Get the inside scoop on life in Chestertown.

By Carolyn Spencer Brown
July 21, 2004
Get the inside scoop on life in Chestertown.

Setting: Chestertown sits 35 minutes northeast of theChesapeake Bay Bridge (which connects the still-sleepy EasternShore to the rest of the state). Philadelphia, Baltimore, andWashington, D.C., all lie within a two-hour drive.

Attractions: The Chester River draws boaters, fishermen,kayakers, and birders.

Drawbacks: Young professionals face limited careeropportunities. Beyond basics, shopping is limited. Many residentsbuy everything from gourmet foodstuffs to evening dresses viacatalogs or the Internet.

Housing Options: Chestertown's architecture reflects itsrich history. Outside the town limits, a handful of apartmentcomplexes and suburban-style housing developments exist. HeronPoint, a sprawling retirement community on the outskirts of town,attracts residents from all over the country.

What It Costs: The historic district, which encompassesdowntown and beyond, almost to Washington College, offers a varietyof options. Historic waterfront houses command premiums (Widehall,Chestertown's most elegant on-river mansion, sold for almost $3million), but prices in the historic district start at $250,000.The area around Washington College offers good values in homesranging 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, andhospitality-industry entrepreneurs.

How You'd Spend Your Free Time: Taking a cruise on the Sultana (410/778-5954 or Walking alongthe newly restored riverfront. Riding a bicycle out to scenicQuaker Neck, which runs along the Chester River. Catching classicfilms (or live jazz performances) at the revitalized PrinceTheatre. Taking a class at Washington College, which offersnumerous open-to-all art, cultural, and political seminars andspeakers, and has an excellent performing-arts curriculum.

(published 2004)