The Yale-Vassar Bike Race

The Yale-Vassar bike race found its origins in a drunken wager. At a meeting of Yale’s Trumbull Beer and Bike Society, one student declared he could beat another in a bicycle race all the way to Vassar. However, this valiant duel between two determined Trumbull residents quickly became a popular annual tradition in the early 1950s and a day on which the iconic style of the Seven Sisters and Ivy colleges revealed a sense of humor.

Each April, there was a Yale mass exodus, with around sixteen five-man teams pedaling the some 70 miles from New Haven to Poughkeepsie, eager to be reunited with their “waiting Vassar femmes.” The rules? First team to Vassar won, fancy dress optional but preferred, and, to make things just a little bit more interesting, at each change-over on the relay one team-member had to guzzle a quart of beer before the next man began cycling.

While Yale and Vassar had long since enjoyed an academic connection, the 1950s saw this relationship become even more important socially. Vassar’s resident Warden, Elizabeth Drouilhet, remembered that in the early 1950s, “Students felt that they were totally isolated from the opposite sex. There were any number of attempts to try to counteract our geographic location.” Namely, there was the introduction of Vassar-Yale mixers and dances, however neither school actually sanctioned the race. Drouilhet described the race as a way for restless students in the post-World War II era to prove “what absurdities one could get into.” While over at Yale, Dean Harold B. Whiteman simply reasoned that, for the men at least, “I think this type of exercise a great deal better than face slapping or eating live goldfish.”

For those men who completed the race (and by all accounts injuries, exhaustion, inebriation and even simply disorientation hampered many efforts), their costumes poked fun at both the typical look of the Yalie and aspects of Yale history.

Present were the madras and khaki Bermudas, socks, loafers and saddle shoes, but with comedic accessories: one team adopted college ties, moustaches and bowler hats and still managed to complete the race. Another team fashioned a “Yale News Press-Cycle” and, complete with comedy goggles, flat caps and raccoon coats, and pedaled their way into Poughkeepsie. The more athletic teams in ’52 (although only one team actually trained for the race) even created their own sports uniforms emblazoned with team names like “The Over SEX-ted” or “The Maidenform Five.” And in later years there were the “Papa Peacocks” and their supporters “The Sex-Tots.”

But the girls also enjoyed a good time, and while some wrapped themselves in polo coats due to the April chill, wearing Yale scarves and waving blue and white pennants, others adopted outrageous fancy dress that paid homage to Vassar’s history. One year two girls arrived as “Mr. and Mrs. Vassar Brew,” dressed in 19th-century costumes in a nod to both Vassar’s brewing roots and the Beer and Bike Society. Despite all the drunken fun of the day, Vassar’s ban on alcohol on campus meant that supporters and cyclists had to congregate just outside the main gate to celebrate. This led another duo to wear light dresses as “Wisdom and Purity,” reportedly to “uphold the [Vassar] seal by confiscating empty beer cans.”

Nonetheless, after the victors were crowned and the triumphant beers were drunk, traditional Vassar and Yale style was restored. A banquet and dance was always held, where students could rejoin their fiancés and dates, listen to acapella music from the Vassar Flora Doras and Yale Whiffenpoofs, and tend to any injuries. The styles showcased at the celebrations reaffirmed Yale and Vassar as two of the most important schools in setting collegiate fashion trends: The men wore their club jackets and Brooks Brothers shirts and ties, while Vassar students donned their own collegiate garb in the form of Fair Isle sweaters, Bermuda shorts, official Vassar College blazers, and plaid skirts.

The race got its most high profile coverage at the 1952 running, when LIFE magazine sent photographers to capture the chaotic scenes, but actually the race continued to run annually until 1954. Unfortunately the extravagances of the race, not to mention the dangers, led the college administrations to step in and cancel the event.

Yet for those few years the event captured a sense of collegiate fun and serves as an excellent lesson in iconic midcentury Ivy and Vassar style. — REBECCA C. TUITE

All images via the LIFE Magazine archives.

13 Comments on "The Yale-Vassar Bike Race"

  1. Wow, great article.

  2. Wonderful. Would that such a splendid tradition were not killed off.

    Of course, I imagine that modern participants would wear nothing more than jock straps and have to snort a line of meth at the change-overs, so perhaps it’s just as well.

  3. A fascinating bit of collegiate tradition. Besides the immense entertainment in reading this blog on a regular basis, the historical edification is an equal perq.

  4. Really interesting article! One note to the editors: if you’re writing to a primarily American audience (which I’m not sure you are, here…but you did spell “humor” the U.S. way), be aware for most U.S. readers “fancy dress” means “evening clothes” (worn without irony), not “masquerade costume.” A small difference, but potentially confusing.

  5. Fantastic stuff,. Please keep it up.

  6. Interestingly, there was a brief period when the schools’ administrations considered overcoming their spacial distance by a different means:

  7. That’s true, and the book “Full steam ahead in Poughkeepsie: The story of coeducation at Vassar, 1966-1974” by Vassar Historian Elizabeth Daniels covers this well from Vassar’s perspective.

  8. Re-institute the race elis! A harvard guy dares ya!

  9. Charlottesville | March 12, 2020 at 10:43 am |

    Thanks for re-posting this. What a great article.

  10. Old School Tie | March 12, 2020 at 11:34 am |

    And a great comment from Henry.

  11. Speaking of jockstraps, I was very amused to see what looks like an homage to the Droogs and their codpieces! Or perhaps that’s a couple of decades too soon?

  12. Henry Contestwinner | March 14, 2020 at 5:57 pm |

    Thank you for the compliment, Old School Tie.

  13. Vern Trotter | March 15, 2020 at 9:25 am |

    I believe there is still the World Naked Bike Ride each July from Boston to Cambridge after 9 PM. All male, as far as I know, always attracts a couple dozen riders. One July night, when I still lived at Dartmouth and Newberry streets, I was interrupted in my frequent trek to the old Ritz bar by the group riding totally bare assed turning left on to Newberry from Clarendon. One rider’s chain slipped off and he was left sans any clothing as he tried to fix it to no avail; I continued on to the Ritz where I regaled the regulars with my account of the episode. No idea what eventually happened with the very unhappy lad with the chain problem.

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