"The Smartest Rally In The World."

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 eight most prestigious and gorgeous universities on the planet: First day is the Start in Newport, RI and then on to Brown, Harvard, and Dartmouth (201 miles). Second day is Dartmouth to Cornell (297 miles). Third day is Cornell to U. Penn (230 miles). Fourth day is U.Penn, Princeton, Columbia, Yale, and then back around to the Finish in Newport, RI (272 miles).

Drive Wrecklessly

Just kidding! The Eleventh Old's Cool Tour is scheduled for September 3rd - 6th, 2026, and will be a GTA (Game-Tour-Adventure) event and the annual fundraiser for the Old's Cool Academy. There will be at least one timed stage, a hillclimb at Mt. Equinox, and/or an SCCA autocross. The only specific Old's Cool Rule is that the automobile must be at least as old as your graduation year, or pre-2001 if you didn't finish before then.

Keep in mind this is not in any way, shape or form a "race" – obey speed limits and all local laws – the whole point is just to have fun. No diploma required. Originality and creativity encouraged. Life's short.

We guarantee you'll have a blast meeting up with classmates and fellow aficionados, talking shop, enjoying incredible amenities, and raising money, dust and Cain for a great cause.

How much does it cost?

Unforgettably charming and authentic road trip with a posse of interesting fellow enthusiasts on the most beautiful roads in this perfect part of the world? Priceless. Poetry and Visa commercial satire aside, the entry fee is $5000 (per team, double occupancy). You can also sponsor one of our rally cars for $1,000, $500, or $100.

Day-Tripper's Special

Got a good reason for taking the easy way out? Since a 4-day, 1,000 mile voyage is a big commitment, we're offering an “Day-Tripper's Special – we’ll start at 7:22 am in Newport, with our first stop at Brown, and then lunch at The Harvard Club around noon. You and your lunch mates can then head home, while we continue on our way up to Dartmouth for the night. This Day-Tripper's Special is $100, and includes lunch.

Ready to donate?

If you'd like to sponsor a car, or just want to make a contribution to this fabulous fundraising and hellraising! adventure around New England's eight finest institutions of higher learning (nine if you count us!) you can do so here.

Reach out anytime!

Questions? Or just want to say hello – don't hesitate to ring Timothy Cataldo up on (401) 572-7090, or email: timothycataldo@oldscoolacademy.com. Or just stop by the Academy anytime — 38 Charles Street, Newport, RI 02840 – door's always open.