10 Essential Things to Do in Annapolis

Annapolis, known as the “Sailing Capital of the U.S.,” is a city where history and maritime culture meet cosmopolitan charm. From the towering State House dome to the busy docks of Ego Alley, visiting Maryland’s capital is an immersive experience.

Here are 10 must-do activities for any visitor to Annapolis:

History & Government

1. Tour the Maryland State House: Step inside a piece of history. Built in 1772, the Maryland State House is the oldest state house still in use and once served as the nation’s capital. It was here that the Treaty of Paris was signed to end the Revolutionary War, and General George Washington resigned his military commission.
2. Tour the U.S. Naval Academy: Since 1845, the Academy has educated the officers of the U.S. Navy. The campus is steeped in military history, with highlights including the U.S. Naval Academy Museum and the domed chapel, which holds the ornate crypt of John Paul Jones, the father of the U.S. Navy.
3. Explore African-American History at the Banneker-Douglass Museum: The official African-American history museum of Maryland. It focuses on the legacies of celebrated figures like abolitionist Frederick Douglass and 18th-century scientist Benjamin Banneker.

Maritime & Water Experiences

4. Set Sail on the Schooner Woodwind for the Wednesday Night Sailboat Races: Every Wednesday from late April through August, over 100 yachts gather for the famous races. Join the crew of the schooners Woodwind and Woodwind II as they compete, placing passengers right in the thick of the action.
5. Join a Watermark Cruise or Walking Tour: Watermark immerses visitors in Annapolis’s history and culture both by land and water. Take a cruise to explore the Chesapeake Bay, or stroll through the charming streets with a colonial-attired guide on one of their popular walking tours.
6. “Flaunt It” on Ego Alley: A narrow waterway in the heart of historic downtown, Ego Alley is where boat owners cruise to show off their vessels. You can enjoy the spectacle from the shore or get a classic rum cocktail with dockside seating at Pusser’s Caribbean Grill.
7. Gaze at Yachts at the United States Sailboat Show: Sailors come from all over the world to experience this massive, largest and oldest in-water sailboat show on Earth, transforming the Annapolis Dock into a showplace for beautiful and exotic yachts.

Local Favorites & Entertainment

8. Dine on Crabs at Cantler’s Riverside Inn: Go off the beaten path to enjoy some of the best crabs and Maryland seafood around. Built over the water with a gorgeous view of quiet Mill Creek, Cantler’s is a can’t-miss spot where you can see the live tubs of crabs and fish fresh off the boats.
9. Have a Nosh at Chick & Ruth’s Delly: This has been an Annapolis institution since 1965, popular with midshipmen, governors, and tourists alike. Come early for a hearty breakfast and participate in the daily tradition of reciting the Pledge of Allegiance (8:30 AM weekdays, 9:30 AM weekends).
10. Hear Live Music at Rams Head On Stage: Rams Head is one of the best venues in the country to see national touring musicians across all genres. The intimate space ensures you never miss a note, with an extensive bar and in-show wait staff delivering food and beer right to your table.