While some herald September’s quieter streets and diminishing crowds, Eugene (Geno) Courtney said the end of the season makes him blue.

“It’ll start winding down,” he said Wednesday, sitting on the South Summer street bench that doubles as his front office. “Come Labor Day, with the sudden drop, I get a little sad, a little bit depressed. I haven’t gotten used to it. I enjoy the people being here. I enjoy seeing the people.”

From the bench, Mr. Courtney, 73, can see some of the fruits of his last 50 summers on the Vineyard: Shirt Tales T-shirt store, diagonally across the way. Directly behind is Scoops ice cream, where Mr. Courtney gets a scoop or two of maple nut and coconut every day, “to check the consistency.” Across Main street is The Port Hunter, a new restaurant run by Mr. Courtney’s sons, Ted and Patrick.

The South Boston native who became one of the Vineyard’s most successful businessmen said this week that he’s retiring, and leaving the businesses in the hands of his sons.

He’ll have time to spend with Whitey B., a 12-week-old yellow Labrador named after an infamous fellow Southie resident. (Whitey the dog actually hails from Mississippi. “I’m waiting to see if his bark has a drawl,” Mr. Courtney deadpanned.)

He said he plans to travel. “See Rome,” he said. “Go back to Spain.”

“I probably won’t be on the bench as much as I used to,” he added.

Mr. Courtney grew up with two sisters and a brother in a four-decker in South Boston’s City Point neighborhood. He stopped going to school in sixth grade and first came to the Vineyard in 1962, when he was 22. He worked summers as a barber in Oak Bluffs. In 1970 he moved to the Vineyard full-time, and four years later he moved to Edgartown. He bought Willoughby’s paper store on Main street and worked there while bartending at the Edgartown Yacht Club, working at the Seafood Shanty, and still cutting hair.

“I was young and hungry,” Mr. Courtney recalled, wearing a gray sweatshirt emblazoned with “Vineyard” in red. That schedule lasted for about a year, as the paper store business started to develop and the other jobs fell away.

Now, he said, gesturing every which way, there are eight businesses in Edgartown. In 1995 he bought the historic building at the corner of Main and North water streets that houses the corner paper store today. He succeeded in opening a movie theatre right on Main Street, and he also owns seven condominiums in that building. There’s a Shirt Tales shop in Vineyard Haven and a couple of buildings he owns that other people use. He said he collected the buildings as they became available, a lot of them self-used as businesses.

For Mr. Courtney, there’s “something about the Vineyard,” he said, as Whitey B. gnawed on his hand. “I liked it, I was able to make good money here. A lot of opportunity here.”

But, he added, “I don’t know how many people can come here and own 40 per cent of Edgartown.”

Owning businesses in different towns could be hard to manage, he said, but in Edgartown, he can just go from building to building. “Sitting on the bench, I can see if something’s not right, you know.”

His business partner is his wife, Barbara — the two are still married but no longer together. She does office work for the business while their sons have started to work on everything else. “Probably another year or so, she’ll be ready to give ‘em a shot at running it all, you know,” he said. The couple have a daughter, Lauren, who works in fashion in New York city.

Over half a century, “I’d say the whole Island [has changed],” he said. When he first came and was a barber, he would go to work on Labor Day, give half a dozen people a cut, and the shop would close at one. “At that time in 1962 I could look out the door and you wouldn’t see a person on the street until the next Memorial Day,” he said. “No fall season, no tour buses in the fall. No shoulder season. It was deadsville.

“Then gradually it came back and Edgartown seems to be a good mix of shops now. In our development of these properties, there are certain things we know the town needs.” With one downtown liquor store moving to the airport, Barbara Courtney recently opened Port Supply Company near the movie theatre.

The key is “trying to decide what is going to be a good mix,” Mr. Courtney said. “You gotta make the town work.”

Now Mr. Courtney is watching as his sons take the reins. All of his children grew up working in the family business as soon as they could. This was back in the day when the paper store was the biggest seller of Sunday papers. “If papers were late because they [airplanes] couldn’t fly, [customers] would go berserk,” he said, and those who “couldn’t get the Wall Street Journal to see stocks and bonds would come in and give the clerks a hard time.”

His children went to school in Florida during the year and worked summers on the Island. “The boys kind of grew up in the business,” he said. “They are doing okay. They don’t need me around . . . they’re doing all right on their own. I can kick back a bit.”

He added: “I know more than them but they know more than me. So they’ve kinda come into their own.”

The boys go to trade shows — Mr. Courtney said he hasn’t been to a show in 10 years — and have taken over the remodeling and repair work that used to fill Mr. Courtney’s winters. They opened Backwater Trading Company on lower Main street several years ago.

The Port Hunter restaurant has “been very successful,” Mr. Courtney said. “Personally I wouldn’t be in the restaurant business. But they’re young so they can do it and learn.”

The Vineyard where his sons live and work has changed for the better over the years, he said. He’s observed South Boston change, too. He goes through the neighborhood every time he visits Boston, where he has a home. “It’s hard to find a triple decker that hasn’t been condoed,” he said.

Southie was different when he was growing up. “The streets were our playground. Every night, every family would sit on the front steps,” he said. “Now properties are kept up nice. You don’t see people sitting out there like they used to in the old days.”

But Mr. Courtney has traded the porch in South Boston for the bench in Edgartown, where even on a busy summer day there is small-town neighborliness. Someone stopped in their car to greet Mr. Courtney, and he had stopped for a chat with one of his sons. Leaving Whitey on the bench, Mr. Courtney crossed the street to talk to realtor Tom Wallace. Dukes County superior court clerk Joseph E. Sollitto Jr. walked down from the courthouse for a break and a scoop of caramel chocolate chip. Several people stopped to admire Whitey.

“His real name is chick magnet,” Mr. Sollitto chimed in.

With a puppy to keep him on his toes and his sons taking over, “I suppose I can say I’m retired but I’ll probably still answer questions for them,” Mr. Courtney said. And he can still take the pulse of the town from what people refer to as Geno’s bench.

“You see a lot. People-watching is quite educational,” he said. “You really don’t need an office when you have a bench.”