Annapolis, MD downtown street

2021 Top 100 Best Places to Live In America Sponsored by: See homes for sale on Movoto by OJO

liv score
How We Calculate Our Data
Civics 76
Demographics 68
Economy 52
Education 53
Health 42
Housing 52
Infrastructure 41

#38. Annapolis, MD

Maryland’s capital city sits on the edge of the picturesque Chesapeake Bay, which provides a scenic backdrop to this colonial city. The most widely known site in the historic district is the U.S. Naval Academy, but Annapolis, MD also has more original 18th-century buildings than any other American city. In addition to its historical presence, Annapolis is home to a vibrant sailing community — sailboats and yachts fill the bay. The city hosts several boating competitions throughout the year and restaurants boast freshly caught oysters, crab and shrimp on their sidewalk menus.  

Top Colleges/Universities: United States Naval Academy 

Top Industries & Employers: Annapolis‘ top employers are accommodation and food services, professional, scientific and technical services and public administration. 

Weekend Plans: Sail the Annapolis Harbor and learn the history of the Naval Academy aboard the 40-minute narrated Harbor Queen cruise. 

Favorite Place to Feast: In addition to serving the best crab cakes on the Eastern seaboard, Chick and Ruth’s serves a hearty breakfast. Stop by this Annapolis institution to take part in the daily recital of the Pledge of Allegiance every weekday morning at 8:30. 

Beloved Beverage: Pusser’s Caribbean Grille is the only bar outside the British Virgin Islands that makes the rum, coconut, pineapple cocktail called the Pusser’s Painkiller. It is the unofficial cocktail of Annapolis‘ annual United States Sailboat and Powerboat Show. 

Outdoorsy Activity: The almost 800-acre Sandy Point State Park located along the Chesapeake Bay is best known for its swimming beaches, fishing spots and wildlife viewing. 

Rooftop Bar: Nosh on a locally sourced charcuterie board while gazing out over the city at the Metropolitan Kitchen and Lounge.

Why Your Pet Will Love It, Too: In addition to extensive hiking, biking and walking trails, Quiet Waters Park has two fenced-in dog parks as well as a dedicated dog beach. 

Remote Work Perk: Annapolis is one of the oldest cities in America. When it is time to take a break from the computer, take a stroll around the historic center where a National Historic Landmark sits around every corner. 

One More Thing … Annapolis was home to the Continental Congress for two years following the Revolutionary War, making it the first capital of the United States of America. 

– Brittany Anas

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