Nor'easter — July 2, 2010
Change Language:
Dock & Dine In Annapolis/Eastport
Paul Esterle

Dock and Dine in Annapolis

I had a choice to make when writing this article. I had enough room to simply list a bunch of restaurants in the Annapolis area or do something a little different. What I decided to do was to query some of my Annapolis-savvy friends about their favorite eating spots that were readily accessible by boat. Here are their responses, in no particular order:

Davis Pub

“Where there are no strangers, just friends you haven’t met.” This little hole-in-the-wall bar/pub/ restaurant is an Eastport favorite of many of the sailboat racers, probably because they’re too tired to walk any farther. Nothing fancy; great crab cakes, burgers and onion rings along with what’s needed to wash it all down after a hard day of racing out on the Bay. 400 Chester Ave.

Annapolis, MD 21403

(410) 268-7432 Boatyard Bar & Grill If you can remember the word on the street that the Boatyard was going to be the “new Marmadukes,” this isn’t your first time here and you aren’t a newbie. Marmadukes was a famous (or infamous) Eastport dive catering to the sailboat crowd. It was torn down and replaced by a Ruth’s Chris Steakhouse. Another favorite haunt of the sailboat racing crowd, the Boatyard features videos of the day’s racing fresh from the Bay. 400 4th Street Annapolis, MD 21403-2504

(410) 216-6206

Chick & Ruth’s Delly

This is one of my picks. I can’t go to Annapolis unless I take my wife here for an old-fashioned malted milkshake; the best she’s ever tasted.

The sandwiches are pure deli-delicious and named after local politicos and celebrities. Ted Levitt, son of Chick and Ruth, now runs the place.

He is also an accomplished magician and often entertains the kids (and adults) as they eat. The Pledge of Allegiance is recited every morning at 8:30 (9:30 on weekends). 165 Main Street Annapolis, MD 21401

(410) 269-6737; fax (410) 269-6738

Joss Cafe & Sushi Bar

Joss garnered several votes as the best place for sushi in Annapolis. Best of all, it’s on Main Street within easy walking distance from Ego Alley. 105 Main Street Annapolis, MD 21401

(310) 263-4688

Middleton Tavern

Talk about history, the Middleton Tavern has it in spades. It has been in Annapolis since 1740 and sold to the Middletons in 1750. The likes of George Washington, Thomas Jefferson and Benjamin Franklin crossed the tavern’s threshold.

The tavern is famous for its local seafood: crab cakes, oysters and clams. During the summer, and especially during the boat shows, the outside seating is a great place to people-watch while enjoying the tavern’s fare. 2 Market Space Annapolis, Maryland 21401 410-263-3323 410-269-1256 301-261-2838


Pusser’s is located in the Annapolis Marriott Waterfront Hotel and faces Ego Alley. If you like, they have an outside deck so you can watch the happenings in Ego Alley as you eat. Depending on the skill of the boater, it can be quite entertaining.

Pusser’s is famous for its “Painkiller” rum drinks, served by the bucket-full during boat shows. The best place to watch them breakup the boats shows is from Pusser’s top deck, with a Painkiller in hand. 80 Compromise Street Annapolis, MD 21401

(410) 626-0004

Cantler’s Riverside Inn

Cantler’s was given a thumbs-up by several as the best place in the Annapolis area for crabs. Not technically in Annapolis, it is on Mill Creek off Whitehall Bay, not far by boat. They offer free dockage for restaurant patrons. By all reports, it is not to be missed. 458 Forest Beach Road Annapolis, MD 21401 410-757-1311


Well, there you have it, the results of my informal and probably biased survey. If you have your own favorite, drop me a line at and let me know.