Chick and Ruth's Delly
165 Main Street, chickandruths.com
Mornings at this downtown mainstay begin with a restaurant-wide recitation of the Pledge of Allegiance (8:30 a.m. on weekdays and 9:30 a.m. on Saturdays). In keeping with its posted idea that "democracy is a daily special and patriotism is always on the menu," the Delly's hearty sandwiches and entrées are named after governmental officials. For breakfast, try the Senator Nathaniel J. McFadden Corned Beef Hash ($9) or the Lieutenant Governor Anthony G. Brown steak and eggs platter ($15). If the ample-sized portions don't fill you up, wash your breakfast down with one of the signature colossal milkshakes or malts, weighing in at 6 pounds and served all day long. (The old-fashioned milkshakes are also available in two smaller sizes in case you don't have room.)
Back in 1814 Francis Scott Key, author of the National Anthem, graduated from the local St. John's College. The Maryland native was also married at the nearby Chase-Lloyd House (now open for public tours), before making his poetic contribution to history during the Battle of Baltimore in 1814.
7 Church Circle, reynoldstavern.org
A few minutes from the Maryland State House, this quaint three-room inn houses a tearoom, pub, and restaurant. Its pub grub includes authentic British favorites, such as bangers and mash (English pork sausage served over mashed potatoes with gravy; $14) and shepherd's pie (made with roasted lamb, peas, carrots, and fluffy mashed potatoes; $15). If you're looking for a slightly lighter lunch, try the tavern's famed Quiche de La Mer, baked with shrimp and seasoned crabmeat ($11).
Back in 1936 The same space served as the only library in Annapolis and surrounding Anne Arundel County for nearly 30 years.
Treaty of Paris
16 Church Circle, 410/216-6340
Located in the Maryland Inn (one of Annapolis' oldest hotels) near the city's historic waterfront, this cozy, subterranean eatery is a wonderful place to escape for a while and enjoy a quiet, leisurely lunch. Linger over a bowl of classic Maryland crab bisque (flavored with a touch of sherry; $7) and a fresh apple-and-cranberry salad ($7), before turning to the wine list, one of the state's best. White wine lovers may want to try a glass of Riesling from Willamette Valley Vineyards in Oregon ($9), while red fans should sample MacMurray Ranch's Pinot Noir ($12). Annapolis movers-and-shakers have been relaxing here since the 1700s, so whatever you order, you'll be in good company.
Back in 1783 It's rumored that John Jay, John Adams, and Benjamin Franklin came to the inn's former tavern not long after they signed the Treaty of Paris, which officially ended the Revolutionary War.
Carrol's Creek Cafe
410 Severn Avenue, carrolscreek.com
Come spring, the residents of America's Sailing Capital yearn to get out on the water (or at least be near it), and the deck of this Eastport eatery provides an ideal spot to watch the boats pull into the Annapolis City Marina. Catch a harbor breeze as you enjoy a bowl of Carrol's authentic cream of crab soup laced with sherry ($7.50), or the herb-crusted rockfish fillet served with pesto risotto and lump crab ($29).
Back in 1783 Before Baltimore was found to have a deeper harbor than Annapolis, the capital city was one of the busiest seafaring spots in the country. Annapolis even served as the nation's capital for an eight-month period from 1783 to 1784.
Annapolis Ice Cream Company
196 Main Street, annapolisicecream.com
This classic ice-cream shop garners praise for its fresh treats made on-site. The chilly menu offers seasonal flavors such as the springtime Blue Angel Blueberry (with berries and marshmallows). You can get the cool stuff in a bowl ($4) or order a family-filling ice-cream cake (8-inch cake for $22 or 10-inch version for $27).
Back in 1744 The first documented use in print of the term "ice cream" in the United States is found in a letter written by a dinner guest of Maryland Gov. Thomas Bladen in 1744.