September-October 2018 | SMOOTH OPERATION

Woody's Dewey Beach Bar & Grill owner Jimmy O'ConorSMOOTH OPERATIONSMOOTH OPERATIONSMOOTH OPERATIONJimmy enjoys a bite with Bob Yesbek.



Under Jimmy O’Conor’s leadership, Woody’s Dewey Beach Bar & Grill has the uncommon distinction of being just as popular with locals as it is with visitors

Written By: Bob Yesbek | Photographer: GRANT L. GURSKY

Baltimore-born Jimmy O’Conor really had no choice but to serve a killer crab cake. After all, very few towns are as militant about their crab cakes as Charm City. Animated discussions — often fueled by beer — will certainly include such names as the sadly gone Gunning’s (huge orbs laced with Old Bay; make mine fried, thank you), Faidley’s (brave the line at Lexington Market for a softball-size behemoth on a fresh roll, then stand there and eat it), and of course, Obrycki’s (now closed, but they dished up meaty cakes since ’44). There are others, obviously, but these are the ones that stand out for me.

The pocket-sized Woody’s Dewey Beach Bar & Grill in Dewey Beach is Jimmy’s pride and joy. And he has certainly paid his dues. At the tender age of 15, he started working at a Rustler Steak House. By 17, he was flippin’ steaks as the broiler chef. After 10 years as a bartender and general manager of various Baltimore hotspots, Jimmy decided he was finished with the food business. But as is so often the case, it wasn’t finished with him. Big Mike’s Frozen Tundra, a little joint tucked away on the east side of Coastal Highway in Dewey Beach, was about to be offered for sale. And thus was born Woody’s East Coast Bar & Grill.

This paragraph was supposed to be about Woody’s particularly tasty crab cakes and burgers, but a digression is in order: In June 2011, Jimmy found himself in dire need of a kidney. In order to overcome donor incompatibility, a kidney-exchange program facilitated the donation of one of his then-girlfriend’s kidneys to a woman in Baltimore. In turn, the woman’s daughter donated one of hers to Jimmy. This amazing program — where all four operations are performed simultaneously — has saved many lives. When I called Jimmy to fact-check that his “then-girlfriend,” who participated in the transplant, is now his wife, he said yes, then quickly added, “but that’s not why I married her.” I like the way this guy thinks. 

After that heartwarming story, it seems anticlimactic to jump right back into crabmeat and ground beef. But this is the Flavors section, after all, and that’s why we’re gathered here today. Jimmy is a tireless hands-on owner. Though his intention was for Woody’s to be known for the ultimate hamburger, it turns out that the crab cakes consistently pack ’em in. Both the burger and the crab cake sandwich benefit from a grilled roll that gently caresses its contents with a fresh, eggy consistency. As for the crab cake itself, chunks, chunks and more chunks of lump crabmeat are held together with... well, I tasted only crabmeat, with little or no filler or mayo. (Truth be told, I couldn’t call myself The Rehoboth Foodie if I didn’t know exactly how Jimmy does it. But I’ll leave it for you to guess.)

The platter sports two baseball-sized cakes that are very well-portioned for the approximately $33 price tag. On another visit, I ordered the crab cake sandwich. (See? That way I can get the crab cake again, but still act the part of a proper reviewer by saying that I ordered something different.) The expected orb of lightly seared crabmeat appeared, but the real surprise was the roll. Regulars at know how I whine about rolls. They are an integral part of a sandwich, and anything served on a stale or pretentiously too-firm roll must be immediately destroyed.

You don’t want to miss the Dewey Dunker. Thinly sliced beef is presented on one of those great rolls with a side of au jus. Think French dip without the onions and cheese. Another sleeper at Woody’s is the Chicklet; a properly fried breast is slathered with regulation buffalo sauce and topped with blue cheese. Okay, a little pedestrian, I admit, but deliciously executed and on that nice roll to boot.

For the crab cake-challenged, there are also the cheesesteaks. Both the chicken and the traditional Philly versions are stuffed with quality ingredients, sautéed onions and any number of cheesy choices. One of the stars of the appetizer menu is the fried pickles. The dill spears are evenly coated with a crispy spiced breading that perfectly complements the acidic pickle. They are quite good and are served with “Woody Sauce.” Don’t ask. I have been sworn to secrecy and Jimmy knows where I live.

Woody’s Dewey Beach Bar & Grill is located in the heart of Dewey Beach at 1904 Highway One, on the east side. The food and friendly attitude there are well worth beating back the perpetually tipsy Dewey summer crowds. Woody’s is open year-round, from 11 a.m. until 1 a.m., serving lunch and dinner Sunday through Thursday until 10 p.m. and until 11 p.m. on Fridays and Saturdays. The icing on the cake is the late-night menu dished up until 1 a.m. It never hurts to give a call in the off-season at (302) 260-9945. This IS the beach, after all, so ya never know.

Posted On: 9/10/18 9:48 pm
The best CC on the planet! Jimmy is an awesome guy he deserves the accolades he runs a great spot. Big heart, great guy.