Labor Day weekend: Classic cars roll into Southold, Greenport comes alive
From strolling through Greenport to taking in the sights at the Southold Boy Scouts’ 36th annual antique car show, Labor Day weekend brought people across the North Fork together to enjoy the last unofficial days of summer.
Claudio’s Marina was packed like sardines, as Greenport celebrated the end of the summer in one of the North Fork’s hottest locations.
Jeremy Geller and Josh Dugan took their families into Greenport for the holiday weekend, taking in everything it has to offer. They’re not Greenport residents, but they’re no stranger to the hamlet.
“The people, the scenery, the weather,” are all reasons why Mr. Geller and Mr. Dugan came out east, Mr. Geller said. “Saylor is new, but we’re big Claudio’s fans.”
It’s not just the party scenes that attract attendees to the Village — the carousel was a hit for their children and he said the kids had a “great time.”
As Labor Day weekend brought visitors and locals out to enjoy the North Fork, more than 100 classic and modern cars rolled into Southold on Saturday for the 36th annual Boy Scouts Troop 6 antique car show, continuing a longtime tradition.
All of the money raised from the event funds all trips, merit badges, the annual Scout camp in Connecticut, local camping, ferry costs and other scout activities.
Of the roughly 120 cars in attendance, 75 of them received a trophy, as they’re judged and graded by nine judges on four different categories, which all have sub-categories; Exterior, Interior, Engine and Chassis and Miscellaneous. It’s not subjective, as every car needs to have specific items like the correct wiring, hoses, glass and more. The grading system is out of 100, with additional awards going to the top three modified cars and top three stock cars based on the scouts’ choice.
“I think this is the most that we’ve had probably in the last couple of years that we’ve been doing it,” said Boy Scout Troop 6 committee chair Jennie Boyle. “I think it’s a good showing. We got a lot of different cars this year, newer cars, a lot of older cars and a lot of clubs reached out to us.”
With the population down on the North Fork and enrollment down in the schools, Ms. Boyle said she’s worried about this being the last car show.
“We don’t really have any cub scouts coming up right now,” Ms. Boyle continued. “We do have some boys that will still be in the troop, but because of the low classes, it’s definitely a concern. We have a lot of eagles graduating this year.”
For Gary Steinfeld, whose two sons graduated from Southold High School each of the last two years are off at college, but, Mr. Steinfeld still attends the show with his 2023 Dodge Challenger. Jake Steinfeld, the oldest son, attends Cornell University and studies at the Dyson School of Business, while Nate Steinfeld, the 2025-2026 salutatorian, went down to Nashville to attend Vanderbilt University, interested in filmmaking and the entertainment industry. He’s even going to try stand-up comedy, as well — ironically due to his comedy-led salutatorian speech at the high school graduation. Jake was also the salutatorian of his class.
“We come every year and I brought it here today to support the troop,” Mr. Steinfeld said. “It’s a tribute car to the 1970 Challenger TA. They wanted Dodge to race the Challenger in the Trans AM series, so they had to make production cars in order to get into that certain amount of production cars.”
The show attracted people from up-island as well. Shaun Fleischer, a Holbrook resident brought his 1972 Chevrolet Chevelle. His parents live out in Mattituck, so he decided to bring his orange, original color vintage automobile to the show.
“I just love car shows, if I did win, it’d be a bonus,” Mr. Fleischer said.
He referenced an orange Plymouth Road Runner, which was at the show across the field at the Peconic Community Center, as one of the next cars he wants in his collection. The ’72 Chevelle was his first car, but would be interested in adding a 1970 Chevrolet Chevelle or even a Superbird in the future.
All photos by Nick Mongiovi
