Historical trip to Annapolis: What to do in the Maryland capital

To visit the nation’s capital from New York, you have to travel through Maryland. But 30 miles east of Washington, D.C., sits Maryland’s capital — and the nation’s former capital — Annapolis.

The city of about 40,000 is easy to miss amid the D.C.-Baltimore metro area but worth a detour. Naptown is famously home to a district of Colonial-era homes, the oldest state capitol in continuous use, fantastic crabcakes and, of course, the United States Naval Academy.


Annapolis is best seen by foot. Fill up on carbs at Chick & Ruth’s Delly (165 Main St., 410-269-6737, chickandruths.com). This greasy spoon has been a mainstay on Main Street since the mid-1960s, and, being a short walk away from the state house, has served generations of politicians and hungry visitors alike. Finish off your meal with a slice of one of 26 pies.


Embark on a history walking tour starting at the Maryland State House (100 State Circle, msa.maryland.gov), which served as the home of the Second Continental Congress and nation’s capital for nearly a year in the 1780s. Don’t miss the memorials to Matthew Henson, the first man to step foot on the North Pole, and Thurgood Marshall, the first African-American Supreme Court justice.

A walk down Main Street will take you down to Annapolis harbor. Get some ice cream, check out the boats and see the statue of “Roots” author Alex Haley. Steps away is Middleton Tavern (2 Market Space, 410-263-3323, middletontavern.com); opened in 1750, it’s a great spot to lunch or drink in the footsteps of famous visitors such as George Washington and Benjamin Franklin.

From there, it’s time to see more Colonial-era history with a tour at nearby 18th-century homes, including the Chase-Lloyd House (admission $5; 22 Maryland Ave., chaselloydhouse.org), the Charles Carroll House (107 Duke of Gloucester St., charlescarrollhouse.org), and the William Paca House and Garden (from $5; 186 Prince George St., annapolis.org), which all were former homes of signers of the Declaration of Independence.


The sheer size of the U.S. Naval Academy makes it impossible to miss, and you will definitely run into a midshipmen or 10 in town. The 338-acre complex, home to about 4,400 midshipmen, is free to tour (entrance at Gate 1 off Prince George Street, 410-293-8687, usnabsd.com/for-visitors). Guided tours are also available through the visitor’s center to see sites such as the Statue of Tecumseh, Naval Academy Museum and the crypt of Revolutionary War naval hero John Paul Jones.


Keeping the midshipmen entertained means that downtown Annapolis has plenty of bars and restaurants. Dives, wine bars and Irish bars are plentiful along Main Street, and most serve fantastic seafood.

A short walk, or quick cab ride, to the Eastport area is O’Leary’s Seafood (310 Third St., 410-263-0884, olearysseafood.com) and Carrol’s Creek Cafe (410 Severn Ave., 410-263-8102, carrolscreek.com). For carnivores, you can’t go wrong with Lewnes Steakhouse (410 Fourth St., 410-263-1617, lewnessteakhouse.com).

Back across the bridge downtown, whet your whistle back at Stan & Joe’s (37 West St., 410-263-1993, stanandjoessaloon.com) for cold beers and live music, the Rams Head Tavern (33 West St., 410-268-4545, ramsheadtavern.com) for more nationally well-known acts, or the Chesapeake Brewing Co. (114 West St., 410-268-0000, chesbrewco.com) for local craft brews.


Conveniently across the street from Chesapeake is the Loews Annapolis (126 West St., 410-263-7777, loewshotels.com), a polished new spot with a trendy hotel bar. The Annapolis Waterfront Hotel (80 Compromise St., 800-393-0047, annapoliswaterfront.com) comes with great harbor views and Pusser’s Caribbean Grille on-site. For something more historic, there are dozens of bed and breakfasts in old homes, or the Maryland Inn (16 Church Circle, 410-263-2641, historicinnsofannapolis.com), an 18th-century building-turned-hotel.