Peggy Bailey has been serving burgers and crab cakes to Catonsville residents since Jimmy Carter was president.

With her Southern drawl and rich laugh,“Miss Peggy” is a beloved fixture at Jennings Cafe, chitchatting with patrons, topping off their coffee and never, ever writing down an order.

“She’s an icon of Catonsville,” said Don Mohler, a former Baltimore County executive and lifelong Catonsville resident. “No one is more a part of the fabric of this community than Miss Peggy. It’s like she’s part of everyone’s family.”

Peggy Bailey  has been waiting tables in Catonsville since 1967. She will retire soon from Jennings Cafe, where she is pictured here sitting in "Peggy's Parlor", a sectioned off room where her longtime section sits.
Peggy Bailey, 81, has been waiting tables in Catonsville since 1967. She is retiring soon from Jennings Cafe, where her longtime section is called “Peggy's Parlor.” (Kaitlin Newman/The Baltimore Banner)

Through joys and sorrows, Miss Peggy has been a constant in this cozy, wood-paneled tavern on Frederick Road since 1979. She’s been honored by Zagat’s, featured on TV’s “Today” show and, perhaps the greatest honor of all, served as grand marshal of Catonsville’s famed Fourth of July parade. She’s also buried her husband, her mother, and, last year, her youngest son. She’s survived two robberies and knee and hip replacements.

The Baltimore Banner thanks its sponsors. Become one.

But last spring, as Miss Peggy made her way back from a smoke break, a strong wind knocked the restaurant door against her back. Bailey fell and spent a week in the hospital. She hasn’t been able to bounce back.

So now, at 81, it’s time for Miss Peggy to retire.

Bailey is heading to Ohio to see how she likes living with her son and his family. Before she goes, Steve Iampieri, the owner of Jennings, is throwing a party in her honor this Saturday.

For Bailey, the work is not about earning tips, but building connections. The restaurant has been her window on the world, a place where she could make people’s lives a little brighter.

“It’s more than just serving food and picking up money,” said Bailey. “In order to be a good server, you have to love to do it. And you have to love people.”

The Baltimore Banner thanks its sponsors. Become one.

Bailey is so well known here that when the cafe’s former owner, Omar Jennings III, expanded the restaurant, he named the new room “Peggy’s Parlor.”

“It was a little crazy how much everyone loved her,” said Jennings. “People ate there just because they wanted to see her.”

When Iampieri bought the cafe from Jennings in 2017, he made some changes. He tweaked the name (it’s now Iamp’s at Jennings Cafe). New carpeting. More beer taps. But he had to keep Miss Peggy, whom he had long admired. “She treats people like they’re guests in her house,” he said.

A retirement party is planned on Saturday Nov. 4, 2023, at Jennings Cafe for Peggy Bailey, known affectionately as “Miss Bailey.” (Kaitlin Newman/The Baltimore Banner)
Owner Steve Iampiri discusses the important role that server Peggy Bailey has played at Jennings Cafe in Catonsville, where she has worked since 1979. Bailey is retiring and moving to Ohio to be closer to her family. (Kaitlin Newman/The Baltimore Banner)

Part of Miss Peggy’s magic is that she remembers everyone’s order without taking notes. “If you’re writing, you’re not looking at the customer,” she said. “You just need to picture it in your mind.”

Mohler said he has seen Bailey recall the orders of people who haven’t been in the cafe for months. “You could come in two months later and she’ll say, ‘Cheeseburger, medium, hold the onions,’” he said.

The Baltimore Banner thanks its sponsors. Become one.

On Monday, as Bailey chatted with two Baltimore Banner journalists at the cafe, customer Donna Brohawn swooped in for a hug. She’s been coming here since her daughter, now 35, was in second grade.

Miss Peggy rattled off the family’s favorite order from years past: “Oyster stew. Grilled cheese and a salad, ranch dressing. Chicken livers.”

Bailey’s life has not been easy. She was born to a 15-year-old mother and alcoholic father in North Carolina. She started working in tobacco barns at the age of 9. (”Now that was real work,” she said.) Her first serving job came in 1956, when she was 14; she worked as a carhop at a drive-in restaurant. Around that time, her mother fled from her father and moved to Baltimore; Bailey joined her after graduating from high school.

