Photography By Scott Suchman
Every Sunday, the same scene plays out at Scottie’s Shoe Store in downtown Chestertown. Owner Anna Cole arrives at 5 a.m. to take delivery of the newspapers - The New York Times, Washington Post, Philadelphia Inquirer. With some help, she hand-labels more than eight hundred of them, writing last names in the upper right corner with a bold black marker. By the time the doors open at six, rows of personalized papers fill more than half the floor space.
A parade of locals pours in, searching for their national news - and the latest goings-on in town. Cole greets everyone by name and hears plenty of “Hello, my dear” and “Good morning, Miss Anna.” “The shop is where people come to catch up on local news,” says Cole, who’s been selling shoes for thirty years and added the newsstand a decade ago.
In a way, she embodies Chestertown, a place right out of a Frank Capra movie. It’s a place where people still support mom-and-pop businesses, where personal service trumps Wal-Mart prices. A place where people not only know each other’s names but also care what’s happening in each other’s lives. It all boils down to community, that elusive thing that so many places aspire to but so few really seem to have.
When residents talk about Chestertown, they say things like, “It’s magnetic,” “It just grabbed me,” or “I was simply drawn here - I can’t explain it.” One woman even says, “I felt like someone sprinkled fairy dust on my head as soon as I arrived.”
Visitors sense it, too, as soon as they cross the Chester River. Here twenty-five miles northeast of the Chesapeake Bay Bridge, Kent County’s agrarian landscape gives way to a classic New England village, and everything seems different. People amble along brick sidewalks, stopping to chat with passers-by. Front doors are wide open on every side street, beckoning drop-in visits. American flags flap in the breeze above broad porches, and church bells mark every hour. It’s not history re-created to attract tourists but a thriving community that has retained its history - and a calmer way of life.
The town’s congenial character abounds at Play It Again Sam, the local coffee house and wine bar with outdoor seating. Clusters of people lounge on sofas and atop stools, surrounded by hometown artwork and a “Chestertown View of the World” mural with the town as the outsized center of the universe. A small crew churns out caffeinated concoctions, and a smattering of food selections, after capturing orders on Post-its rather than screeching them Starbucks-style. The atmosphere is as good as the coffee and encourages lingering. “People here have an appreciation for life,” says owner Peggy Mayberry, who moved to Chestertown five years ago after an extended search for a new place to put down roots. “They under-stand what’s important: family, home, community, neighbors. And there’s a respect for history that’s really important.”
Nearly 300 years of history are in plain view, where native and newcomers alike have painstakingly restored scores of historic buildings. Chestertown became the county seat of Kent - the Eastern Shore’s oldest county - in 1706, and erected its original courthouse in 1697. Today’s Italianate courthouse structure dates to 1860. As one of only six “Royal Ports of Entry” during Maryland’s colonial days, Chestertown attracted moneyed merchants who built grand Georgian homes near the water.
Today, the community of 4,746 boasts the state’s second-highest concentration of eighteenth-century homes (after Annapolis), as well as brick Federal-style homes, charming Queen Anne Victorians, and a few stunning Beaux Arts structures. “Pick up a walking tour map as soon as you get to town,” suggests Town Manager Bill Ingersoll, noting that it fills in most of the details regarding the town’s architecture and history.
Tobacco and wheat were mainstay crops for generations, but tea is what the locals still talk about and celebrate. In the spring of 1774, Chestertown residents learned that the British closed Boston’s port in retaliation for the Boston Tea Party. Angered by the news, they staged their own tea party, boarding the custom-collecting brigantine Geddes and hurling its tea into the Chester River to protest Britain’s exorbitant taxes. The annual Chestertown Tea Party Festival has been a Memorial Day tradition for almost thirty years.
To add more authenticity to the event, more than a hundred community volunteers completed a full-scale replica of the British Royal Navy ship Sultana to serve as the Geddes. Now the ninety-seven-foot schooner, built from 1998 to 2001, sails as the “schoolship of the Chesapeake,” a floating lab teaching thousands of students about Bay ecology and colonial history. The boat also hosts two-hour weekend cruises, departing seasonally from Chestertown and other Bay ports.
A short boardwalk lines Chestertown’s waterfront, also home to the old Wharf Inn steak and seafood restaurant, and many of the town’s stately homes. But the heart of town can be found in the bustling business district in the four blocks surrounding the town green. This Rockwellian space, known as Fountain Park, has a 105-year-old circular fountain at its center and a sextet of walkways leading to surrounding streets. “Everything emanates from there,” says Ingersoll, a Chestertown native.
On Saturday mornings, the whole town seems to start the day at a bustling farmers’ market, which runs April through December. Young couples with puppies and strollers mingle with retirees stocking up on fresh produce, flowers, and handmade crafts. “It’s the social hub of Saturdays,” says Caitlin Hawthorne, who moved back years after attending Chestertown’s Washington College, a highly regarded liberal arts school founded in 1782, with George Washington’s help.
“The college is one reason we’re such a cool town,” says Ingersoll. “Few places have so much going for it: a college town, colonial history, the county seat, a prosperous old downtown, and a vibrant shopping area.”
The shops, galleries, and restaurants surrounding the square keep residents and visitors busy for hours. On High Street, across from Fountain Park, Pride & Joy sells adorable children’s apparel, from taxicab yellow slickers to outfits sprinkled with ducks and crabs, while Houston’s Dockside Emporium stocks sportswear with a tropical flair. A few doors down is the decade-old Compleat Bookseller, run by Lanny Parks, who’s “always been in the book business,” as a librarian and teacher, before opening this family-friendly independent bookstore.
