Life in Chestertown

Get the inside scoop on life in Chestertown.

Chestertown, Maryland

 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.

(published 2004)

    1 of 1

    Most Popular

    1. 20 Beautiful Beach Cottages

      From polished and sophisticated to rustic and casual, browse through this roundup of beach cottages to find your favorite coastal style.
    2. 29 Delicious Salads
    3. Top 21 Beaches, Coast to Coast
    4. Go Pastel for Spring!
    5. 100 Comfy Cottage Rooms