Setting: Chestertown sits 35 minutes northeast of the Chesapeake Bay Bridge (which connects the still-sleepy Eastern Shore to the rest of the state). Philadelphia, Baltimore, and Washington, D.C., all lie within a two-hour drive.
Attractions: The Chester River draws boaters, fishermen, kayakers, and birders.
Drawbacks: Young professionals face limited career opportunities. Beyond basics, shopping is limited. Many residents buy everything from gourmet foodstuffs to evening dresses via catalogs or the Internet.
Housing Options: Chestertown's architecture reflects its rich history. Outside the town limits, a handful of apartment complexes and suburban-style housing developments exist. Heron Point, a sprawling retirement community on the outskirts of town, attracts residents from all over the country.
What It Costs: The historic district, which encompasses downtown and beyond, almost to Washington College, offers a variety of options. Historic waterfront houses command premiums (Widehall, Chestertown's most elegant on-river mansion, sold for almost $3 million), but prices in the historic district start at $250,000. The area around Washington College offers good values in homes ranging from suburban tract styles to cozy bungalows (starting at $200,000) to charming Victorians (starting at $300,000).
Your Next-door Neighbors: Writers, artists, retirees, college professors (and students), doctors, boatbuilders, and hospitality-industry entrepreneurs.
How You'd Spend Your Free Time: Taking a cruise on the Sultana (410/778-5954 or schoonersultana.com). Walking along the newly restored riverfront. Riding a bicycle out to scenic Quaker Neck, which runs along the Chester River. Catching classic films (or live jazz performances) at the revitalized Prince Theatre. Taking a class at Washington College, which offers numerous open-to-all art, cultural, and political seminars and speakers, and has an excellent performing-arts curriculum.