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

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.

Chick & Ruth's Delly - 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/Scotlaur Inn
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Type:
Café


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


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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.

Maryland State House

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. 

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.

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 Road
Annapolis, MD 21401
410-757-1311


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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.

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.

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 Tavern-Annapolis
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Type:
American


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


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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.
Thomas Point Shoal Lighthouse in the Chesapeake Bay
Accessible only by boat, Thomas Point Shoal Lighthouse is one of only 10 in the country designated a National Historic Landmark.
Annapolis Spring Sailboat Show
Plan a visit around the Annapolis Spring Sailboat Show--you can even take a free sailboat ride!
Tour Annapolis Harbour
Tour Annapolis Harbour aboard the Queen Anne.

Annapolis

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Annapolis Events

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

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Annapolis Accommodations

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

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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 Attractions

Search our comprehensive list of attractions in Annapolis here.