Chesapeake Chef: Barbara’s on the Bay

How one woman started on Wall Street and ended up owning a shoreside restaurant in Betterton, Md.

by Nancy Taylor Robson

How one woman started on Wall Street and ended up owning a shoreside restaurant in Betterton, Md.

Barbara’s on the Bay in Betterton, Md., isn’t actually on the Bay—it’s halfway up a hill overlooking the Sassafras River and Upper Chesapeake—but it’s definitely Barbara’s. Artwork from Barbara’s home decorates the walls. An old sewing-machine stand that a friend gave her holds menus. The menu embodies her varied career—pub food (Scotch eggs) from her bartender years, Chesapeake-with-a-Philly-twist (crab dip in a big chewy pretzel) from her Chestertown Yacht and Country Club years, steak fajitas with local fresh produce (West Coast), and filet mignon with gorgeous mirepoix (NYC and Julia Child). The list hints at her range. While she’s tucked her popular restaurant into a small town on the Eastern Shore, her cooking chops were honed in New York City and food-forward San Francisco and Portland, Ore.

Yet chef Barbara Esmonde, a lively, dark-haired dynamo, didn’t set out to cook. She started out on Wall Street.“I was a receptionist and ended up as a mutual fund market representative,” she says. She loved New York but hated Wall Street. “Money’s not the biggest motivator for me.” She left finance during the 1987 crash to tend bar in McAleer’s Pub, her “local.” When the cook quit,
she stepped into the kitchen.

“One of my friends from McAleer’s was a chef, and he encouraged me,” she says. Another friend gave her his late mother’s “ton of cookbooks.” Then a restaurant opened next door. She signed on as line cook, and was off to the races. “When you work in a fancy New York City restaurant, you learn speed!” she laughs. To gain expertise, she volunteered at the James Beard Foundation where she met Bobby Flay. “After I did his dinner, he asked me to come work for him. So, I was really getting paid to learn how to run a restaurant,” she says. 

Flay opened doors for her. She was backstage with Letterman, went drinking with Emeril Lagasse, “before he was Emeril,” she says, and she cooked for Julia Child’s 80th birthday celebration. “She was so gracious,” Barbara recalls. “She came in the kitchen and pointed me out in that voice and said ‘Good for you!’ ”

In the early ’90s Barbara had her own kitchen in a restaurant on the Upper East Side where she learned how not to run a restaurant. “Your friends can’t all eat for free!” she laughs. By the late ’90s, she was on the West Coast where the food scene was exploding, but when her mom got sick, she came back to Philadelphia to take care of her and work as a private chef. Then, a neighbor told her about a job at the Chestertown Yacht and Country Club in Chestertown. She ran the kitchen, including budgets and personnel. “What I didn’t know is that I was plugging in the last pieces of the puzzle toward ownership,” she says. After four years, she decided to move on, and got a call from her friend, Todd Smith, of Todd’s Auto Body in Chestertown. “He said: “Go look at the place in Betterton,” she says. “[Realtor] Matt Hogan let me in the door, and I knew immediately! If you walk into a space and feel it, you’ll know it. I think that’s what it’s like to be in love. It was big enough to make some money, small enough to manage on my own, and the view!”

The view really is great, but it’s the food and the atmosphere that keeps ’em coming back. “I got the idea of being gracious to people from Le Cirque,” she says. “I remember [then owner Sirio] Massioni greeting me like I was an expected and welcome guest, and I remember that feeling.”

She’s recreated that feeling in a completely different place from self-conscious NYC. Barbara’s is warmly comfortable, and the attentive and friendly staff makes sure everyone feels at home. 

Leave the boat at the Betterton pier, walk up the hill into the shade and sit at the wide wooden bar for a drink before going out onto the pergola-shaded deck for a meal. If it isn’t too crowded, ask Barbara about the Amazon registry “shoe shower” she threw herself that helped outfit the place. In a howling nor’easter, sit inside, drink Irish coffee, chow down on an Eastern Shore po’ boy (crispy fried oysters or shrimp in white bread) or the Aberdeen Rumble (dry-rubbed flank steak with caramelized onions and cole slaw—yum.) and watch while the weather rages. Trade stories with whoever’s there. It’s a we’re-all-in-together kind of place that’ll feel like your “local.” h

Barbara’s on the Bay is located at 12 Ericsson Ave., Betterton, Md. Open Wed.–Sun. for lunch and dinner (summer and winter hours apply). Appetizers $9–$12; entrees $18–$30