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

Christmas in Maryland: A Storybook Holiday on the Eastern Shore

Proposals at Brampton 1860 – The Perfect Place to Pop the Question

Rent the Entire Brampton 1860 in Chestertown, MD

Your Perfect Midweek Getaway on Maryland’s Eastern Shore

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

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

A Wellness Getaway in Maryland That Actually Helps You Slow Down

Why a Workcation at Brampton 1860 Might Change Your Entire Year

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

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