The best offbeat escapes in the Northeast..

I don’t know what to write about first: Barbara Esmonde or her food. Both are equally astounding, unique, and brilliant. Just the idea that Esmonde – who ran in circles with Bobby Flay, cooked at the James Beard House in NY, helmed the kitchen at an Upper East Side NY restaurant, and competed on Chopped –  would wind up in this tiny, population 300 town of Betterton MD, is, as my kids would say “amazeballs.” Each move and each job taught Esmonde “what to do and what not to do” when running her own restaurant. She cooked in Oregon, studied in Italy, managed a Country Club restaurant in Chestertown, and one day she walked into this café for sale on a bluff overlooking Betterton Beach and the Chesapeake Bay, and she was smitten. Esmonde has lots of friends willing to help her, so she started a “non-wedding” Registry on Amazon where they could contribute and purchase all the appliances and equipment she needed for her new endeavor. 

Barbara’s On the Bay – Great Food in Betterton, Maryland

"When I noticed the bartender whipping up a Bloody Mary for a regular who had yet to even enter the building, I knew that I was going to enjoy my meal at Barbara’s On the Bay. My first impression was right. "


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. 

40 Insidery Things to Do In Maryland’s Upper Chesapeake Region

  Eat at Barbara’s on the Bay, in the tiny town of Betterton – population 300. Philly-born, New York chef, Barbara Esmonde, ran in circles with Bobby Flay, cooked at the Beard House, and competed on Chopped before landing in Maryland. One day she walked into this café for sale on a bluff overlooking Betterton Beach and the Chesapeake Bay, and she was smitten. Since then Barbara’s on the Bay has been wowing diners with exemplary service and eclectic and outrageously good food, like the signature Aberdeen Rumble – dry rub flank steak, caramelized onions, from scratch potato sticks, roasted red pepper sauce on Ciabatta Roll; a Holy Cow! of a meal meant for guys with hearty appetites, or girls who don’t want to miss out. Her Scotch Eggs, a crunchy-soft version of the Irish Pub staple is the perfect snack, as is the orgasmic Pretzel slathered in warm crab dip. You’ll want to eat everything, but no worries. You can work off those calories by striding a few times down to and up from the pristine Betterton Beach - the prettiest beach on the upper Chesapeake.

From Wall Street to the Bay, Barb Makes Her Mark

By Mary Lou Baker // Photography by Tony Lewis, Jr.

The Little Engine That Could, the popular children’s book with its mantra, “I think I can, I think I can,” is the inspiration for Barbara Esmonde, chef-owner of Barbara’s-on-the-Bay in Betterton, Maryland. I drove through flat farmlands and little villages to meet with Esmonde at her charming waterfront restaurant on a hillside overlooking the Chesapeake. We chatted over brunch: a Bloody Mary garnished with a pretzel stick as an edible stirrer, Scotch eggs, and eggs Benedict dressed with silken Hollandaise sauce she makes herself. Vivacious and verbal, this is a woman in love with food, her restaurant, and her customers.