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

Solo Travel on Maryland’s Eastern Shore: A Luxury Escape to Yourself

A Perfect Summer Day Trip to Rock Hall, Maryland

Scenic Byways Near Chestertown, MD: Slow Drives on Maryland’s Eastern Shore

Celebrate the Chestertown Tea Party Festival and Memorial Day Parade

Your Calendar of Chestertown, MD, Summer Events & Festivals

Slow Travel at Brampton 1860: Maryland’s Four-Season Sanctuary

Why a Workcation at Brampton 1860 Might Change Your Entire Year

Everything You Need to Know About Kayaking on Chester River, MD

Escape the City for a Romantic Getaway from NYC at Brampton 1860

How to Plan the Best Weekend Getaway from Washington, D.C.