, I made it through the roughest sections without washout or pinch flat, and otherwise the bike was not only competent but smooth, the beam offering just enough flex to allow me to comfortably shift my weight onto the rear wheel. Having successfully negotiated the gravel roads of Vermont, I rolled onto the ferry to Ticonderoga, NY.

　　Ticonderoga is steeped in history and the things that made this country great. Theres the eponymous fort, the eponymous pencil (they werent made there, but thats where the graphite used to come from), and theres the Star Trek Original Series Set Tour, which draws Trekkies from all over the galaxy.

　　At no point in our conversation did Colegrove mention the Star Fleet Insignia serving as an inspiration for the design of the Y-Foil, but I have to wonder if perhaps it crept in there subconsciously.

　　If youre a fan of technical innovation you may think we lost out when the UCI banned bikes Y-Foil, and if youre a traditionalist you probably think we dodged a bullet. Id certainly count myself as a traditionalist. But more than anything Im also a bike nerd. I can appreciate and enjoy this relic of what might have been.safe in the knowledge that it is no longer a threat to the supremacy of my beloved diamond frame.

　　The Y-Foil may not have been a commercial success, but Trek did accomplish what it set out to do, which was design a Y-shaped bike without wag, bob, or excessive weight that performs like a good road bike should. I enjoyed every ride with it on my summer vacation, and by choosing it I dont think I missed out on a thing…except maybe that second water bottle.