Several legacy enterprise owners are retiring, or planning to, after decades of running their shops and eateries. But the decisions didn’t come easily, they say, with many deliberating for years.

Within the past month, three long-standing businesses announced plans to close their doors: Andy’s Cycles’ last day is Nov. 19, then Anderson the Florist on Nov. 30, and Plotkin’s Furniture at the end of its liquidation sale.

Combined, these three shops have served the region for more than 230 years.

And they aren’t the only ones set to shutter soon. Interface, a stereo store in Keene, plans to close after the owner sells the inventory and building.

Nick’s Seafood in Swanzey announced on Facebook that the restaurant is closing for the winter after Nov. 24. Owner George Nikiforakis put the eatery up for sale a year ago but hasn’t gotten any takers yet, and he said he needs a break. He plans to reopen the restaurant in the spring if no one’s bought it yet.

DelRossi’s Trattoria also went on the market a few months ago after three decades in business. Dublin’s Italian eatery will remain open in the meantime, but a buyer could potentially ditch the restaurant.

Last year, the Apothecary in Keene shuttered after 50 years in business, as did the near 30-year stationery shop, Paper & Roses, in Peterborough.

In each case, the proprietors cited a yearning to retire after decades of being their own boss.

“I think it’s just time for our ages,” Nikiforakis, 68, said.

It’s not because they don’t love their job or their customers, he added: “I wish I could do it ‘til I’m 90.”

Decades in business

Nikiforakis took over the seafood restaurant from his father more than 30 years ago, but like many longtime business owners, his adult children aren’t interested in following in his stead.

John Plotkin’s grandfather founded the family business in Athol, Mass., in 1919. The Keene branch opened in 1955 and is now the last remaining Plotkin’s store. He said his children grew up and pursued careers in other industries.

“Retail does take a certain breed to be good at that,” he said.

Katie Anderson, co-owner of Andy’s Cycles and wife of Bruce Anderson, said their four children grew up working at the shop but found their own professional paths, too: two are teachers, one works with computers and another directs a nonprofit organization in Manchester.

“I think they knew Bruce worked seven days a week,” Anderson said. “He never took a vacation except to go hunting, and I don’t think they wanted that.”

Her husband’s father, Elmer (better known as Andy), launched Andy’s Automotive in the 1940s, she said. When Bruce took over, he refocused the business on bicycle sales and repair, renaming it Andy’s Cycles. He bought the land at 165 Winchester St. in 1984 and built his building a year later, according to online property records.

“He’s been at it since he was about 10, and he’s 78,” Katie said.

Phil N. Suter, president and CEO of the Greater Keene Chamber of Commerce, said that’s why people like Bruce Anderson — the “John Plotkins of the world” — deserve retirement, adding that it’s a positive sign that the community can support these stores and restaurants for so long. He said he doesn’t find it alarming that a few businesses are wrapping up after decades of service.

“This kind of movement around, whether it’s for retirement reasons or other reasons, I consider it kind of ‘normal,’ ” he said.

To address the concern of succession, Suter noted that some companies are exploring innovative solutions, such as Dublin-based Yankee Publishing’s recent switch to an employee-owned model. Others have passed the torch to adult children in the family, including W.S. Badger Co. Inc., where daughters Rebecca Hamilton and Emily Schwerin-Whyte were named co-CEOs last year.

“So it is happening that the next generation is taking over in some cases, but it’s not surprising to me that that doesn’t work in all cases,” Suter said.

He also pointed out that new companies are sprouting up to fill in the gaps left by legacy businesses that hang up their hats. Machina Arts launched a bar and restaurant this year, for instance, as did the Keene Fine Craft Gallery opened on Central Square.

“I think that the really good news for our area is there is a tremendous entrepreneurial spirit,” Suter said.

Hard letting go

A common thread in these proprietors’ stories was the difficulty in letting go of their enterprise. They didn’t cite their own pride or a legacy they’ve built, but rather pointed to their loyal customers, many of whom stuck with them through the rise of online retail and chain stores and restaurants coming to Keene.

Plotkin said the first hurdle to making his decision was the effect on his employees, and the second was the thought of leaving his customers.

“It was kind of heart-wrenching, knowing the reputation and the outpouring that I’ve heard from customers now in the past month, how much people really liked us here and appreciated us and are gonna miss us,” he said.

Katie Anderson said she retired from teaching years ago, but because since her husband continued running the bike shop, she got another job and has since retired from that one, too.

“I think this is his biggest problem, is he feels so committed to his customers,” she said.

People who bought their first bikes as kids from Bruce’s store have brought in their children and grandchildren over the years, Katie said. Supporting generations of families establishes a strong connection.

“And to make up for that kind of loss for the community, we have a barn at our home, and he’s converted the downstairs into a repair shop,” she said. “… So he still can’t let go of that commitment to his customers.”

Katie commended all small business owners for their hard work and lifelong dedication.

At Anderson the Florist, owner Eric Anderson, 83, (no relation to the bike shop) also took over a family business, which his mother acquired in the 1940s from a man who enlisted in the Army. He never planned to be a florist but worked at the shop growing up and, after leaving the military in the late ’50s and graduating from Boston University, decided it was a more stable job.

“I do love it, and my mother taught me — actually both parents taught me what they knew about the flower business and life and growing,” Eric said.

After something like 60 years, he said he’s been thinking about retirement for the past decade but kept putting it off. He’s also struggled with the idea of leaving his customers. Nodding to a cabinet full of awards and accolades, Eric Anderson credited his customers for the success, not himself, because they do the buying.

Sitting at a table in his floral shop one evening, Eric Anderson encapsulated the inner battle longtime business owners seem to face between their desire to spend more time with family and their devotion to the community they’ve served. He spoke slowly and deliberately when trying to articulate his feelings about leaving his life’s work behind, pausing often.

“It feels like I wonder what the future is gonna be like,” he finally said. “I’m gonna live another 10 years, probably. What’s it like? I don’t know; I’ve never done it before.”

Sierra Hubbard can be reached at 355-8546 or at Follow her on Twitter @SierraHubbardKS.