Wilson, 86, who lives in Potomac Towers, said she doesn't know what she will do now that the eatery is closed.
"It's friendly and you can have a cup of coffee and nobody bothers you," she said. "It's going to be terrible."
At the Highlander, Patrons could count on being served two eggs, toast and home fries for 99 cents.
"It's close for me and everybody always treated me nice," said Raymond Johnson. "I give the people a hard time every once in a while, but it's all in fun."
Johnson, who has a pair of the establishment's soup bowls from years ago, stopped by Thursday to ask about buying the rest. The restaurant is selling off everything from utensils to milkshake machines.
Manager Rhoda Deter, who has worked at the restaurant for 15 years, said the store was popular with senior citizens in nearby apartment buildings as well as with downtown office workers. Seniors, especially, will be hard hit, she said.
"You see people coming here as long as I can remember. I know a lot by name and they know me. It's always been a friendly place," Deter said. "I really feel sorry for the older people who walk up here."
Deter said some of the six restaurant employees will work in the store, at least for a while. After that, they will be unemployed, she said.
Deter said the restaurant has maintained a loyal base of regulars, but the number of customers has steadily declined over the years.
During the restaurant's heyday, six waitresses were kept busy waiting on customers during peak periods. More recently, however, one or two waitresses could handle the job, Deter said.
A smoking ban passed by the state about 18 months ago accelerated the customer decline, she said.
"When I came here 15 years ago, they used to stand in line to get in here at lunch," Deter said.
Several factors contributed to the decline, Deter said. McCrory's Stores filed for Chapter 11 bankruptcy protection in 1992 and has closed more than 200 stores nationwide.
In addition, there are fewer and fewer stores drawing people to downtown Hagerstown. Paradoxically, Deter said, there are more nearby restaurants competing for the business that remains.
"You might as well hang a crepe on this place, because I think downtown is dead," said one woman, who said she has been eating at the Highlander for about 50 years.
Elwood "Woody" Tingle, 78, who managed the restaurant from 1951 to 1984, recalled the day when a soda cost a nickel, a piece of pie cost 15 cents and a milkshake could be had for a quarter.
The menu has stayed pretty much the same over the years, Deter said, and while prices have gone up, they have remained comparatively low.
The 99-cent breakfast was the biggest draw, Deter said.
"You can't beat that anywhere in town," she said.
Lunch prices were low, too, she said. Daily lunch specials, which included a main dish and a side dish, were $3.89.
For loyal customers, low prices weren't the only consideration. Many regulars said they liked the Highlander because they could chat with old friends and talk to friendly employees.
Deter and Tingle said the restaurant had in the past triumphed over tragedy. It was twice rebuilt after being damaged by fires. The first fire struck in 1945, the year Tingle moved to Hagerstown. The second fire hit in 1975, not long after Deter moved to the area.
That's part of reason that many cannot believe it gone for good, employees said.
Lori Nichols, who has worked at the Highlander on and off for 17 years, said she was still in a bit of shock. Employees only recently learned the restaurant would close, and did not get official word of the date until last Friday.
Nichols said she had no idea what she would do now. "We haven't really thought about it. It all happened so quickly," she said.
Tingle, who lives on Chapelwood Lane, said the restaurant was "nothing to start with" when he started working there in 1951.
Over time, it grew and became "one of the better restaurants in Hagerstown," he said.
Tingle said he exerted extra effort to keep his customers happy. During heavy snows, for instance, he fought his way through the snow while most other businesses were shut down.
"I'd open up the restaurant for about four hours to feed the people," he said. "That was my duty."