A trio of Annapolis restaurants, the steal/deal of the month, and other secrets [classic article]

Annapolis has three restaurants under the same ownership and like three sisters, they each have their own character and charm. The grande dame of Annapolis’ historic eateries is Middleton Tavern (www.middletontavern.com ). Located right at City Dock, it’s been welcoming hungry customers since 1750. They even have a lifelong chef in the kitchen – Jimmy — who first took a job there in 1946. And though Middleton’s has some great old-school dining features and working fireplaces, it’s a comfortable, casual vibe. Not only is Annapolis Week going on right now with a $29.95 dinner, there’s another fantastic deal going on: “Customer Appreciation Month” – a 3 course lunch with sides AND a glass of house wine for $14.10! I was very happy to be able to taste this project. Unlike many places where the prix fixe is comprised of fillers and plain items, Middleton’s really goes all out in their appreciation.

Oysters are classic at Middleton’s and the Oysters Rockefeller is subtle and sweet. The Hollandaise sauce and spinach pay homage to the best quality shellfish. If you haven’t tried Bluefish, here’s a great place to start. Because they get the crème de la crème, it doesn’t have that “fishy” taste that shoos many folks away from it. It’s simply cooked with pepper, served with a white pepper cream sauce and nutty-like crackers.

Pecan-encrusted trout has a butter sauce with sweet red peppers and artichokes. Very gourmet! Their trout is mild and the sauce adds a creamy, yet tangy note. As famous as Middleton’s is for seafood, you’ll be tempted by their Southern fried chicken – three pieces, yet! – served with homemade buttery mashed potatoes, chicken gravy, and coleslaw. If Middleton’s sold their coleslaw in stores, people would be filling their fridges with it. They include minced red onion and other secret things, elevating it above picnic fare.

If you order from the regular menu, the scallop sliders are an innovative take on the popular presentation. Crunchy fried onion adds just the right compliment to tender, sweet scallops.

Middleton’s makes their own crème brulee as one of the dessert choices. If you are ordering off the regular menu, they have a few tableside-prepared desserts, like glamorous restaurants of old. There are also salads and entrees available for a tableside show.

In a cocktail mood? Their new Middleton Pickled Bloody Mary has a veritable sweet pickled salad bar garnishing their very own Bloody Mary mix. Taking great care with its flavor, it doesn’t have the bitter taste that commercial mixes with harsh vodka have. And if you really want to be like a local, you gotta get a fresh oyster shooter. Try it with the Sam Adam’s Oyster Ale, made ‘specially for Middleton’s. It’s mild and doesn’t interfere with the shooter’s flavor.

O’Brien’s (www.obriensoysterbar.com ) is a raw bar/sports bar by weekday, and Annapolis’ biggest dance floor with live bands on weekend nights.

Here’s a secret many Annapolitans don’t even know about: upstairs is Ob’s Prime (www.obsprime.com ), a swanky late 50’s/early 60’s style steakhouse. With an incredible two-story fireplace, vintage light fixtures, and curved sofas, it has a very different ambiance from anywhere else you’ll find in Annapolis. Additionally, very interesting smaller rooms can be booked for private parties. At this time, Ob’s is only open on weekends: reservations are definitely recommended.

Here’s another secret: there’s new FREE transportation in Annapolis, so you can park anywhere within about a 1 mile radius. ECruisers (www.ecruisersllc.com ) will pick you up – just tip your driver. It’s a neat, completely electric vehicle that zips up like a tent in inclement weather. They do door-to-door service and it’s perfect if you want to bar hop, shop, or whatever.