For fans of classic cars, there’s nothing quite like a Cunningham. These unique vehicles—of which only 36 were ever made—were the creation of Briggs Cunningham, a sportsman and racing enthusiast whose defining passion was to race cars. Briggs lived in Westport in the mid-20th century, in a home on Beachside Avenue with his then-wife, Lucie Bedford Cunningham Warren. (Lucie’s grandfather, Edward T. Bedford, was a co-founder of Standard Oil, the founder of the Westport YMCA, and the namesake of Bedford Middle School.)
So it’s an incredible, though perhaps logical, coincidence that one of the top Cunningham collectors in the country today, Chuck Schoendorf, is also based in Fairfield County. Chuck, a Connecticut native, owns three of those 36 original Cunninghams. “I’m a lifelong hobbyist with cars,” Chuck tells Westport Lifestyle. “As time went on, I started collecting vintage cars.” Cunninghams, in particular, piqued Chuck’s interest because of their unusual history. “Cunningham’s passion was to build race cars, drive them, and compete,” Chuck explains. “In order to qualify to race at Le Mans [a storied annual sports car race in France], he had to make himself into a manufacturer. So that’s what he did.” Learning about Briggs’ exacting craftsmanship (the cars had to be sent to Italy to be finished, then shipped back to the U.S., before heading to France with Briggs’ own team of mechanics to compete) was exhilarating to a lifelong car enthusiast like Chuck. “The whole story is great,” he says.
In the early 1960s, after Briggs had competed in Le Mans a number of times, Lucie and Briggs separated, and Briggs moved to the West Coast. Some of his designs remained in the area, and about 20 years ago, Chuck heard that there was a disassembled Cunningham at a shop near Bridgeport. Already a fan of the cars and the story, he went and bought it. “It was in pieces,” he says. “It took more than four years to get it on the road.” While working on restoring the car, he became connected with a community of Cunningham enthusiasts. At one of their reunions in Florida, he got word that another Cunningham was nearby, this time in New Jersey. “I got there, and that car was in pieces,” Chuck says. So he bought a second disassembled Cunningham. “I brought that one to a friend and race car builder in upstate Connecticut, and he got it on the road within a year.”
“During the course of all this, I would travel to try and visit as many Cunningham cars and owners as I could,” says Chuck. It was on one of his trips to California that he happened upon another Cunningham—also in pieces—which eventually went up for sale. He had that one sent back to Connecticut, and took about two years to restore it and get it road-ready. Now, Chuck says, his collection is complete. “I didn’t even know I would ever have one,” he says. “I never dreamed I would have three.” (In his garage in Norwalk, he's actually the caretaker and driver for a fourth Cunningham, though he doesn’t own it, as well as a painstakingly-reproduced replica of a Cunningham C-4RK that he does own.)
Chuck can often be spotted driving his Cunninghams on the Merritt or 95—for him, these aren’t trophies, but living pieces of history that he quite simply loves driving. “Some people would be afraid to take one of these cars out, but I’ve put them together before, and repairs can be made if necessary. I’ve put tens of thousands of miles on them collectively,” he says. “I’ll be driving one and say to myself I can’t believe I’m driving a Cunningham. They’re just wonderful to use.” Recently, he got to take one of the cars in his collection on a very special drive: to Briggs Cunningham’s former Westport house, the one on Beachside Avenue.
The property, at 92 Beachside, hit the market in late 2025, a fact that Chuck brought up to his longtime friend and fellow car enthusiast Judy Szablak, who happens to be a realtor, on one of their Sunday drives. “She said, ‘Do you want to see it?’ And I said, ‘well, yeah, I would!’” Judy arranged a visit through the listing agent, Cyd Hamer, and late last year Chuck brought one of his Cunninghams to the property. “It was fascinating to see the house,” Chuck says. “It was fantastic to tour the interior of a house I had heard so much about.” (One special detail that stuck with Chuck was the study, which was crafted from the interior of a boat—sailing was another one of Briggs’ passions.)
These special cars have brought years of enjoyment and dozens of friends into Chuck’s life. “There probably isn’t anyone who spends as much time on Cunningham as I do,” Chuck says. “It’s wonderful to go down to the garage or up to my shop and look at them. But when you start the car, put it in gear, and drive it, you just pinch yourself. You can’t believe it’s really happening.”
“I didn’t even know I would ever have one,” he says. “I never dreamed I would have three.”
“Some people would be afraid to take one of these cars out, but I’ve put them together before, and repairs can be made if necessary. I’ve put tens of thousands of miles on them."