On Sunday mornings, the Chestertown locals gathered at Scottie's Shoe Store never seem to be at a loss for words. In the company of proprietor Anna Cole, they discuss politics, the weather, corn and soybean prices. Everyone knows everyone at Scottie's, and few come for the shoes that are lined along one narrow wall of the store.
"There are not many towns I know of where the shoe store is the newsstand and gathering place, the gas station sells produce and the owner of the Christian bookstore takes in mending," Cole said laughing.
Cole has been in business on the Eastern Shore for 27 years at her High Street location across from the town square. In addition, she proudly says, while she grew up in nearby Worton, she has always worked in Chestertown and has been a resident "up on Elm Street" for the past 15 years.
"I love it here," she said, adding, "selling my papers and souvenirs ... just being in touch with all of the lifelong residents."
John M. Hamilton, an agent with O'Conor, Piper & Flynn ERA on High Street, says growth in the town proper, especially in terms of new housing, is not extensive, mainly because many younger people, born and raised in Chestertown, yearn for a more urban life where there are greater employment opportunities. Although the town attracts retirees, Hamilton says most residents commute to work, pointing out the 40-minute drive to Dover, Del., and the 90-minute drive to either Washington or Baltimore.
Chestertown, the Kent County seat, was founded in 1706 and served as a major mid-Atlantic port of entry during Colonial times.
Here is a town rich in history, immediately noticeable to visitors by the variety of its original architecture. Many of the public buildings boast fine examples of Italianate, Queen Anne and French-inspired Second Empire design, while the houses range in style from the Georgian mansions of Colonial merchants to ornate edifices of the Victorian era.
The average price for waterfront homes is around $350,000. Hamilton notes that housing in developments on the south side of the river costs between $325,000 and $350,000.
Ranchers, Colonials, and bungalows in nearby subdivisions such as Kingston Manor, Chesapeake Landing and the Grove average about $179,000. Quaint Victorian and Federal detached homes in town range from $76,900 to $169,000.
"Sometimes it takes awhile to get exactly what you want," Hamilton said. "Often you have to take what we have and make it what you want."
High Street, the broad, main thoroughfare, stretches from the banks of the Chester River to the chief public areas of town at Cross Street. Chestertown thrived during the 18th century, for the most part due to its being a trading center for the agricultural industry of the county.
Tobacco, then later wheat production, heralded prosperity in Revolutionary times.
The 19th and early 20th centuries were also good to the town and its economy, with fruit growing and a burgeoning railroad responsible for a doubling of the post-Revolutionary War population of 4,000 residents. Today's count has barely changed from that of the 1790 census.
Washington College, founded in 1782, was the first college chartered in the nation after the Declaration of Independence. With its current enrollment of about 1,400, it remains, as at the time of its founding, the 10th-oldest liberal arts institution in the nation.
For people choosing to settle in Chestertown, the town offers economic opportunities for small businesses.
There are 41 specialty shops, antique stores, crafts studios and galleries in the compact business district as well as a number of financial institutions, restaurants, taverns and cafes. Charming restored inns beckon to weekend visitors.
Having purchased a property in town 13 years ago, Pat McGuire and her husband leave their Bowie residence every weekend and head to their circa 1820 two-story home on High Street.
"You'll never write about a better town than this," she said. "I love the small college-town feel ... reminds me of Westminster, where I grew up."
McGuire, who manages a law firm in Greenbelt and whose husband is a judge, looks forward to the day when they retire to Chestertown.
"I'd like to live here forever," McGuire said.
ZIP code: 21620
Commuting time to downtown Baltimore: 90 minutes
Public schools: Garnett Elementary; Chestertown Middle, Kent County High
Shopping: Downtown Chestertown boutiques; Kent Plaza Shopping Center, Washington Square Shopping Center
Homes currently on market: 19
Average listing price: $280,031 *
Average sale price: $253,764 *
Average days on market: 367 *
Sale price as percentage of listing price: 90.62% ** Based on 22 sales in the past 12 months as compiled by Metropolitan Regional Information Systems Inc.