A Weekend in Annapolis

Year-round adventure begins in Annapolis! From the shores of the Chesapeake to the excitement of Arundel Mills and everything in between, we are the ultimate weekend escape!

Just a stone's throw from Philadelphia, only 2.5 hours away by car, when you arrive in Annapolis, you can't help but be transported and charmed by the city's waterfront, live music, entertainment, and 18th-century architecture.

Everywhere you look, the city welcomes you with warm smiles, a thriving culinary scene, and nautical adventures. Perfect for a romantic weekend in a luxury bed and breakfast or a family escape in search of sailboats, crabs, and beaches! Stay close to Maryand's capital for music festivals, art shows, dining, and the United States Naval Academy.

Or stay just outside the city center and visit a brewery or winery, hike Sandy Point State Park, or press your luck at Live! Casino & Hotel.

Explore our guides to choose the perfect adventure, or download our 2024 visitor guide to plan your weekend in Annapolis and Anne Arundel County!


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Walkable Downtown Annapolis

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. 

Civil Rights Guide

2024 marks the 60th Anniversary of the signing of the Civil Rights Act. Explore the Annapolis and Anne Arundel County stories of the movement with a guide to 60 sites of historic importance in Anne Arundel County.

The Chesapeake Adventure

Experiencing the Chesapeake is all about getting your feet wet, tasting its flavors, and learning about its history. Here in Annapolis, the Chesapeake is on full display in all its glory.

Family Adventure

Family time is precious. There never seems to be enough of it! So, when you get together with loved ones, you want it to be special. Whether you’re traveling with toddlers, teenagers or ‘tweens, you can’t go wrong with Annapolis and Anne Arundel County! 

History Adventure

Are you a history buff? If so, you’ve come to the right place! As our nation’s first peacetime capital, you could say our nation took its first breath in Annapolis when the Treaty of Paris was ratified here – officially ending the Revolutionary War. And that's just the...


Getting to Annapolis, and then getting around while you're here is easier than you think. Browse the quicklinks below for more information.


Explore our Event Calendar

Discover arts and entertainment, culture, live music, and so much more on our events calendar, updated daily! For more inspiration, be sure to follow us on social @VisitAnnapolis