8 Prettiest Main Streetscapes In Chesapeake Bay

Small towns along the Chesapeake Bay don't stray far from the shoreline. These ones in particular, split between Maryland and Virginia, are built around a main street that showcases the region's maritime heritage and prioritizes access to water. Here, you can wander Chestertown's High Street, where old brick sidewalks lead down toward the river. Talbot Street runs north through Saint Michaels to the Chesapeake Bay Maritime Museum and its 1879 Hooper Strait Lighthouse. The Victorian facades along Mason Avenue in Cape Charles end at the beachfront and the fishing pier. These eight communities have the prettiest main streetscapes on the Chesapeake Bay, best explored on foot at a leisurely pace.