So You Want to Live in ... Chestertown, Maryland

A lovely Maryland Eastern Shore village works toward a shipshape future.
By Carolyn Spencer Brown

When not roaming the Chesapeake Bay, Sultana, a gracious, two-masted sailing vessel, docks at its home port in the marina at the foot of Chestertown, Maryland. Sultana's builders and designers used historical documentation to painstakingly re-create the 18th-century schooner. This replica functions as both a pleasure-sailing craft for tourists and an educational tool for schoolkids.

Sultana represents far more than a deliciously recaptured slice of history. Chestertown, a charming Eastern Shore village on an arm of the bay, is home to 6,000 souls, bounded on one side by the Chester River and otherwise surrounded by farm fields and even smaller hamlets. Exquisitely restored Colonial homes line the brick-paved sidewalks and oak-shaded streets.

Beyond its placid demeanor, Chestertown proclaims itself "the town that beat Wal-Mart" for thwarting the discount retailer's plan to build a store there. After the victory celebration, resident Joyce Huber Smith said, "It's one thing to be anti-Wal-Mart―but what do we stand for?" Sultana's creation helped define Chestertown's aim, representing a commitment to preserve its past while focusing on its present.

Robert Mooney, author of the novel Father of the Man and a Washington College professor, says, "There is conviviality in town that's an interesting symmetry of a monied older generation and the college. These are two very strong and actively vibrant parts of the community." Ultimately, he adds, "Chestertown is like the way 'Cheers' used to sell itself―the town where everybody knows your name."

Native Anna Cole, proprietor of Scottie's Shoe Store (a combination footwear retailer, newsstand, and consignment shop) adds a different insight. "This is the friendliest town on earth," she says, "and it's due to a combination of folks: locals, who are down-to-earth and generous people, and folks who've escaped urban lifestyles for a slower pace and are grateful for it."

Whichever you are, she adds, "you never feel like a stranger."

(published 2004)