Her first job in Baltimore was at a Park Heights Kosher deli, Duke & Lou’s. She told the owner she wasn’t familiar with Kosher food, but he said not to worry. Then the first customer she waited on asked for a tongue sandwich. “I said, ‘Go to hell, you sonofabitch!’” she recalled.

Peggy’s Parlor is a shrine to waitress Peggy Bailey, affectionately known as Miss Peggy, at Jennings Cafe in Catonsville. Customers say the retiring Bailey has always treated them like family. (Kaitlin Newman/The Baltimore Banner)
Honors for “Miss Peggy” Bailey grace the wall of Peggy’s Parlor, a section of tables at Jennings Cafe in Catonsville. (Kaitlin Newman/The Baltimore Banner)

Assured by her boss that a tongue sandwich was a delicacy and not an indecent proposal, Bailey continued at the deli and grew to love it — and her new city. She later worked at the Pikesville Holiday Inn and the oldCandle Light Inn in Catonsville. She spent many years at the long-shuttered Middleborough Inn in Essex.

The Baltimore Banner thanks its sponsors. Become one.

Bailey lived with her mother, who was also a beloved waitress, her husband, who followed her here from North Carolina, and two sons. After her husband died suddenly during heart surgery in 1978, Miss Peggy started picking up lunch shifts at Jennings Cafe.

After the lunch rush, she would drive her navy blue Thunderbird across town to the Middleborough Inn for the dinner shift. Then she would drive home, vacuum, launder, starch and iron her clothes, sleep briefly, and get up to cook breakfast — as well as a full dinner for her boys to eat when they got home from school.

Bailey continued the exhausting schedule for more than a decade. In 1989, she left the Middleborough Inn. She has worked only at Jennings ever since.

Miss Peggy prides herself on speaking the truth about the restaurant’s dishes. If something isn’t good, she’ll tell you. And if you still order it, that’s your problem.

“My word is gospel. I will tell you that right now,” she said. “When I tell you something and you don’t listen, that’s your mistake. Not mine.”

The Baltimore Banner thanks its sponsors. Become one.

Miss Peggy’s candor and humor kept customers coming back, said Margaret Bowler of Catonsville, a longtime patron. But it’s her warmth that matters most. Bowler and her late husband, Michael Bowler, a former Baltimore Sun editor, would eat at one of Miss Peggy’s tables once a week with a group of friends.

Miss Peggy visited Michael Bowler at a rehabilitation center when he was ill, Margaret Bowler recalled. “She really does care about people,” Bowler said. “She’s genuinely interested in them.”

That’s the hardest part of retiring, Bailey said: “I miss my people.”

Still, she’s looking forward to spending time with her family in Ohio, especially her 8-year-old great-granddaughter.

Until then, she is savoring a little more time with her other family, the ones she has served french fries and shrimp salad all these years.

Various photos, works of art and drawings in waitress Peggy Bailey’s likeness adorn the walls of Peggy’s Parlor at Jennings Cafe in Catonsville. Bailey is retiring soon from the restaurant where she’s worked since 1979. (Kaitlin Newman/The Baltimore Banner)
Peggy Bailey is a self-proclaimed Miller girl; when asked what her favorite beer is she responds with Miller High Life.
Longtime Jennings Cafe waitress Peggy Bailey is a self-proclaimed “Miller girl,” citing the American lager as her drink of choice. Bailey is retiring sooner from Jennings, where she has worked since 1979. She is shown at the restaurant on Monday, Oct. 30, 2023. (Kaitlin Newman/The Baltimore Banner)
“Miss Peggy” Bailey gets a visit at Jennings Cafe in Catonsville from a longtime friend and customer, Donna Brohawn, on Monday, Oct. 30, 2023. (Kaitlin Newman/The Baltimore Banner)

As Miss Peggy sat at Jennings this week, sipping her drink of choice, Miller High Life, another longtime customer waved goodbye.

“You tell your mother I said, ‘Hi’ now, you hear?” said Miss Peggy. “Bye now, sweetheart.”

julie.scharper@thebaltimorebanner.com

Julie Scharper is an enterprise reporter for The Baltimore Banner. Her work ranges from investigations into allegations of sexual harassment and abuse to light-hearted features. Baltimore Magazine awarded Scharper a Best in Baltimore in 2023 for her series exposing a toxic work culture within the Maryland Park Service.

More From The Banner