Located in the former steamboat port of Irvington, The Hope and Glory Inn's accomodations comprise seven rooms in an 1890 schoolhouse, plus 6 cottages. Although it doesn't overlook water, its owners host weekend crab-and-cocktail cruises aboard their 1952 Chesapeak Bay workboat, The Faded Glory; 800/497-8228.
Eat: Stop by The Local for a coffee and breakfast sandwich, or grab a wrap or salad at lunchtime. The Trick Dog Cafe is a sophisticated but playful dinner spot where you can expect wine-braised lamb shanks or crab cakes.
Do: Trendy shops abound in Irvington. Stop by The Dandelion for clothing, jewelry, and housewares, or The River Cottage to peruse its hodgepodge of merchandise. Get a glimpse into the vessels that helped shape cities and towns along the Chesapeake at The Steamboat Era Museum.