Annapolis is consistently ranked one of America’s most walkable towns for good reason. This quaint, historic, waterfront town has changed little since its inception in the mid-17th century. 300-year-old buildings now play host to restaurants, pubs, specialty shops and boutiques, art galleries, music venues and so much more all within a small area making it easy to spend a day wandering around Annapolis.

Whether you’re in town for the day or making the most out of a weekend by staying downtown, walking around Annapolis is always a treat. 

The best way to spend a day walking Annapolis is to start on Main Street. The bustling business hub offers dozens of restaurant and shopping options. Starting at the top of Main Street and heading down the hill will bring you to City Dock, where you can grab a cup of coffee and relax on a bench overlooking the Annapolis Harbor as the boats cruise by. 

Walking the Dog on Main Street

Head back up the hill towards State Circle for a peek into the Maryland State House before heading down Maryland Avenue where more specialty shops line the brick streets. At the other end of Maryland Avenue (about three blocks down) is the United States Naval Academy. Open to the public (two forms of valid ID required), the Naval Academy is a great way to spend some time walking in Annapolis. Check out the word-class USNA Museum, or simply wander through the yard taking in all the beautiful architecture and history available on the grounds. 

All over Annapolis are hidden gems like the Hammond-Harwood House and the William Paca House and Gardens, where passersby can take a tour of these historic, 18th century homes. Head back up towards Church Circle and the Annapolis Arts District on West Street, where you’ll be treated to a handful of art galleries, and more restaurants.  

Just a short walk over the Spa Creek bridge in downtown lays the quiet neighborhood of Eastport. Here, you’ll find more art galleries, waterfront restaurants, and great views of downtown Annapolis.