Chestertown native Shelley Lepter remembers being underwhelmed on her first trip to Colonial Williamsburg in Virginia.
"I thought, well, they've re-created all this stuff. In Chestertown, we've got the real thing," says Mrs. Lepter, who now lives on the Chester River a few miles out of town.
Chestertown, a charming town on the banks of the Chester River, does indeed have the real thing, from historic Washington College -- the 10th oldest university in the nation -- to Georgian mansions along the river to Colonial taverns and churches established in the late 1700s.
Founded in 1706, the Kent County town has a lively, historic downtown district that's an interesting mix of government offices, residences, restaurants and shops.
"It looks like a miniature Williamsburg, except people have always lived in these homes," says Pat Piposzar, executive director of the Kent County Chamber of Commerce, which has offices in Chestertown. "It's a living, working Colonial town."
Carla Massoni, co-owner of the Massoni-Sommer art gallery, says Chestertown is an interesting mix of people, businesses, styles and trades, which is what separates it from many other small towns.
"What a lot of people are attracted to is the full range of people, the breadth of the community. This is a working town, it's not just a tourist attraction," says Ms. Massoni, who moved to Chestertown from Chevy Chase in 1989 and also co-owns the Imperial Hotel in the center of the historic district.
"There's many artists and writers who live here, and there's farmers and watermen. Because of the college, there's a strong intellectual middle class here."
Many townsfolk say Washington College, a prestigious liberal arts college in the center of town, is largely what sets Chestertown apart from other Eastern Shore towns.
In addition to being the third largest employer in town, the college attracts talented students, scholars and professors and a variety of visiting lecturers.
Dr. John S. Toll, former chancellor of the University of Maryland System, took the reins of the college in January as acting president and will be sworn in as its president in September. He has enjoyed his transition from huge, state university to small, independent college with an enrollment of 850.
"This is a college that focuses on the arts and sciences and does a very good job helping every student learn," he says. "The townspeople come and take classes here. They go to lectures, to the symphony. It's just an ideal atmosphere for a college."
Chestertown is also the county seat and home of Kent & Queen Anne's Hospital, which provide numerous jobs and add to the mix of people living and working here.
"We have the charm of a small town and the security of a small town," says Mayor Margo Bailey. "But we've also got great sophistication here, along with the country life."
Chestertown has an unmistakable small-town feel, from its walkable scale to its friendly residents, who know each other by name. The year-round population -- 4,005 according to the 1990 Census -- has remained fairly stable for decades, residents say, although there are more people in town when boaters, summer residents and day-trippers start arriving in early spring.
Meredith Davies Hadaway, director of college relations at Washington College, moved to Chestertown just out of college, not for a job but for that small-town experience.
"I grew up moving a lot; my father was in the Navy and I went to school is Washington," she says. "I used to visit here because I had friends at Washington College, and I was just smitten. What was appealing to me is, I liked the fact that everyone knew everyone's name."
Another attraction, of course, is the Chester River, which has lured boaters and watermen for decades.
Houses along the water don't come cheap. When they become available, which isn't often, most sell for $250,000 to $850,000, local real estate agents say.
"It costs at least an extra $100,000 to look at the water," says Lisa Raffetto, an agent with Cooper Barroll.
Large restored Victorians and Colonials along some of the town's main streets sell in the $150,000 to $250,000 range. And buyers can find even better values -- houses as low as $75,000 -- if they are willing to buy a place that needs restoration.
Despite all its charming attributes, Chestertown is not utopia and has its share of problems, residents admit. On the north end of High Street, just blocks from the historic center of town, is a five-block square residents identify as a "crime zone," with drug dealing and prostitution.
Mrs. Bailey said local police and elected officials are aware of the problems and are trying to resolve them.
"We walked up there and asked the youngsters what they wanted," she says. "The boys wanted a basketball court. The girls wanted a stepping club."
The town is busy taking care of these requests, she says, hoping to give young people alternatives to hanging out or illegal activity.
