Watershed Alley: Local, welcoming and refined in Chestertown

By Laura Walter
Posted 6/10/24

First walking into Watershed Alley almost felt like a metro experience. It looked elegant and hip, with exposed brick, glass art and curated lights.

Meanwhile, I was sweating down to my sneakers …

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Watershed Alley: Local, welcoming and refined in Chestertown


First walking into Watershed Alley almost felt like a metro experience. It looked elegant and hip, with exposed brick, glass art and curated lights.

Meanwhile, I was sweating down to my sneakers in the springtime heat. I felt neither elegant nor hip.

The restaurant staff didn’t bat an eye. In this cool, lovely atmosphere, they truly just want you to enjoy some good food. You can order bison from Virginia or salmon from the Faroe Islands—but you don’t have to dress fancy to eat well.

“We have people come in in camo all the time,” said General Manager Kyle Turner Whitehair. “Come as you are! We want elegance [in food], but absolutely everyone is welcome here. You don’t have to put on your Sunday finest or feel concerned … We are here to meet people for a good meal and a good time.”

Watershed Alley brings a high treatment of even familiar dishes, like chicken and potatoes. The chicken breast was moist with flavorful golden skin (and a high quality, humanely raised Green Circle bird). Crispy potatoes were roasted in duck fat. A creamy mustard sauce marinated, but didn’t overwhelm the dish.

I’m glad I ignored my usual desire to avoid food that “I could make at home!”

What do the staff enjoy? “Oh my god, it’s all so good,” one person gushed.

For an appetizer, we tried sliced prosciutto with tangy balsamic dressing and greens, fig syrup, creamy burrata (soft Italian cheese wrapped in mozzarella) and a grill-toasted baguette.

Watershed main courses include jumbo sea scallops, pork or veal. But the recipes are elevated: braised free-range lamb shank with baby vegetables, creamy herb-mascarpone barley and red wine jus; or tender free-range bison with gochujang marinade, zucchini, olive tapenade and eggplant puree. This month’s appetizers included carrot and rabbit ravioli with garden vegetables; charred octopus with crispy pork belly; and asparagus and beet salad with prickly pear/avocado vinaigrette.

Watershed Alley has really expanded its wine lineup over the past year, too, under the guidance of beverage director Turner Whitehair. She aims for wines that are considered sustainable, organic, biodynamic or natural—especially highlighting small family producers, but still produced well and for a refined palate.

Creative cocktails and mocktails are also a welcome addition to the lineup, and my strawberry “nojito” was refreshing on this hot day.

The menu is ever changing, up to six times a year, to keep flavors and ingredients truly seasonal.

“Everything they can get is hyper-local as possible,” said Turner Whitehair. “The [chefs] have great relationships with the purveyors and make really elegant food it.” This starts with brainstorming at the weekly famers’ market literally across the street—then ordering produce, often from less than 20 miles away, especially during Eastern Shore summers.

Diners can see the cooks at work in the open-air kitchen.

“We as a kitchen want people to come over and say hello. We didn’t want to hide,” says Rodney Scruggs, one of the chefs/cofounders.

Scruggs insists it’s not fine dining—it’s “refined dining,” or a refinement of familiar dishes. Spinoffs include crab cake with avocado mousse, tiramisu layered with dark berries, or salad with almonds and citrus fruit (but specifically avoiding the standard grapefruit that would otherwise react with many clients’ medication).

“We want people to feel they’re somewhere that’s sophisticated … but you’re getting bang for your buck,” said Scruggs. That’s why the clientele includes locals, cyclists, hunters and boaters.

Additional dining and event space fills the entire second floor—just beyond those elegant, organically carved wooden stairs.

Watershed Alley is located at 337 High Street, Chestertown, Md. Learn more at (443) 282-9797 and thewatershedalley.com.

Bay to the Beach: Byways is a regular column in which we explore interesting places and projects on the Delmarva Peninsula. Videos and more photos at baytobaynews.com/bay-to-the-beach-byways

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