Chestertown Historic District: A Walking Guide to Three Centuries of Architecture

Most of what people mean by “old town Chestertown” is technically the Chestertown Historic District, a National Historic Landmark on the Chester River that’s been on the National Register of Historic Places since 1970. The original district covers much of the historic core near the Chester River, Cannon and Cross Streets, and Maple Avenue, with […]

Things to Do in Chestertown, MD: The Complete Guide

Chestertown sits on the Chester River about twenty minutes from our front door, and with so many things to do in Chestertown, MD, it’s the perfect day trip. Founded in 1706 as an important colonial port of entry, it’s held onto its brick sidewalks and Georgian architecture in a way that few Chesapeake towns have, […]

Fantastic Chestertown, MD Restaurants on the Eastern Shore

We already know (and celebrate) the many fantastic restaurants in Rock Hall, MD. They do a remarkable job of showcasing the rich seafaring history of this region. But just as magnificent as the town of Rock Hall is our neighboring community of Chestertown, where you’ll find another welcome array of Chestertown, MD restaurants to enjoy. […]