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

What Are the Best Things to Do Near Washington College?

Why You Need to See This Lavender Farm on the Eastern Shore of Maryland

All You Need to Know About the Chestertown, MD, Tea Party Festival and Memorial Day Parade

Why You Need to See a Show at The Mainstay in Rock Hall

Why This Spot Is the Best Irish Pub in Chestertown, Maryland

Fun in the Sun Awaits at the Best Summer Events in Chestertown, Maryland!

Satisfy Your Sweet Tooth at the Best Chestertown, Maryland, Bakeries!

Your Guide to the Best Hunting on the Eastern Shore of Maryland

What Are the Best Chestertown, Maryland, Theaters?

Your Complete Chestertown, Maryland, Holiday Gift Guide