Are you ready to go back to school?

The assignment is easy: have fun driving your vintage automobile 1,000 miles through scenic New England, New Jersey, and Pennsylvania visiting en route each of the 8 most prestigious and gorgeous universities on the planet. You'll have a blast meeting up with classmates and fellow aficionados, talking shop, enjoying incredible amenities, savoring great foo… wait a sec, the point is not to have fun, it's to win the rally, of course. Not only win, but totally beat everyone else. And owning the rarest and most expensive machine wouldn't hurt either. All the while being fake self-deprecating and charming. Haven't you learned anything at all since the day you graduated?

"Unglaublich super geil fun."

Seriously, was the Fourth Annual 'Rally Around The Ivy League 2018' a success? Um, hell yah. For us, anyway: we went out there and conquered our fears, the road and the communists, and had an absolute blast! Mille Miglia, Schmille Schmiglia. Just kidding, about the communists, I mean.

The Fifth Annual Old's Cool Tour is scheduled for September 5th – 8th, 2019, and will be a GTA (Game-Tour-Adventure) event, with the emphasis on adventure, and fun. There will also be at least one timed stage, a hillclimb, and an autocross. The only specific Old's Cool Rule is that the automobile must be at least as old as your graduation year, or pre-1993 if you didn't get diploma'ed before then. Keep in mind this is not in any way, shape or form a "race" – obey speed limits and all local laws – and the whole point is just to have fun. No diploma required. Originality and creativity encouraged. Life's short.

Unforgettably charming and authentic road trip with a posse of interesting fellow enthusiasts on the most beautiful roads in this part of the world? Priceless. Poetry and Visa commercial satire aside, the regular entry fee is $4999 (per team, double occupancy), and the closing date for all entries is March 1, 2019.

For more details, check out the MASTER PLAN for 2019. >

Come aboard!

Unfortunately, or fortunately, ours is not a kumbaya world, where everyone gets invited to the party, or receives a participation trophy for losing. The Old's Cool Tour is kind of by invitation only, so please call Johnny Mustard at 203.451.5127 to reserve your spot as soon as possible. You don't have to be an Ivy League grad to enter, but they will get preference; then one-of-a-kind gorgeous cars, then celebrities. Not. Celebrities are first on the list: automatic yesses for Amanda Peet, Natalie Portman, Emma Watson, and Elizabeth Banks. No hot rod yahoos or Sunday drivers, please.

"Live the dream."

Got into a minor scrape, literally.

I love driving old cars, preferably without synchromesh, and I always wanted to experience the Mille Miglia in Italy at least once in my life. Sigh, it's just not possible, logistically, financially, or emotionally at this stage in the game. I researched road rallies in here in the States, and endless straight, flat highways in Texas just don't appeal to me. So I came up with my own quixotic idea that I thought just might be crazy enough to fly: The Old's Cool Tour – Rally Around The Ivy League.

Meantime, stand up straighter.


'Old's Cool' kind of sums up our philosophy in a neat little turn of phrase. Kind of, because our actual motto is – "Shamalamadingdong the doo dang dee", but that's another story. No lie, look what we have here: Common sense. Nerve. Backbone. Self-reliance. Perseverance. With a shot of wry, served neat. So why not flaunt your charming lack of political correctness with wit and style, and a little grit to boot? And yes, we know that's a Triumph motorcycle in the photo, but who says a few hell-bent-for-leather wrist-twisters with the right je ne sais quoi aren't going to be welcome in our rally?


Mustache man Jim sporting the short-sleeve Old's Cool flannel-under look on his 1959 Triumph – all iron, sinew, and real.

Are you ready for the big (Ivy) league?

Sign up now and get the latest news, updates and argy-bargy from the cheap seats. We'll only contact you when it's totally worth your while, and promise not to spam you to death with irrelevant crap. Ever.

Eager to get in touch with us? We can also be reached on 203.451.5127, or OCT Global HQ is located at 13 Wilson Road, Weston, Connecticut 06883 if you'd like to pop in – door's always open.

Old's Cool = Old School + Wit™