Annapolis, the capital of Maryland, makes for a fantastic long weekend family escape or a great day trip if you’re visiting nearby D.C.. Located at the heart of Chesapeake Bay, America’s Sailing Capital has been a bustling port town since the 18th century and is home to the U.S. Naval Academy and restaurants featuring the absolute freshest catches of the day. With more 18th-century buildings than anywhere else in the nation, picturesque brick-lined streets and historic sites galore, Annapolis is a museum without walls that invites families to learn and explore.
George Washington came before Congress at the Maryland State House to resign his commission as commander-in-chief of the Continental Army. The Treaty of Paris was ratified here, too, marking the official end of the Revolutionary War. Entry is free.
The U.S. Naval Academy is the training ground for officers in the U.S. Navy and Marine Corps. Its impressive museum holds more than 5,000 artifacts and showcases the history of seapower and the development of the U.S. Navy. Be sure to check out the Rogers Ship Model Collection, which includes 108 ship and boat models of the sailing ship era dating from 1650 to 1850.
A boat departs from the Maritime Museum, twice monthly from July-October, taking visitors to the Thomas Point Shoal Lighthouse. Built in 1875, this beautiful lighthouse is the last screwpile lighthouse on the Bay still in its original location, one-and-a-half miles offshore in the Chesapeake Bay at the mouth of the South River.
Quick and affordable, water taxis are a fun way to get around Annapolis. Hop on a water taxi at the City Dock and chug on over to Eastport for lunch: Boatyard Bar and Grill (400 4th St.) has delicious crabcakes and comfy outdoor seating.
Step into the Annapolis Ice Cream Company (196 Main Street) for a scoop of 17% butterfat, house-made ice cream. Voted “Best in Annapolis” for 8 consecutive years, the rotating menu of flavors always delights. Grab some markers and decorate a spoon that will be kept on the wall as a souvenir of your visit.
Start your day with the Pledge of Allegiance at Chick & Ruth’s Delly. Owner Ted Levitt invites visitors to join him in reciting the pledge every weekday morning at 8:30 a.m. and weekends at 9:30 a.m.. Afterwards, grab a straw for every member of you family and enjoy a giant milkshake, dubbed the largest milkshake in the world, and a Super Duper Colossal Burger, which weighs in at 3 pounds.
Located next to the Barry entrance of the U.S. Naval Academy, Gibson’s Lodgings (110 Prince George St.) is a historic inn with modern amenities. 20 fully-furnished guest rooms, with three 19th-century parlors, a dining room, conference room, and a lovely central courtyard will give your family space and a comfy and affordable place to rest after the end of a busy day exploring Annapolis.