Gentlemen, Start Your Engines: Rally Around The Ivy League 2017


Want to take a unique motoring vacation through the Northeast next month? There’s still a chance to register for the Rally Around The Ivy League tour. “The window of opportunity is still open a crack,” says organizer Timothy Cataldo. “Call immediately on 203.451.5127 or email to reserve your spot now!” Below is Cataldo’s description of the event, which we first posted last December.

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Everyone knows “The Official Preppy Handbook,” which first came out when I was in high school, and I still have my copy right here on the desk as I type this. The wisdom and cheek of this pink and green bible still makes me smile and shake my head, even after all these years, in wonder and admiration. So I’ll begin this quixotic adventure there:

Officially the Ivy League is nothing more than an athletic conference, comprising eight colleges….These schools are not entirely the oldest, the best – or even ivy-covered. But in the public imagination, they are something very special.

Before the term “Preppy” was popular, “Ivy League” was used to describe a certain kind of person…He was smart, rich, well-educated – or at least he presented himself that way. The Ivy League schools became the mythic focus of the American notion of the young elite.

[But] what’s the point of going to the Right Places if you don’t travel in the right style? Drive off the ferry on Nantucket in a Firebird Trans-Am and you’re really nowhere at all.

The car is as much a key part of Prep paraphernalia as a club tie or the ubiquitous duck. If, that is, it’s the Right Car – the Proper Make, in an Accepted Color, Appropriately Adorned.”

Recently I watched “Love Story” with my son, and even though it’s dated, it’s still pretty witty and charming. And talk about the right cars: Oliver’s 1945-sh MG TC Midget – I love the fact that he and Ali McGraw drive it without the top, summer or winter. His dad (played by Ray Milland) drives a 1969 Jaguar XK-E 4.2 Roadster, in “greensand” with a black convertible top. The license plate is “OB 3” for Oliver Barrett III – a very nice touch – some people can’t get enough of monogramming.

“The Great Gatsby” is and always will be my favorite book, and the thrill that Fitzgerald’s writing gave me when I first opened up my mind to his mellifluous prose, after thoroughly hating Hemingway, is always remembered fondly and with awe. Yes, we could go on and on about Gatsby’s shirts and shoes, and Daisy’s dreamy dresses, but I’m more interested in the car, as people have imagined it, since Fitzgerald was uncharacteristically vague on make and model.

“On weekends,” he writes, “his Rolls-Royce became an omnibus, bearing parties to and from the city between nine in the morning and long past midnight.” The RR was most probably a 1922 Silver Ghost.

It’s a bit curious, then, that Robert Redford drives a 1928 Rolls-Royce Phantom for a story set in 1922; and Leonardo DiCaprio drives a 1929 Duesenberg Model J in the recent adaptation. Nitpicks aside, these are gorgeous monsters that represent and incarnate Fitzgerald’s muscular sense of privilege and masculine love/longing of the automobile in general, and Princeton in particular.

Chris Miller, one of the writers of “Animal House,” was a Dartmouth grad, so we’re going to include the 1964 Lincoln Continental that Flounder borrows from his brother and that eventually becomes the Death Mobile on our list of Ivy League rides. This one has personal meaning to me since we had the same car (in Ivory) when I was growing up, generously given to my mother by her parents – it was the most luxurious thing I had ever seen. In my mind’s eye it’s still the standard for exquisite. Otter’s 1959 two-tone Corvette Convertible C1 is exactly the kind of car a frat-boy lothario would drive. Greg Marmalade’s 1960 MGA 1600 Roadster was the best selling MG of all time – over 100,000 of this model were manufactured – and perfect for an unoriginal twerp like him.

You don’t get more Ivy League than Anton Myrer: Boston Latin; Philips Exeter Academy; Harvard, and then a U.S. Marine serving honorably in WWII. His wistful book “The Last Convertible” made a great impact on me in my younger and more vulnerable years. It’s a charming and nostalgic character-driven snapshot in time. The eponymous automobile was a green, 1939 Packard convertible, nicknamed The Empress, a metaphor for carefree youth, lost forever once war broke out. And man, the guy can write. The story kind of reminds me of a couplet from Dylan Thomas: “Time held me green and dying/though I sang in my chains like the sea.” Unfortunately, his is a world we are losing or have already lost.

