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'Rockwell would have plenty to paint'
 | | ArtToday.com | | A fountain graces the town square in Chestertown. |
In Chestertown, “Norman Rockwell would have plenty to paint,” a journalist once wrote of this small town 47 miles northeast of Annapolis in Kent County, “and Sinclair Lewis would be busy taking notes.”
The small Kent County town, 47 miles northeast of Annapolis, is the kind of place where the downtown shops have the names of their owners – not those of national chains – on the signs out front. Residents gather in the town square each December to sing carols around a Christmas tree. And the townsfolk celebrate the Chestertown Tea Party every May, commemorating the 1774 event when local patriots tossed British tea in the Chester River.
The centerpiece of the festival, which boasts pipe bands, dancers, musicians, fabulous food, and crafts, is a reenactment of the revolutionary protest in which colonials threw tea into the Chester River. Tea parties of another sort can be found more frequently – every afternoon – at the White Swan tavern on High Street, a restored 18th century inn with Colonial-period antiques, such as a grandfather clock and an early 1700s writing desk.
From the manicured gardens of the grand old homes along the Chester River to the antiques-filled rooms of local inns to the beloved Geddes-Piper House, a Federal-style historic home, Chestertown places a premium on preservation.
The town is home to Washington College, the only one that George Washington allowed to use his name. (He served as a trustee and received an honorary degree). Like generations of students before them, the nearly 1,000 undergraduates live and attend classes in colonial-style brick buildings that line a quad on Washington Avenue. The nation’s 10th-oldest college, founded in 1782, boasts a nationally recognized undergraduate writing program.
The Geddes-Piper House, too, offers a glimpse of Chestertown’s colonial past. The museum displays 18th-century furnishings, clothing and cookware in a 1784 townhouse that houses the Historical Society of Kent County. And maritime history comes alive in Chestertown thanks to the Sultana, a reproduction of a
 | | ArtToday.com | | Historic homes line wide brick pavements. |
1768 ship built by local volunteers that is docked at the end of Cannon Street.
But visitors will find more than a history lesson here. Today, inns, restaurants, antique shops and cozy cafes line the wide, brick pavements of High Street, but Chestertown retains its small-town feel. The population hasn’t grown for a century, though several excellent restaurants have opened in recent years to cater to the tourists and newer residents.
Splendid brick mansions grace the shores of the expansive Chester River, while churches, historic homes, squares, parks, monuments, shops, inns and restaurants line the downtown streets.
Locals and visitors alike gravitate to the town square, with a picturesque working fountain and a clock tower illuminated at night
The town traces its roots to 1706 but gained prominence in Colonial America when it was named one of the Maryland colony’s six Royal Ports of Entry. By the mid-18th century, Chestertown trailed only Annapolis as Maryland’s leading port.
Whether visitors want a quiet getaway in one of the inns or bed and breakfasts in restored inns or historic manor homes, an active few days of biking, boating and kayaking on the Chester River or a relaxed stroll through the antique shops, Chestertown has a way of making visitors feel right at home.
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