Notes from My Chesapeake Home

Sharing local stories, market trends, and real estate advice for buyers and sellers across Maryland’s Eastern Shore.

My Eastern Shore Fall Bucket List

Fall might be my favorite season on the Shore. Here’s my personal bucket list, from oyster spots and apple orchards to festivals, scenic trails, and cozy nights out, with dates to mark on your calendar this year.

Things to Do in Chestertown, MD This Spring

Things to Do in Chestertown, MD This Spring

Spring is one of the best times to experience Chestertown, MD. From waterfront walks along the Chester River to farmers markets, local dining, historic streets, and signature seasonal events, this guide highlights the best ways to enjoy Chestertown this spring.

An aerial view of downtown Chestertown

Spring in Kent County: A Curated Guide to the Eastern Shore Lifestyle

Spring in Kent County offers one of the clearest glimpses into what makes Maryland’s Eastern Shore so appealing. From Chestertown’s historic charm and community events to Rock Hall’s waterfront energy, this guide explores the places, experiences, and local lifestyle that make spring such a beautiful time to discover the Shore.

View of the Chesapeake Bay Bridge from the beach on the Eastern Shore

Living on Kent Island: What Bay Bridge Access Really Means for Homebuyers

For many buyers considering the Kent Island area, one factor consistently rises to the top: access to the Chesapeake Bay Bridge. While Kent Island offers waterfront living, marinas, and established neighborhoods, its proximity to Annapolis, Baltimore, and Washington, DC makes it uniquely positioned among Eastern Shore communities. But what does “close to the bridge” actually mean in daily life?

Up close of a couple holding hands in winter coats

A Couples’ Guide to Winter in Kent County, Maryland

Looking for a cozy winter escape with your favorite person? Discover Kent County’s most romantic spots: from fireside dinners to peaceful waterfront strolls. Whether it’s a weekend getaway or a peek into future retirement, this guide is your invitation to slow down and savor the season together.