Fast forward back to today: I’m not an Ivy Leaguer, or a preppy, and I definitely don’t have the right anything. I’m a college dropout, drive the wrong car in the wrong color, inappropriately adorned: a laughably underpowered and bashed-up 5-speed Fiat that dates back to a time when Brezhnev was still running the world scared. Sartorially, I dress kind of like an unshaven, tone-deaf Keith Richards, and that’s on a good day. But we all have dreams, don’t we?

I always wanted to experience the Mille Miglia in Italy at least once in my life, but it’s just not possible, logistically, financially, or emotionally at this stage in the game. I researched road tours in here in the States, and 1,000 miles in Texas just didn’t appeal to me. So I came up with my own preppy romantic adventure that I thought just might be authentic and original enough to fly: The Old’s Cool Tour – Rally Around The Ivy League.

The assignment is easy: have fun whacking your vintage automobile (at least as old as your graduation year, or 25 years minimum) 1,000 miles through scenic New England, New Jersey, and Pennsylvania, visiting en route each of the eight most prestigious and gorgeous universities on the planet. Do so with friends, lovers, classmates, or fellow car aficionados.

If you’re interested in coming along on this ludic and lovely journey, please visit us at or drop me a line: — TIMOTHY CATALDO

18 Comments on "Gentlemen, Start Your Engines: Rally Around The Ivy League 2017"

  1. Interesting idea. My preference for cars above would be the Healey 3000… beautiful! Might trade the dogs for a Palm Beach Champagne sipping blonde though…

  2. I would love to participate in this adventure. However, at this point it is, as said, not possible logistically or financially. Emotionally, I could do it. I do have a car that would qualify – a ’75 XJ12C, BRG/Bisquit. In typical Jaguar fashion, though, it hasn’t run in years. And likely won’t for several more. I’ll have to read about the tour after the fact. Cheers to all that will be able to go!

  3. @PhilipM

    I also would love to participate in this event, but not possible. Some years ago, I inquired about a 74 (?) Jaguar XJ12, with dual or triple carbs, I believe. The car, according to its owner, was in excellent condition, but had not run in many years. I believe the fellow wanted somewhere around $2K. The deal breaker to me was that the car could not be driven. I could not buy a car that needed to be towed home.

    I settled on a plebian gold color 85 LeBaron convertible, in super nice condition, with a pedigree from Ft. Myers, FL. I like to think that if Gatsby went slumming, it would be in such a car. I can imagine Redford in his pinstripe suit and Panama hat jaunting about, causing Bruce Dern’s disgust.

    The Tour should be fun, but I think the tow trucks and repair shops will have the most fun.


  4. What a nice idea! The first car I remember was my mother’s white Volvo wagon, many beach trips in that one. My favorite car to ride in and later borrow growing up was my father’s BMW 5 series which had nearly 300,000 miles on it when it finally gave up the ghost. Me, I ride the train…but someday!

  5. Guys, I had a Jaguar XJ12, vintage 1972 I think. The live in boyfriend of my secretary at the time had bought it with blown engine from local Cadilac dealer, put a rebuilt engine in it and then sold it to me – I bought it twice during the year or so I owned it. It was like an old girl friend – when it was good, it was very, VERY good! 100 mph and no shimmy or anything. But when it was bad – which was most of the time – it was really bad. Secretary’s husband had it more during that ownership than I did. Two days and 12 quarts of oil for an oil change. Two gas tanks, each holding the highest octane you could purchase. It got a solid 10 or so mpg if a lot of downhill with a good tail wind and a/c off.

    But I will never own or operate a more beautiful or marvelous vehicle. Real wood on the dash and steering wheel. And the first car that my oldest daughter’s car seat ever got clipped into. No wonder she is stil so high maintenance.

