Historically, Annapolis has served as a home to the rich and powerful; it continues to draw a steady stream of wealthy visitors and boaters, and as the state capital, a regular menu of politicians, lobbyists, and residents who have the money to purchase homes in this charming town. As such, numerous fine and upscale eateries cater to this clientele and feature a range of dining options, with many focusing on fresh offerings from Chesapeake Bay, including oysters and Maryland’s state catch, rockfish.

For seafood and Maryland’s signature dish, the crab cake, few restaurants can be topped by O’Leary’s Seafood (310 3rd St., 410/263-0884, www.olearyseafood.com, Mon.-Sat. 5-11 p.m., Sun. 5-10 p.m.), an upscale eatery with a range of fresh choices on the menu prepared New American style, including a lobster “cappuccino” that’s a bisque treated like a beverage, tuna sashimi, duck, and, of course, jumbo lump crab cakes.

Carrol’s Creek Café (410 Severn Ave., 410/263-8102, www.carrolscreek.com, Mon.-Sat. 11:30 a.m.-4 p.m. and 5-10 p.m., Sun. 10:30 a.m.-1:30 p.m. and 3-9 p.m.) is popular with locals for its cream of crab soup and waterfront dining.

To dine in historic ambience and enjoy a range of pub fare, seafood, and even high tea, check out two historic way stations that served the colonists. Middleton Tavern (2 Market Space, 410/263-3323, www.middeltontavern.com, Mon.-Fri. 11:30 a.m.-1:30 a.m., Sat.-Sun. 10 a.m.-1:30 a.m.) played host to Washington, Jefferson, and Franklin; today, its location adjacent to the City Dock, outdoor dining areas, and dark traditional spaces are continuously packed with diners and revelers. If you’re an oyster fan, try the oyster shooter, an oyster served in a shot glass with cocktail sauce and vodka and served with a beer chaser.

For more genteel entertainment, consider tea and scones or High Colonial Tea at Reynold’s Tavern (7 Church Circle, 410/295-9555, www.reynoldstavern.org, lunch and afternoon tea daily 11 a.m.-5 p.m., dinner Wed.-Sun. 5:30-9:30 p.m.), which contains the Sly Fox Pub (Sun.-Thurs. 11 a.m.-midnight, Fri.-Sat. 11 a.m.-2 a.m.). It is the oldest “ordinary” in the city, an early Tidewater-style tavern built in 1747 that also has a full restaurant and basement bar that serves lunch and pub fare in the evenings.

A trip to Annapolis or anywhere in the vicinity is not complete, at least for my family, without a visit to Chick & Ruths Delly (165 Main St., 410/269-6737, www.chickandruths.com, Sun.-Thurs. 6:30 a.m.-11:30 p.m., Fri.-Sat. 6:30 a.m.-12:30 a.m.), a venerable institution that draws customers with its stacked sandwiches, burgers, and ginormous milk shakes that taste like they’re made purely from a gallon of ice cream. The menu features a range of sandwiches named for Maryland state figures, military heroes, and international stars, many of whom have eaten in this narrow, bustling circa-1950s lunch counter. Staffers are friendly and chatty, regardless of how packed the place gets, and it stays busy throughout the day, with local lawmakers popping in for breakfast and lunch, visitors getting an afternoon snack, and midshipmen looking for a break from King Hall. The milk shakes are a must-try.

If you have a car or access to one, consider heading to Cantler’s Riverside Inn (458 Forest Beach Rd., 410/757-1311, www.cantlers.com, Sun.-Thurs. 11 a.m.-11 p.m., Fri.-Sat. 11 a.m.-midnight) for a taste of pure Chesapeake Bay—steamed crabs, rockfish bites, slaw, french fries, and cold beer served in cans. This remote waterside spot is accessible by road or by boat, with plenty of draft for a sailboat (14 feet MLW and 15 slips). Patient servers will instruct you on how to eat a blue crab if you’re not familiar with the process; New Englanders accustomed to the ease and reward of eating a steamed lobster tend to get the most frustrated by the labor-intensive effort.