Uploaded May 2016 | Updated September 2026, 1 week ago
The Chester River is one of the quintessential tributaries of the Chesapeake Bay. Rich in history and fairly unchanged from past centuries, the river links two of the best towns the Eastern Shore has to offer: Centreville and Chestertown. With colonial architecture lining the streets, it is easy to imagine life during the booming era of tobacco. Today these towns continue to thrive through their gourmet restaurants, charming boutiques, street festivals and a variety of outdoor activities offered year-round. Shop at the popular farmers markets open early spring through October, which offer produce, meats, wines and bakery fresh items that only the fertile Eastern Shore has to offer. Take a sunset cruise on the Chester River Packet, a 1920’s style river boat. Watch a log canoe regatta; a unique type of classic sailboat that can only be found on the Eastern Shore. Tour vineyards, go fishing for rockfish, eat oysters and blue crabs dusted in Old Bay with super sweet and local corn-on-thecob, watch herons and ospreys fish along the water’s edge and admire the sprawling green fields and forests that span the river. Nowhere else can you enjoy the quiet, less-inhabited beauty of life on the water while still being an easy commute to D.C., Baltimore and Annapolis.
The Chester River is one of the quintessential tributaries of the Chesapeake Bay. Rich in history and fairly unchanged from past centuries, the river links two of the best towns the Eastern Shore has to offer: Centreville and Chestertown. With colonial architecture lining the streets, it is easy to imagine life during the booming era of tobacco. Today these towns continue to thrive through their gourmet restaurants, charming boutiques, street festivals and a variety of outdoor activities offered year-round. Shop at the popular farmers markets open early spring through October, which offer produce, meats, wines and bakery fresh items that only the fertile Eastern Shore has to offer. Take a sunset cruise on the Chester River Packet, a 1920’s style river boat. Watch a log canoe regatta; a unique type of classic sailboat that can only be found on the Eastern Shore. Tour vineyards, go fishing for rockfish, eat oysters and blue crabs dusted in Old Bay with super sweet and local corn-on-thecob, watch herons and ospreys fish along the water’s edge and admire the sprawling green fields and forests that span the river. Nowhere else can you enjoy the quiet, less-inhabited beauty of life on the water while still being an easy commute to D.C., Baltimore and Annapolis.
