Spend a calm evening watching the Wednesday Night Sailboat Races in Annapolis MD.
Wednesday Night Sailing Races in Annapolis
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10 Things to Do in Annapolis

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.

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Noon Formation at U.S. Naval Academy - Annapolis Photo By: Visit Annapolis

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.


More about U.S. Naval Academy-Armel-Leftwich Visitor Center
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Type:
Tour Services


Location:
52 King George Street
Annapolis, MD 21402
410-293-8687


Chick & Ruth's Delly - Annapolis Photo By: Visit Annapolis

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
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Type:
American


Location:
165 Main St
Annapolis, MD 21401
410-269-6737


Cruise up in your boat to Ego Alley, or come on foot and marvel at the beautiful boats.

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. 

U.S. Sailboat Show - Annapolis

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.


More about United States Sailboat Show
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Type:
Events


Location:
One Dock St
Annapolis, MD 21401
410-268-8828


Maryland State House Photo By: Visit Annapolis

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. 


More about Maryland State House
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Type:
History & Heritage


Location:
100 State Cir
Annapolis, MD 21401


Spend a calm evening watching the Wednesday Night Sailboat Races in Annapolis MD.

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.


More about Wednesday Night Sailboat Races
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Type:
Events


Location:
2 Compromise Street Annapolis
Annapolis, MD 21401
410-263-9279


Cantlers Riverside Inn Photo By: Cantlers Riverside Inn

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
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Type:
Seafood


Location:
458 Forest Beach Rd
Annapolis, MD 21401
410-757-1311


Blue Angels, the U.S. Navy Flight Demonstration Squad.

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.


More about U.S. Naval Academy
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Type:
Attraction


Location:
Armel-Leftwich Visitor Center
Annapolis, MD 21402
410-293-8687


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

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.


More about Banneker-Douglass Museum
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Type:
Visual Arts


Location:
84 Franklin St
Annapolis, MD 21401
410-216-6180


Rams Head on Stage

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 on Stage-Annapolis
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Type:
Live Music


Location:
33 West St
Annapolis, MD 21401
410-268-4545


Annapolis Photos & Videos

Ego Alley in Annapolis
Cruise up in your boat to Ego Alley, or come on foot and marvel at the beautiful boats.
Wednesday Night Sailing Races in Annapolis
Spend a calm evening watching the Wednesday Night Sailboat Races in Annapolis MD.
Sunrise at Sandy Point State Park
Enjoy the amazing sunrises on Maryland's coast from Sandy Point State Park.
Photo By: Maryland Office of Tourism
Accessible only by boat, Thomas Point Shoal Lighthouse is one of only 10 in the US designated a National Historic Landmark.
Accessible only by boat, Thomas Point Shoal Lighthouse is one of only 10 in the country designated a National Historic Landmark.
Annapolis Sailboat Show
Plan a visit around the Annapolis Spring Sailboat Show--you can even take a free sailboat ride!
Photo By: Annapolis Tourism
Tour Annapolis Harbour aboard the Queen Anne.
Tour Annapolis Harbour aboard the Queen Anne.
Photo By: Visit Annapolis

Annapolis

Trip Ideas

Spend a calm evening watching the Wednesday Night Sailboat Races in Annapolis MD.
10 Things to Do in Annapolis

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!

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Annapolis Arts and Crafts Festival
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Search for events in Annapolis and plan your trip around popular events like the First Sunday Arts Festival, Annapolis Film Festival and the St. Patrick's Day Parade.

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Discover the wide variety of charming places to stay in Annapolis with this list of hotels, motels, B&Bs.

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Search our comprehensive list of attractions in Annapolis here.
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