eat local

A Watershed Moment in Chestertown

By & / Photography By | December 01, 2021
Share to printerest
Share to fb
Share to twitter
Share to mail
Share to print
Watershed Alley Chef/Owner Rodney Scruggs (left), with his wife Pastry Chef Lisa Scruggs, and Chef Thomas Kaylor.

Chef Rodney Scruggs sits in one of the many curve-backed upholstered chairs that fill the two floors of Watershed Alley, his new restaurant in Chestertown, Maryland. He exudes the optimism of a man on a winning streak; indeed, he is most certainly on one, returning to Chestertown after many years at The Imperial Hotel to open Watershed Alley on High Street in historic downtown on Labor Day.

“It was a project three years in the making,” he tells me from the unassuming aesthetic of the private dining room on the restaurant’s vast second floor. Despite the ongoing construction, it was easy to see a vision of elegance, something that was even more visible upon their grand opening.

The Chef’s vision bodes well for Chestertown, where for years the number of fine dining restaurants has been limited to a number you can count on one hand. “My goal is to become an anchor in Chestertown, one that is understated and welcoming with a clean menu,” Scruggs says. “We will be accessible and not so serious that we put off our guests.”

To understand Chef Rodney’s optimism requires you look no further than his storied past, with scores of accomplishments in the restaurant world. The consummate chef of simplicity, Scruggs explains that he didn’t get his start in the restaurant industry at all, but rather began as the chef of his home as a child.

“I cooked for my family at first and knew early on what my calling was. Later, after joining the military was not an option, I took commercial cooking classes in school, studying immersively under several serious chefs at the TC Williams School, then later at Newberry College in Brookline, Massachusetts. I honed my craft working with these great chefs, sometimes spending hours and hours in the kitchen,” he recalls wistfully. “I was fortunate to later work with acclaimed chefs like Jeff Buben in Washington, DC. In fact, I have been fortunate over my lifetime to work with some great sous chefs and chefs.”

Born in South Carolina, Scruggs explains how he grew to develop menus of food that were celebrated and in demand by his guests at numerous restaurants. “The pursuit of simplicity was an early instinct for me,” he says, walking me through the sparkling new kitchen which houses an enormous Hestan stove, “and that instinct has governed the simple menu I will lead at Watershed Alley. It will be a concept of 5: 5 first courses, 5 main courses, and 5 desserts. The wines will also follow this concept with 5 reds and 5 whites.” Dishes include a succulent braised short rib, hearty grilled Roseda Farm New York strip steak, and classic vanilla crème brûlée with blueberries, but will change often. “I’m also planning live jazz, guest chefs, and wine nights with prominent wine makers,” the chef adds.

But if simplicity is the factor by which this chef is succeeding, so too is his command of the guest experience, having played a role in every inch of the lush interior, along with his business partner Wendy Culp.

“Wendy knew what she wanted,” Scruggs tells me as we stroll through the dining room, “and miraculously, we saw eye to eye on every detail: from the stove to the skillets, from the cutlery to the glassware, even to the patterned fabrics of the seating.” The collaboration, as he describes it, visibly reveals a great attention to detail: every room is appointed with craft and care, including the bathrooms.

In addition to the elegance and sheer brilliance of the interior architecture, Watershed Alley is also an homage to Chestertown and the Chesapeake Watershed Region in the way in which local artisans are celebrated in every sight line throughout the purview of the space. Wooden tables and a grand wooden staircase were handcrafted nearby by Vicco Van Voss, and the plethora of paintings throughout both floors are the product of local artists, including Marcy Dunn Ramsey, Annie Singer and Bonnie Howell. Along one wall near the entrance is a driftwood sculpture made from donated wood from the area. Ingredients will be sourced from local farms and seafood from local waterways.

“We wanted to celebrate the region, and in particular Chestertown and the Chesapeake watershed area,” Wendy Culp says. “And Rodney was the perfect choice for the chef role because of his love of Chestertown and his interest in coming back with his wife, Lisa Scruggs, who serves as the restaurant’s pastry chef.”

Chef Rodney speaks with a laser focus on the simplicity of his culinary mission, “We want to capture the essence of Chestertown,” he notes. But his ease comes from a series of great successes as chef of the famed Washington, DC restaurant The Occidental, the destination often for Presidents (his first stint was at age seventeen, the youngest on staff). “We were successful there,” Scruggs says, “and what we did increased our audience greatly each year.”

Moreover, Chef Rodney Scruggs presents as a man with a clear vision and indeed the culinary experience to back up what will be Chestertown’s highest end, fine dining establishment. “Watershed Alley will be unassuming and elegant, a reflection of Chestertown itself and the people here.”

When asked what this moment means to Scruggs, he explains that the timing was simply right for this, “We had many names in the hat for this restaurant, but when I explained that, for me, coming back to Chestertown to open a restaurant of this nature was a watershed moment—I knew at that moment that Watershed Alley had to be the name.”

Watershed Alley opened on Labor Day weekend to rave reviews from local residents like Susan Miller and Andy Gray who report, “The food, wine and the atmosphere are sublime; we waited a long time for this restaurant to open, and it was worth the wait.”

What’s more, the dining room, visible from High Street through a facade of windows, reveals a packed house every night, suggesting Scruggs’ and Culp’s gamble netted a clear win. “I do it because of my passion for this,” Scruggs says, something that’s palatable with every bite of his delicious food.

Watershed Alley
337 High Street, Chestertown, Maryland
443.282.9797
Facebook  Instagram

We will never share your email address with anyone else. See our privacy policy.