What distinguishes Chestertown — over and above its picturesque setting, colorful history, exquisite architecture, and small-town charm—is its authenticity. This is no Disney-inspired re-creation. No siree! Mosey down any street in the former maritime, farming and milling center and come face to face with the past.
You can get acquainted with Chestertown in a few hours or, as time allows, delve more deeply over a day or more. The good news is that this is a walking town and you don’t need an itinerary. It is difficult, if not impossible, to get lost. However, if you like maps as I do and believe they enhance any visit, pick one up at the Visitor Center or in one of the downtown businesses.
Even without a map, if you keep your eyes open it’s hard to overlook the more than 60 scrupulously preserved historic sites (second in number only to Annapolis), the scenic riverfront, and local flora and fauna.
Duck into the maritime businesses, resurrected after hurricane Isabel tore a hole in the harbor, and walk along the Chester River while visualizing the town in its heyday as an important colonial port. For a view from the water (and I strongly recommend it), board the Sultana, a replica of a 1768 square topsail schooner, for a 2-hour cruise offered one or more times a month from April to November.
Unlike other destinations that assault visitors with neon, tee-shirts, fudge and trinkets made in Asia, Chestertown has a small number of choice shops and boutiques featuring antiques, furniture, and one-of-a-kind gifts, crafts, clothing and home furnishings. You’ll find them on and near High and Cross streets. Check out the Finishing Touch at 311 High St. for unusual picture frames, art supplies, stationery and local prints and crafts.
No Hollywood soundstage could do justice to the old-time Farmers Market every Saturday morning from April until the last Saturday before Christmas, at Park Row (between Cross Street and Spring Avenue) for produce, herbs, home-baked goods, and crafts.
History
In 1608 John Smith was allegedly among the first to set foot here. Chartered in 1706, Chestertown hosted its own tea party in 1774 when locals sympathetic to the Boston revolutionaries staged a symbolic gesture in the harbor. The annual Peggy Stewart Day reenactment in late May is reason enough to visit this hamlet, about an hour’s drive from Annapolis via the Bay Bridge, 50 East/301 North, and 213 North.
George Washington is said to have stopped frequently in Chestertown when traveling between Philadelphia and Virginia. Today, visitors from Philadelphia, Virginia and beyond come to enjoy the same fine hospitality in the town’s inns and restaurants.
The prosperous town burghers erected fine Georgian, Italianate and Victorian homes, and many have been lovingly restored. Some are open to the public, such as the Hynson-Ringgold house and the Geddes-Piper House (home of the Historical Society of Kent County).
Emmanuel Episcopal Church on Cross Street stands on the site where in 1790 the Episcopal Church split from the Anglican Church of England. You can be sure that made headlines. And although the local citizenry sided with the British in the War of 1812, they supported the Blue and the Gray during the Civil War. A High Street monument memorializes both sides.
A short drive from the town center is Washington College, founded in 1782. The 10th oldest college in the United States is still revered for its liberal arts curriculum and high academic standards.
Dining
Of course, one needs sustenance to digest so much history, culture and charm. When hunger strikes, head for any restaurant or cafe. (If you want fast food, get outta town.) In numerous visits over the past 20 years, I have never had a bad meal in Chestertown. A favorite, which I learned about from locals, is the Old Mill Bakery & Cafe, serving delicious, oversized sandwiches, salads, and homemade soups and chili. The pulled pork, smoked chicken, or curried chicken salad are outstanding. Somehow I always find room for a scrumptious cookie, to nibble at leisure. The cafe is open for breakfast and lunch Monday through Saturday.
For a more formal (and pricey) meal in genteel surroundings, head for the dining room of the distinctive and historic Imperial Hotel on High Street, open Sunday for brunch/lunch, Wednesday through Saturday for dinner. Seafood stars here. In warm weather, dine in the romantic garden out back where music is a fixture on summer weekends.
A worthwhile detour is the Kennedyville Inn on Route 213, a few miles north of Chestertown. The owners rib that “we’re in the middle of nowhere,” but the food is anything but nowhere. Serving seasonal Eastern Shore fare (the oyster fritters are sublime) and outstanding pit barbecue, the inn is open for dinner only, Wednesday through Sunday.
Holiday Events
In December Chestertown is lit up, well, like a Christmas tree. In fact, many Christmas trees are decked out in holiday finery and twinkling lights. If you’re a quart low on spirit, Chestertown is an idyllic and ideal refueling spot. Dickens himself couldn’t have done it better.
Holiday shopping—worlds away from noisy, crowded, stress-inducing megamalls—is a delight here. On Dec. 3, 10 and 17, many shops remain open until 8pm and serve refreshments.
By Beth Rubin
Leave A Comment