Annapolis Harbor
Visit Annapolis

10 Things to Do in Annapolis

By Jim Meyer

From the soaring statehouse dome on down the old bricked main street to the mega-yachts of Ego Alley, visiting Annapolis is a capital idea!

Annapolis Harbor
Visit Annapolis

Known as the "Sailing Capital of the U.S." and home to the U.S. Naval Academy

Annapolis's maritime heritage combined with its cosmopolitan flair create a destination unlike any other. Explore the sites via water or land with boat and walking tours. Don't miss the Annapolis Oyster Roast & Sock Burning. A tradition each March 21st since 1978, guests come out of hibernation to burn their old winter socks and ceremoniously welcome spring with live music, oysters, libations and a whole lot of barefoot fun! 

Tour the U.S. Naval Academy
Noon Formation at U.S. Naval Academy - Annapolis
Visit Annapolis

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. The Blue Angels—the U.S. Navy’s famous fighter jet demonstration team performs a fly-over and airshow at every graduation.

Have a Nosh at Chick & Ruth's Delly
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).

If You've Got It, Flaunt It on Ego Alley
Cruise up in your boat to Ego Alley, or come on foot and marvel at the beautiful boats.

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 Pusser's Caribbean Grill. With dockside seating right on Ego Alley, it’s prime real estate for taking in the yachts. 

Gaze at yachts at the United States Sailboat Show
U.S. Sailboat Show - Annapolis

Sailors come from all over the world to experience the largest and oldest in-water sailboat show on Earth. The Annapolis Dock becomes a showplace for the most beautiful and exotic boats in the world, and they’re worth seeing whether you’re shopping or just dreaming.

Tour the Maryland State House
Maryland State House
Visit Annapolis

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. 

Set Sail on the Schooner Woodwind for the Wednesday Night Sailboat Races
Schooners Woodwind and Woodwind II racing each other during the Wednesday Night Races.
Schooner Woodwind Annapolis Sailing Cruises

More than 100 yachts gather every week from late April through August for the famous Wednesday Night Races, and there's no better spot for race night than the decks of schooners Woodwind and Woodwind II. The two boats put passengers to work as they compete in a class all their own. Since this regular event happens in the "Sailing Capital of the World," the vessels are fast and the competition is fierce, and the Woodwind crews keep you in the thick of the race and up to speed on the action! With your help, your boat might even win the race!

Dine on Crabs at Cantler's Riverside Inn
Cantler's 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, Cantler's is a can’t-miss! Check out the live tubs out back—they’re often full of crabs and fish fresh off the boats.  Or check out the entire area's selection at our Annapolis and surrounding area Crab & Oyster Trail.

Join a Watermark Cruise or Walking Tour

Watermark offers so many ways to immerses visitors in the history, culture, and fun of Annapolis, both by land and by water. History comes alive when you stroll through the charming streets of Annapolis with a colonial attired guide on any one of Watermark's fascinating walking tours. Or explore the Chesapeake Bay from Annapolis on an unforgettable journey on a  Watermark cruise or yacht charter. Be sure to take advantage of the Annapolis Water Taxi for touring the Annapolis Harbor.

Explore African-American History at the Banneker-Douglass-Tubman Museum
Visit the Banneker Douglass Museum of African American history and cultur for special exhibits, lectures, films, tours and educational programs about African-American History.

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.

Hear Live Music at Rams Head On Stage
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.