Around the corner, Twigs & Teacups brims with quirky household items, gifts, humorous books, and stationery. “Everyone comes here when they need a present for anyone,” says local resident and artist Nancy LaMotte. The Kerns Collection, a block down, displays LaMotte’s sea glass jewelry along with a rotating collection of wearable art, paintings, and home furnishings by an assortment of regional artists. The store sits in the original lobby of the Prince Theatre, opened in 1926 for vaudeville and later turned into a movie house. Much of the structure has recently been magnificently restored as a performing arts center, which attracts local and national theater companies, jazz musicians, singer-songwriters, and lecturers. The theater is just one outward sign of the community’s commitment to the arts. “As an artist, I was overwhelmed by how supportive the community was - it really impressed me,” says LaMotte, who encourages visitors to explore an expanding artisan enclave nearby on and around refurbished Cannon Street.
The Chester River Knitting Company launched the area in 1998, and now creates 700 to 800 sweaters annually on hand-operated machines, using all-natural fibers like cotton, wool, alpaca, and a rare six-ply cashmere. Nearby, Robert Ortiz Studios creates made-to-order Shaker- and Japanese-style contemporary furniture, while Vicco von Voss makes one-of-a-kind custom wood furnishings. Cannon Street’s newest addition is the Chestertown Old Book Company, where owner Gerard Cataldo stocks rare books and first editions. His wife, Rhonda Cataldo, opened the nearby Kettledrum Restaurant and Tea Room last year, serving innovative lunch and dinner fare as well as elegant afternoon tea.
Other restaurants include casual lunch spots like Feast of Reason with quiches, salads, and other light fare, and the Old Mill Bakery & Café, with soups, sandwiches, and wraps. The more upscale Blue Heron Cafe offers a soothing, light-filled setting for lunch or dinner and regional dishes like oyster fritters, soft crabs, crab cakes, and chicken penne pasta. The circa-1903 Imperial Hotel and Restaurant is a charming Victorian hotel with fine dining and a double veranda over the front entrance. Another downtown historic lodging option is The White Swan Tavern. Built as a private residence in 1733, it expanded into a tavern in the 1790s and has been impeccably restored as a bed and breakfast. One of The White Swan’s innkeepers, Wayne McGuire, summarizes the tavern and the town, when he says, “This place exudes history; it represents something.”
And people who live in Chestertown don’t want to lose touch with that sense of place, despite inevitable growth. “Whatever we do, we’re going to do it right,” says Mayor Margo G. Bailey, noting that a moratorium on building remains in effect into 2005 while the town updates planning and zoning documents. “We’re going to do it our way, not a developer’s way...and we will do what we need to do to make sure we don’t lose our identity.”
Karen-Lee Ryan is a Washington- D.C.-based freelance writer who loves to escape to the Eastern Shore between deadlines.
Locals’ Guide to Chestertown
Least Likely Name for a Coffee Shop: Play It Again Sam originally opened as a used record store with an old coffeepot. “No one bought records, but everyone came to drink the coffee,” says current owner Peggy Mayberry. The original owner changed it into a coffee shop about six months later, and she kept the name when she bought it nearly five years ago.
Best Late Night Spot: Andy’s is the only kitchen in town open until 11 p.m. weekdays and midnight Fridays and Saturdays. Plus, the casual bar and restaurant offers great live music on the weekends. 337 1/2 High St., 410-778-6779 or http://www.andys-ctown.com.
The Town Pets: Hobbes is a twenty-pound cat who doubles as CEO and night watchman for Twigs & Teacups gift shop and Lucy the Goose is a sometimes cranky and always vociferous oversized white bird who hangs out near the boardwalk along the Chester River.
Bring the Kayak: The Chester River is filled with osprey nests, wildlife and small coves, but few big boats, making it the ideal place to kayak.
Don’t Miss: The half-mile walk up Washington Street, past handfuls of ornate Victorian homes, to Washington College with dozens of brick colonial buildings and grassy knolls.
Contacts
Blue Heron Cafe
236 Cannon St., 410-778-0188
Chestertown Old Book Company
317 Cannon St., 410-810-3880
Chester River Knitting Company
306 Cannon St., 410-778-1480
http://www.sweatermakers.com
Compleat Bookseller
301 High St., 410-778-1480
http://www.compleatbookseller.com
Feast of Reason
203 High St., 410-778-3828
Houston’s Dockside Emporium
315 High St., 410-778-9079
http://www.chestertown.com/houstons/
The Imperial Hotel and Restaurant
208 High St., 410-778-5000
http://www.imperialchestertown.com
Kerns Collection
210 High St., 410-778-4044
http://www.chestertown.com/kernscollection/
Kettledrum Restaurant and Tea Room
117 Cross St., 410-810-1497
http://www.kettledrumtea.com
Old Mill Bakery & Café
207 S. Cross St., 410-810-8841
Play It Again Sam
108 S. Cross St., 410-778-2688
http://www.chestertown.com/playitagainsam
Pride & Joy
321 High St., 410-778-2233
http://www.chestertown.com/prideandjoy/
Prince Theatre
210 High St., 410-810-2060
http://www.princetheatre.org
Robert Ortiz Studios
207 S. Cross St., 410-810-1400
http://www.ortizstudios.com
Schooner Sultana
105 S. Cross St., 410-778-5954
http://www.schoonersultana.com
Twigs & Teacups
111 S. Cross St., 410-778-1708
http://www.chestertown.com/twigsandteacups
Vicco von Voss Furniture Design
312 Cannon St., 410-810-0267
The White Swan Tavern
231 High St., 410-778-2300
http://www.whiteswantavern.com
