Annapolis - The Best Things to Do

Annapolis is one of the oldest cities in America, but after checking out the Colonial architecture and dining on some variety of Chesapeake Blue Crab, what else is there to do? 

By Steve Carr - Owner of FREE! Annapolis Walking Tour

After taking the best tour in town with FREE! Annapolis Walking Tour, you will want to head over to the United States Naval Academy where you can easily spend a whole day roaming around the Beaux-Arts buildings and finely landscaped grounds.  Annapolis’ historic churches will entertain and delight you for several hours, as will the Annapolis State House, the oldest continually operating state house in America.  And all of these intriguing attractions are free.  But what can you do for some recreational fun?  Where can you go play?

SPA CREEK

Go Paddle-boarding or Kayaking  


Annapolis has two lovely creeks that are lined with marinas and attractive homes.  And there are several fine outfitters who rent small watercraft.  For those staying in downtown Annapolis without a car, your best bet would be Annapolis Canoe & Kayak on Spa Creek.    

And for Back Creek the best company is Capital SUP.  They even offer paddleboard yoga!  

     TRUXTON PARK

Go Sailing


Every street that ends on the water in Annapolis has a street-end park that’s free and which provides water access, including swimming.  Annapolis also has two large waterfront parks — Truxtun Park and Back Creek Nature Park — that are free and provide wooded hiking trails with spectacular water views.  Truxtun Park has an Olympic pool that is open to the public for a minimal fee in the warmer months. 

Annapolis is the sailboat capital of the world and everywhere you look there are sailboats large and small.  But how can you get out on the water and sail one?  There’s a great company called Schooner Woodwind Annapolis Sailing Cruises who operates out of the Annapolis Waterfront Hotel right downtown.  They have two historic log canoes outfitted with schooner rigs that are incredibly fast.  Take an unforgettable 2.5-hour sail with Captain Jen and her crew and you will even get a chance to take the helm as you cruise the waters of the Chesapeake Bay or the Severn River

AUTHOR STEERING WOODWIND #1 WITH WOODWIND #2 CLOSE BEHIND

Go Biking


Just outside Annapolis you will find the award-winning Baltimore and Annapolis Trail, a 13-mile asphalt trail on a former railroad line that runs all the way from Annapolis to Glen Burnie, just south of Baltimore.

This fun rail trail also connects directly to the scenic 12-mile BWI Loop Trail that winds around BWI/Thurgood Marshall International Airport.   

 AUTHOR BIKING ALONG THE CHESAPEAKE BAY

Explore A Local Park


And on the east side of Annapolis sits Quiets Waters Park, one of the region’s loveliest county parks, with miles of paved trails through the woods, a dog park, picnic pavilions and tables, a small boat rental, and outstanding views of the South River.  There is a $5 admission fee to enter the park by car.  

QUIET WATERS PARK 

Most visitors to Annapolis spend their entire time, walking around the historic downtown city center.  They check out the little shops on Main Street and Maryland Avenue, buy a goofy souvenir, eat at one of the seafood restaurants and sample a Maryland crab cake, hard crab, or soft crab, and walk around staring at the historic buildings and museums in between frequent stops for ice cream.  And while all those activities are interesting and enjoyable, there are many more fun things to do, most within a short distance of the Historic District.

OLD WOMAN'S COVE

So, I suggest you set aside at least five days for a visit to Colonial Annapolis, starting with the FREE! Annapolis Walking Tour, the best tour in town.  And then head for the water or a nearby local park, before riding one of the outstanding bike trails where you can get away from the crowds and enjoy the great Maryland outdoors.


Thank you for reading the article. For more travel tips from our local guides around the world check the blog section of our website! We release unique travel recommendations every week. If you like this article or have any question, feel free to leave us a comment below!

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