2025 Cannonball Reunion
October 11 & 12, 2025 | Cars & Coffee Darien
When Speed Limits Were Suggestions and America Still Had Balls
Join us for the annual gathering of automotive outlaws at the sacred launching grounds of the final Cannonball Baker Sea-to-Shining-Sea Memorial Trophy Dash. This year’s reunion promises to be our most spectacular celebration yet of the magnificent, completely illegal legacy that proved good drivers in good automobiles could traverse America faster than any government bureaucrat ever imagined.
HOTEL ACCOMODATIONS
For those of you coming in from out of town, we have put aside a blocks of rooms at the Stamford Marriott. The Marriot – which was our official hotel for the past two years – is $209/night plus $10 parking for self parking. It’s easy to get to (it’s right off I-95) and has parking for your trailer if you’re bringing a special car. We have 20 rooms at each hotel and they are blocked for the evening of October 12th. Unused rooms will only be held until September 26th – after that they go back into the pool.
EVENT SCHEDULE
Saturday Dinner – 6:00 PM – 10:30 PM Crab Shell Restaurant | Hosted by Jim Clifford and Dick Gildersleeve Celebrating the birthdays of Lady Pamela Yates and Judy Stropus Limited seating | RSVP required
Sunday Cars & Coffee – 7:00 AM – 11:00 AM The main event begins at our hallowed Darien location. Early arrivals welcome—true automotive anarchists have been known to appear the night before.
Featured Attractions:
- Lady Pamela Yates, Stacy, Brock Yates Jr., and others.
- Original Cannonball participants and modern-day runners
- Authentic Cannonball cars including Brock’s original Challenger and Brock’s restomod that Dennis Tretter is working on.
- Dennis “Mad Dog” Menecini’s Chevrolet dualie (pending successful coercion)
- Public unveiling of the infamous “traveling” Cars & Coffee Darien sign
Sunday Farewell Brunch – 11:30 AM – 2:30 PM Rive Bistro, Westport | Seating limited to 50 guests RSVP early—last year sold out faster than a Ferrari Daytona crossing Nevada
DINNER / BRUNCH NOTES:
- You can make your meal selections at the time you purchase your tickets.
- If you are attending with a guest, please use the “+” and “-” buttons below to increase or decrease the number of guests.
- If you are coming for Saturday dinner but not Sunday brunch, please use the “+” and “-” buttons below to set the number of brunch attendees to 0 before you click the get tickets button (and vice versa).
This gathering celebrates more than automotive history—it honors the spirit of American freedom, the courage to challenge authority, and the belief that some roads are meant to be traveled at speeds that would make safety commissioners weep.
Reserve your spot among the automotive faithful. Because some traditions are worth preserving, even when they’re completely illegal.
