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

Your Ultimate Guide to the Best Fall Hikes in Maryland

Why Chestertown Is One of the Best Winter Getaways From D.C.

The Ultimate Thanksgiving Getaway to Chestertown Maryland

We Know One of the Best Weekend Trips from Baltimore In Winter

Here Is the Ultimate Itinerary for 3 Nights in Chestertown, MD

5 of the Best Things to Do in Rock Hall, MD

What Is the Best Chesapeake Bay Boat Tour?

Why You Need to Take a Cruise on the Chester River Packet!

Why Chestertown Is One Of The Best Eastern Shore Of Maryland Historic Towns

Have Fun in the Sun at the Best Beaches Near Chestertown, MD