Fall in Annapolis. Locals know there’s nothing quite like it.

The season comes with a snap in the air and an energy that energizes the region—from the City Dock in downtown Annapolis to the fall festivals that stretch to the far corners of the Annapolis Countryside.

Some say summer is the best time to visit Annapolis—but in autumn, Annapolis offers visitors all the fun of summer without the heat.
The Chesapeake Bay plays host to those summertime activities like sailing and kayaking. The change in the air makes for a perfect walk down main street and a visit to the legendary United States Naval Academy.

Annapolis is known for its restaurants and summertime outdoor dining – whether on a rooftop patio, waterfront seating, or street-side table. Fall is the perfect time to take full advantage of the sunshine enjoying a meal before winter rolls into town. As is the case across Maryland, keeping a safe social distance, and wearing a mask helps you stay safe.

In October, the whole county is gearing up for seasonal events, tours, and festivals. Welcome to Fall in Annapolis. This month is one of the many reasons we love helping our clients find that perfect retreat. From waterfront homes on the Bay to downtown Annapolis, our client advisors are always a phone call away.