Maryland Eastern Shore Blog | Events and Activities in Chestertown

couple on a walking trail

Sun setting over a lake with ducks floating on the water

Two navy and white paisley chairs in a cozy carpeted room with window and TV

Couple enjoying a romantic picnic outdoors

Catch a glimpse of a Blue Heron while bird watching near Chesapeake Bay

Best Places to Eat Crab In and Around Chestertown, MD

Your Guide to the Best Golf Courses on the Eastern Shore of Maryland

Picture Perfect Elopements and Small Weddings in Maryland

Another pet friendly cottage at our Chestertown Inn

Arts & Entertainment District :: Chestertown, MD Events

The 6 Best Places to See Fall Foliage in Maryland

Proud to be a Member of Select Registry

Sultana Downrigging Weekend in Chestertown, MD: What You Need to Know

A little history lesson…