Top Things to Do in Annapolis
This “Sailing Capital of the World” is truly the crown jewel of the Chesapeake Bay. Known for the elite U.S. Naval Academy, the United States Sailboat Show, and its historic Maryland State House, Annapolis is also home to charming, bricked streets lined with one-of-a-kind shops and restaurants. The state's Capital is one of the most walkable cities in the country and consistently named one of the top ten places in America to live. Come visit and see why.
1 Tour the U.S. Naval Academy
Since 1845, the Academy has been educating the officers of the United States Navy, and the Academy campus is steeped in that history and culture. Highlights include the United States Naval Academy Museum and the beautiful domed chapel that holds the ornate crypt of John Paul Jones, father of the U.S. Navy.
2 Have a Nosh at Chick & Ruth's Delly
Since opening its doors on Main Street in 1965, Chick & Ruth’s Delly has been a favorite for midshipmen, governors, locals and tourists alike—it’s an Annapolis institution. Come early to enjoy a hearty breakfast and take part in the daily Pledge of Allegiance, recited every morning –it’s a Chick & Ruth’s tradition (8:30 AM on weekdays, 9:30 AM on weekends).
More about Chick & Ruth's Delly
165 Main St
Annapolis, MD 21401
3 If You've Got It, Flaunt It on Ego Alley
If you’ve got a boat to show off, cruise to Ego Alley, a narrow waterway in the heart of historic downtown Annapolis. Once you arrive, or if you’re just there to watch, stop in for a bite and a classic rum cocktail at Pussers’ Caribbean Grill. With dockside seating right on Ego Alley, it’s prime real estate for taking in the yachts.
4 United States Sailboat Show
Sailors come from all over the world to experience the largest and oldest in-water sailboat show on Earth. The miles of Annapolis Dock become a showplace for the most beautiful and exotic boats in the world, and they’re worth seeing whether you’re shopping or just dreaming.
5 Tour the Maryland State House
Touring these halls is like taking a walk through history. Older than the country itself, the Maryland State House was built in 1772 and is the oldest state house still in use. Once the capital of the nation, it was here that the Treaty of Paris was signed to end the Revolutionary War, and General George Washington resigned from his post as commander of the Continental Army.
6 Watch the Wednesday Night Sailboat Races
More than 100 yachts gather every Wednesday night from late April through August for the famous Wednesday Night Races. Spectators follow along in boats, gather on the downtown Spa Creek Drawbridge, or watch from waterfront restaurants and watering holes. Since this regular event happens in the “Sailing Capital of the World,” the boats are fast and the competition is fierce.
7 Dine on Crabs at Cantlers Riverside Inn
Go a bit 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, Cantlers is a can’t-miss! Check out the live tubs out back—they’re often full of crabs and fish fresh off the boats.
More about Cantler's Riverside Inn
458 Forest Beach Road
Annapolis, MD 21401
8 See the Blue Angels
Graduation at the U.S. Naval Academy means white-suited midshipmen and the jubilant hat throw. While all schools like to show off for graduation, the U.S. Naval Academy takes it to another level (literally!) with the Blue Angels—the U.S. Navy’s famous fighter jet demonstration team performs a fly-over and airshow at every graduation.
9 Explore African American History at the Banneker-Douglass Museum
The official African American history museum of Maryland focuses on two celebrated figures in American history: Frederick Douglass, the great writer and abolitionist, and Benjamin Banneker, the 18th-century mathematician, astronomer and author whose work inspired many in the drive for freedom.
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 keeps the audience close to performers so you never have to miss a note. There’s an extensive bar, and the in-show wait staff delivers the pub’s fantastic food and beer right to your table.
More about Rams Head Tavern-Annapolis
33 West St
Annapolis, MD 21401