Ron Caffrey, who started working full-time for the Riverhead Highway Department in 1981, on his last day of work, March 30, 2022. Photo: Denise Civiletti

One of Riverhead Town’s longest-serving employees retired yesterday after 41 years on the job.

Highway Labor Crew Leader Ron Caffrey worked his last day on a job he says he loved to the end.

Caffrey, 67, a Riverhead native and lifelong resident, started working full-time at the highway department in August 1981, after working part-time jobs in the department for a couple years before that.

The son of a vegetable farmer who at one point owned some 400 acres off Middle Road, Caffrey worked with is father on the family farm growing potatoes, cauliflower, cabbage, turnips and other vegetables. When he and his first wife learned they were expecting a child, Caffrey said he decided he needed a job with benefits, so he went to the highway department on Osborn Avenue and asked then-Superintendent Frank Lescenski if they’d be hiring. The answer was basically, “When can you start?” And the rest is history.

He sat in the same small superintendent’s office at the “highway barn” Wednesday to look back on his four-decade-long career. Over that time, Caffrey served under seven highway superintendents, beginning with part-time work under longtime Superintendent Alex Horton in 1979 and ending with the current, newly elected Superintendent Mike Zaleski, a fellow longtime highway department employee.

The 1973 Riverhead High School graduate said he’s done just about every job at the highway department other than superintendent — and at one point he considered running for that post, an elective office. He served as deputy superintendent for eight years under Superintendent Mark Kwasna, a former town councilman. His dedication, hard work and positive attitude led to the town’s labor-management committee naming Caffrey Employee of the Year for 2001.

Riverhead Highway Department Crew Leader Ron Caffrey at the Osborn Avenue garage Wednesday afternoon, sharing stories and laughs with co-workers at a coffee-and-cake sendoff on his last day of work. Photo: Denise Civiletti

Caffrey said he’s seen a lot of changes in the town and in the highway department over the years.

When he started as a laborer, the department didn’t have the equipment it has now. “You did a lot of everything by hand, picking up papers, loading leaves into a pay-loader with pitch forks,” he recalled.

“We had one chipper. You threw the branch in and you ran because it got to a certain point it would shoot back out at you. They called it a chuck and duck,” he laughed.

Highway workers today, “take their life in their hands” in other ways, Caffrey said. Drivers are “constantly on the phone…and highway guys, state county or town — you’re a hindrance to people when you’re doing your job. You’re in their way. It’s gotten really bad since they invented the cell phone,” he said.

The biggest change in the highway worker’s job, though, has been the development the town has experienced over the past four decades — resulting in many more roads to plow.

“The amount of housing developments. It’s unbelievable,” he said. When he first started, he said, he plowed from Roanoke Avenue east to Herricks Lane. “And there was maybe four housing developments. That’s all you had. And now? It’s unbelievable.”

Ron Caffrey with the vintage 1950s-era Walter plow truck, which he said was his favorite. Photo: Denise Civiletti

Caffrey said in his career at the highway department he’s done every single job there is to do, “soup to nuts,” except line striping — which used to be accomplished by a man riding alone on a small buggy-like vehicle painting lines on the pavement. He was followed by a truck with a man riding on a seat off the back bumper putting down traffic cones. (Zaleski recalled at one point he did that job himself, riding on the seat off the back bumper “with the exhaust pipe in front of you.”)

Caffrey’s favorite job of all was snow-plowing.

“Just being out there” in the snow, on isolated roads, all through the night, fighting to keep them open, he said. “Sometimes you go out and you’ll be going and going, going for hours — and you look behind you and it’s like you did absolutely nothing,” Caffrey said. “People don’t realize what it’s like. They they should go out with these guys one time and just see what they go through,” he said.

The people who venture out in the middle of a snowstorm and invariably get stuck in a drift really impede the plow truck driver’s work, Caffrey said. “So you wind up pulling the guy and you pull them out and then down the road, you’re going down the road and then 10 minutes later, there he is, he’s stuck again. And once you stop, that’s it. You’re all done,” he said. Plow trucks get stuck too.

Hurricanes present the toughest challenges, Caffrey said, even more than blizzards. “You really got to keep your eyes open all around you because you never know what’s going to happen,” he said.

“We’ve been out in every hurricane there was,” he said — 1985’s Hurricane Gloria was the worst. Highway crews goes out to pick up limbs and clear fallen trees from the roads, even at the peak of a storm, to make sure emergency vehicles can pass.

He recalled, too, being out for more than 12 hours in a bulldozer pulling disabled brush trucks out of the woods as a wildfire raged in Calverton in the early 90s. In between, he was cutting fire break trails in the woods. Then-Superintendent Charles Bloss road with him the entire time, sitting on a toolbox.

Caffrey said he’s enjoyed pretty much everything about his job, though some aspects of it are admittedly less than pleasant, such as removing dead animals from the road. He estimates that over the years he’s picked up over 1,000 dead deer that were hit by cars. Dead animals are buried by the highway department at a designated site over on Youngs Avenue, Zaleski noted.

“One time, even a cow,” Caffrey said. Zaleski was incredulous.

“A cow got out from a farm down in Jamesport, ran down the road and onto the Main Road and got hit,” Caffrey said. He drove a payloader out to Jamesport at 2 a.m. to pick up the cow. “That was the big joke,” he recalled. “Everybody said, why didn’t you take him home and cut him up?’”

The superintendent said Caffrey’s knowledge about the highway department and the town in general will be sorely missed.

“He knows where things are that aren’t on that computer,” Zaleski said, pointing to the monitor on his desk. “He knows where water’s flowing, where it ain’t flowing, trouble areas, drains, this, that,” Zaleski said. “That’s 40 years of knowledge. Even every piece of equipment here. Each one has a little trick or gadget or start it this way, it turns more to the right than to the left. You know, Ronnie knows everything. And that you can’t replace,” Zaleski said.

“They just gotta learn,” Caffrey said, smiling.

Zaleski said he’d love Caffrey to stay but “as his friend, he deserves it.”

“It’s time,” Caffrey said. Lately the cold bothers him. “I’m 67 years old,” he said. “The cold just gets in your bones.”

But Caffrey’s not heading south to a warmer climate. “Everything’s here. My whole family’s here,” he said.

Caffrey lives with his wife Jane in a house a few doors down from the one he grew up in. His son and his two grandchildren live nearby. Caffrey said he’s looking forward to spending time with his family and having the opportunity to tackle a long list of things he’s been wanting to do around the house.

Riverhead Highway Department employees at the highway barn Wednesday afternoon where they joined Crew Leader Ron Caffrey to wish him a happy retirement. Photo: Denise Civiletti

At the end of his last day on the job, his coworkers gathered in the garage at the highway department for coffee and cake, to reminisce about times past, share a few laughs and wish Caffrey well.

“We’ve all looked up to Ron and learned from him,” Zaleski said. “He’s done everything here from changing plow blades as part-time help in the ’70s to deputy superintendent under Mark Kwasna. I can’t say enough about his dedication to the town,” he said. “In my 28 years at the highway department, he’s been a coworker and a boss, but he will always be my friend,” Zaleski said. “Thank you, Ron, we appreciate everything you’ve done.”

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Denise is a veteran local reporter, editor, attorney and former Riverhead Town councilwoman. Her work has been recognized with numerous awards, including investigative reporting and writer of the year awards from the N.Y. Press Association. She is a founder, owner and co-publisher of this website.Email Denise.