10/19/2026
Welcome to Shady Side Part Two: There’s a lot of history packed into this little peninsula.
Shady Side, MD has generations of watermen, historically Black waterfront communities, old Chesapeake families, and places like the Captain Avery Museum that help tell the story of the people who have called this place home.
It’s that history that gives Shady Side its sense of place — and why it feels so different from anywhere else.
Do you have a connection to Shady Side? I’d love to hear your story — tell me about it in the comments. And follow along for more stories about the places that make Maryland special.