    Great article and great to remember those times – I still lust after old AH 3000s when I see them around.

    And thanks for your great website.


  6. In the 1960s, the automobile of choice among trads and hippies alike, was the VW Beetle.

  7. The Man Who Was Thursday | December 16, 2016 at 11:02 am |

    Always loved my Dad’s ’69 AMX in Big Bad Orange color. Sadly it’s been sitting in pieces for te ladt thirty years!

  8. We all agree that the most preppy car of all time is the BMW E30-generation convertible? Honorable mention to a Range Rover of any year.

  9. The Man Who Was Thursday
    ’69 AMX, your Dad is bad ass.

  10. Atlanta Pete | December 16, 2016 at 5:09 pm |

    I owned a willow green 1970 XKE for about a year and a half until speeding tickets and the reality that my 6’4″ frame didn’t fit very well when the top was up caused me to part with it. I owned it when I met my wife who later said she went out with me despite the XKE. Next was a 1972 MB 280SL and a 1972 MB 280SE convertible until the first child arrived and I made the difficult choice of replacing the SE convertible with a Volvo. I kept the 280 SL for 20 years and when I finally sold it for more than twice what I paid for it, which I now regret, I bought a 1967 AH Mark III. It was hot in the summer and cold in the winter, but terrific for about two months in the spring and two months in the fall. The problem was that my wife refused to let the children ride in the “death trap.” despite their pleas to ride in “Daddy’s the death car.” Alas, I’m now driving practical Japanese vehicles that are very reliable, comfortable, and utterly boring.

  11. @ Atlanta Pete

    For the last couple years, I’ve been lusting over Jaguar XK8’s. Relatively cheap, I fear if I actually looked at one, I’d impulsively buy it. On a Craig’s List ad, there’s a nice one, a 98 or so, for $3,800 for sale, been for sale for best part of a year. I’m sure that $3,800 would be a drop in the bucket, so I’ve resisted the urge to look at it. I’ve read that the required timing belt job costs $3K, otherwise, a destroyed engine is the result of this neglected maintenance. Owning such a car would cause immeasurable grief, I’m sure/

    The missus has been leasing Rav4’s for five years now. As you say, very reliable, comfortable, and utterly boring. Those Rav’s make my 80 HP underpowered LeBaron seem positively exciting.

  12. Proud owner of a red Volvo 240 Grand Luxe here…in fact every member of my family drives a Volvo 240.

  13. I wish I had kept the Saab 900s that I owned in the late 1980s….a wonderful car and fairly ubiquitous on new england college campuses back in the day.

  14. Is the Honda Element preppy?

  15. Orange Fiji | August 15, 2017 at 10:08 pm |

    RIP Flounder. Taken from us much too soon.

  16. I drove a ’61 Morris Minor for my last two years at Cornell.
    Not a great car for Ithaca winters- Lucas electricals !!. Being
    pragmatic and living off campus, I must have been the youngest
    person in the Southern Tier who taught himself to use the
    auxiliary crank supplied by the manufacturer. Eventually,
    I blew up the engine driving at top speed( around 60) in
    regular commutes to visit my future ( and current) wife
    at Bryn Mawr over two hundred miles away.

  17. @Michael I had to replace my SAAB 900 hatchback last year as rust was gaining the upper hand. I was lucky enough last year to buy to buy a 1992 900 Turbo convertible with 51,000 on the clock that had spent its life in the underground garage of a Mayfair mansion block. Not so practical as the hatch but I run it hood down summer and winter.

  18. elder prep | April 27, 2020 at 2:26 pm |

    I am, again, a little late for this thread. My gift to myself on departing the U.S. Army was a canary yellow Triumph TR-6, right off the boat in Baltimore harbor. It was really my mechanical mistress as it required as much tender loving maintenance. The sound of its tuned exhausts and the top down with my stunning blond girlfriend (now Mrs. of 48 years) was heady. However, marriage, outrageous insurance, oh did I mention maintenance? parted with me in 1972. I still lust for another one. . . .

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