Chestertown's Charms 
By Nancy Breslau Lewis | July/August 2011
Driving across the Chester River Bridge into Kent County, Chestertown’s stately colonial-era mansions come into view along the opposite bank, indication that Chestertown is no ordinary Eastern shore town. The impression only deepens as visitors drive by tree-lined streets, brick sidewalks, green parks, and one-of-a-kind boutiques. Three hundred years of history are carefully preserved in the downtown historic district, along with all the modern amenities and cultural attractions that make this a must-see destination for Marylanders in search of a relaxing get-away.
Chestertown is a walkers’ paradise. To get oriented, stop by the mid 18th-century Custom House at 101 South Water Street, next to the public dock at the foot of High Street. A free 45-minute, audio-guided tour (created by Washington College) of the town’s waterfront area can be picked up there on Fridays from 12-4 p.m. and on Saturdays from 11 a.m.-4 p.m. The Geddes-Piper Museum at 101 Church Alley, a short walk away in the center of town, provides another view of Chestertown’s past. Each room of the museum (originally a merchant’s home built in 1784) presents furnishings and collections from a different era of the town’s history.
The heart of downtown lies at the intersection of High and Cross streets, where Fountain Park serves as a focal point for community activities. There, from the first Saturday morning in April through the last Saturday before Christmas, vendors and shoppers swarm an Artisans’ Market that features products made in Kent County. A Farmers’ Market fills the street adjacent to the park. First-time visitor Linda Berg observed: “The homegrown herbs and vegetables are incredible. I even found some locally produced lavender soaps!”
Lovely Lodging
If you decide to make a weekend out of it, check out the Imperial Hotel (410.778.5000) which sits in the 200 block of High Street overlooking nearby art galleries and shops. This historic 100-year-old hotel has 11 rooms and the elegant Front Room Restaurant. The White Swan Tavern (410.778.2300), a beautifully restored colonial building located across the street at 213 High offers six rooms. Also in the heart of the historic district is the beautifully restored John L. Stam House at 114 Washington Avenue. Visitors in search of a Victorian-era bed and breakfast can opt to stay in one of the five rooms at the Widow’s Walk Inn, located at 402 High Street (410.778.6455). For a more modern touch, the Holiday Inn Express (410.778.0778) and the Comfort Suites (410.810.0555) sit less than a mile north of the historic district, on Scheeler Road near Washington College.
Tucked away on the outskirts of Chestertown is the magnificent waterfront 18th century Great Oak Manor (877.502.6892). The bed and breakfast inn offers 11 guest rooms and a private beach.
Tempting Dining
For such a small town (population 5,000), Chestertown provides a surprising number of good restaurants. Start your day off with flannel cakes with apricot syrup at the Lemon Leaf Café by J.R. (117 South Cross Street). Later, dinner options abound from oyster fritters and crabcakes at the Blue Heron Café (236 Cannon) to savory quesadillas, burritos and tamales at Plaza Tapatia (715 Washington Avenue). Toast the sunset overlooking the Chester River at the Fish Whistle (98 Cannon Street).
For a snack or light morning or afternoon bite, stop by Against the Grain at 203 High Street. The European style bakery bakes flavorful breads and pastries daily.
Places of Interest
The historic district’s art galleries showcase handmade, contemporary furniture (Robert Ortiz Studios; 207 South Cross Street), unique carved items (Woodcarvings, Etc.; 308 Park Row), and paintings, textiles, and stained glass (The Artists’ Gallery at 239 High Street, Artworks at 306 Park Row, and Cannon Street Studios at 312 Cannon). There are also three bookstores within a couple of blocks of each other, and a number of sophisticated home goods and apparel shops.
Perhaps the most intriguing storefront is the Sultana Center (sultanaprojects.org), located at 105 South Cross Street. Back in 1997, plans were made in Chestertown to construct the Sultana, a near-exact reproduction of the kind of topsail schooner used to enforce tea taxes during the period leading up to the Revolutionary War. After tens of thousands of volunteer man-hours were spent building the ship, the Sultana was launched in 2001. Ever since, the schooner has crisscrossed the Bay, providing short public cruises, day-long educational experiences, and live-aboard programs that introduce both students and the general public to the history and environment of the Chesapeake. Two 2-hour public sails on the Sultana will leave Chestertown on both August 20 and August 27. Be sure to stop by the Sultana Center, or call 410.778.5954, to make a reservation.
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