Maryland Eastern Shore Blog | Events and Activities in Chestertown

Couple toasting glasses of champagne outside

Sun setting over a lake with ducks floating on the water

Seating area for two in the Emory Suite at Brampton Inn

Couple enjoying a romantic picnic outdoors

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

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

We Adore the Most Romantic Things to Do in Annapolis, Maryland!

The Chestertown, Maryland, Farmers Market Is the Best Local Attraction!

Here Are the Top Festivals and Events to Attend in Chestertown, MD!