Upstate NY hound will be in Annapolis for a workshop which leaves us free each of 5 nights for dinner. What are some "should not miss" chow-worthy spots? Will have a car; while cost is not an issue, would also like to sample some down-to-earth, local joints as well.
Vin909, Wild Country Seafood, Cantler's and maybe Chick and Ruth's for some MD crab soup. I haven't been to O'Leary's in a while, so not sure if it is still really good.
Here is my report on Annapolis dining. Got to town mid-afternoon Sunday and, after checking into the hotel, met my daughter who drove over from the DC area where she lives. We both wanted crabs, so we did dinner at Cantler's, which is across the Severn River from the main peninsula on which Annapolis sits, down a narrow, winding residential road that leads to a creek side complex of buildings that constitute the restaurant. While it was crowded and noisy, we were immediately seated (without having had a reservation) outside under a canopy at one of many long, communal-style wooden tables. We couldn't help noticing the piles of bright red (from Old Bay seasoning) crabs on plain brown paper in front of most diners, as well as the distinct sound of small wooden hammers crashing down on crustacean bodies. We ordered a dozen large crabs ($55), side salads, a basket of hush puppies, and beers. Neither the salad nor hush puppies (small, overly sweet, and without much textural heterogeneity) were noteworthy. The crabs, however, were quite tasty, despite the work it took to extract meat from the shell. This was my first experience with steamed crabs, and while I could fairly easily break open the large claws to get a hunk of flesh, it was much more gratifying to slowly pull out the tender, sweet meat from the carapace. As a novice, it took me nearly 90 minutes (and two beers) to work my way through my 6 crabs. I would recommend Cantler's to anyone who seeks the "real" (as opposed to tourist-fied) crab experience.
The next morning, I had a late breakfast at Miss Shirley's Diner on West Street. This is a relatively upscale "diner" with an interesting, Southern-influenced menu of breakfast and lunch items, as well as a full bar. I debated among three different choices and settled on a breakfast sandwich of fried green tomatoes, smashed avocado, applewood smoked bacon, cheddar cheese, and a fried egg on thick slices of pumpernickel, with a side of stone ground grits. The sandwich was delectable, the crunch of the bacon balancing the tangy tomatoes and creamy avocado. The grits were not as distinctively "stone ground" as those I am used to (e.g., from the Hominy Grill and other restaurants in Charleston, SC). Nevertheless this was a satisfying meal that stayed with me through dinner that night.
Most of my remaining meals (2 dinners, 4 breakfasts and 4 lunches) were at Loew's Hotel, where the restaurant West is located, and where 20 of us were staying and attending a workshop). The dinners (lump crab cakes on fried green tomato one night, and a perfectly medium rare beef tenderloin the other) were outstanding, the lunch buffets were sumptuous in quality and quantity, and the breakfasts so-so (due to the merely ordinary quality of the croissants, muffins, and Danish). Dinner at The Metropolitan (rockfish, a delicious vegetable medley, and jasmine rice) was very good, as was my meal at Pusser's, in the Annapolis Marriott on the waterfront. My entree was Halibut Annapolitan, a generous piece of perfectly cooked halibut topped with just the right amount of lump crabmeat and a bechamel (?) sauce. Interesting ambience - we sat outside right along the water but adjacent to a relatively rowdy bar full of 20-somethings. Descriptions of this place that you can read on Yelp reviews are spot on regarding the noise level, but all 8 of us 50- and 60-somethings really enjoyed our meals!
I would have liked to have tried Vin 909, but with 8-10 of us wanting to find together, we chose to walk at her than split up to drive. I will just have to put it on the itinerary for my next Annapolis visit.
re: Mike in Rhinebeck
The Crabs are not red from the Old Bay. They turn bright Red when Cooked just like Crawfish or Lobsters.
The Sides at Cantler's and most Crab Joints are not very good but they have good Steamers and Crab Soup when you want a little more than just Crabs.
I am a Native MDer and we go to Cantler's when we do not catch enough off our Dock.
I have family in Annapolis and visit there often. Chart House is always reliable for a nice dinner.
Sorry I missed your post. Another good choice is Lewnes steakhouse as well as Mikes Crab house although it is similar to Cantlers.
Excellent lunch of Tempura fried soft shell crab over mango salad, and a Dogfish 60 Minute draft, at Red Red Wine in Annapolis