The Boston Cup is billed as one of the “top five classic car shows in the US,” and has become a fixture in the Northeast scene over the years. This year marked its 15th anniversary, and vintage car connoisseur and event correspondent-at-large Bill_Noon sent us this brief report of the October event, which includes his own photos covering the breadth of this year’s show. Enjoy!
Boston Common—Boston, Massachusetts, October 12, 2026
For more than a decade, Richard Doucette, the founder of the Boston Cup classic car show, has invited me to join the festivities on the Boston Common each October.
I initially declined because of my busy summer schedule and the fact that I lived in Southern California. After relocating to an old farm on the New Hampshire seacoast, I ran out of excuses and decided to attend for the first time in 2024.
I returned last year, and this year, I was terribly disappointed that the show had to be postponed because of a powerful (and early!) Nor’easter that dumped an insane amount of rain all over New England.
Fortunately, Richard and his team rescheduled it for October. The weather was postcard-perfect, and the event was well attended by some truly world-class classic and collectible automobiles.
The number of Bring a Trailer alumni vehicles was astounding. I recalled more than 15 just from memory, and I am sure there were more.
Each year, the event kicks off with quite a party in the evening, followed by the show the next morning. The host hotel for those traveling was the Revere Hotel near the Boston Common. Not only did the entrants receive a hefty room discount, but the enclosed on-site parking—ever-so-conveniently close to the event—was a huge plus.
This year’s Best of Show went to a fantastic 1965 Ferrari 275 GTB owned by Joey Kaempfer.
The Chairman’s Award went to an instantly recognizable 2003 Ferrari Enzo owned by Barry Lundgren.
Images: The Boston Cup
First Place in the American, German, and British categories went to a 1963 Lincoln Continental Sedan owned by Jack Child, a 1972 Porsche 911S Targa owned by Peter Tedeschi, and a jaw-dropping 1915 Rolls-Royce Silver Ghost owned by Billi Carey, respectively.
Image: The Boston Cup
There was even an award for Mustangs! First Place went to a 1965 Ford Mustang fastback, which was probably the finest restored example I have ever encountered, owned by Paul Breault.
First Place in the “Other” category went to a 2007 Spyker C8 Laviolette owned by Ray Di.
Image: The Boston Cup
A McLaren 570S owned by Haytham Taktak received First Place in the Supercar category.
Last but not least, my friend and I took First Place in the Italian category with our 1957 Fiat 1100/E 103 Berlina, which proves that even four-door sedans can win in a field full of Italian classics and exotics!
Check out the event website for more information and the full list of this year’s winners.