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Chestertown, Md.

Photos by Robert L. Drake

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A cruise up Maryland’s serene, unspoiled Chester River takes you to Chestertown, an amazingly well-preserved town of 2,000. Imposing pre-Revolutionary War buildings from the town’s days as a colonial Chesapeake Bay port of entry line the downtown waterfront. To the south lie Wilmer Park and the maritime campus of Washington College. (George Washington was a founding donor and sat on the board.)
Front and center downtown, at the foot of High Street, is the town dock, where the schooner Sultana is berthed. A cadre of shipwrights and 100 volunteers, plus townspeople and 2,500 schoolchildren, built and launched the 58-foot replica 10 years ago. Volunteers spent 200,000 hours abuilding, following the original 1767 plans, materials and techniques (and adding modern safety equipment).

Sultana ties Chestertown to its maritime heritage, then re-creates and spreads that heritage throughout Chesapeake Bay by taking children on educational voyages. So do the Echo Hill Outdoor School’s skipjack and buyboat, also docked on the waterfront.

You’re right downtown when you stay at Chestertown Marina (, or dinghy in from an anchorage, Chestertown Yacht and Country Club (1.5 miles south) or Rolph’s Wharf Marina, at buoy 35, about two miles south ( You also can tie up at the town dinghy dock next door.
Fishermen and farmers settled here decades before the first county courthouse was built in 1697. The 15-block National Historic District’s broad streets are lined with restored homes, brick sidewalks, pocket parks, flowering trees and gardens half-hidden behind brick walls and wrought-iron fences. You can stroll or bicycle (rentals available) randomly or follow the self-guided walking tour from Chestertown Marina. Noted are 24 structures ranging from the pre-Revolutionary War era to elaborate Victorian buildings of the 1880s railroad shipping boom.
As you’d expect in this unpretentious, quietly elegant town you’ll find art, clothing, fine crafts, rare books, wine tastings, gourmet coffees, artisanal breads and luscious pastries. Restaurants, also in historic buildings, range from pubs and pizza parlors to casual fine dining establishments. Often you can enjoy your meal or treat at an outdoor table. During the 1730 White Swan Tavern’s afternoon tea you can see some of the 70,000 artifacts unearthed during the 1978-’79 restoration. On Saturday mornings, Farmers’ and Artisans’ Market vendors set up in and around Fountain Park.
It’s ironic that tea is served here. In 1774 Chestertown patriots, incensed by British reprisals after the Boston Tea Party, attacked the (British) collector of customs’ brigantine in broad daylight and dumped its cargo of tea into the river. Thousands of locals and visitors, many in colonial costume, enthusiastically “attack” the Sultana each Memorial Day weekend. Then they celebrate their “victory” with parades, games, food, music and merriment.
Good times continue year-round at other festivals, First Fridays (downtown evening shop open houses) and performances at the Prince Theatre and other venues. However, it’s Chestertown’s commitment and connection to Sultana that sets it apart from other charming restored historic communities.
A “Downrigging Weekend” Oct. 27-30 will celebrate the 10th anniversary of Sultana’s launching and the end of the sailing season with fireworks, ship tours, sailings, children’s activities, parades, food and music. Dozens of tall ships and wooden yachts, from Delaware’s replica of the 1638 141-foot ship Kalmar Nyckel to the 1930s 11.5-foot Chesapeake Bay frostbiter 8-ball, will crowd the docks, their rigging illuminated in the evening.
This community’s embrace of its maritime history, afloat and ashore, is refreshing.,

See related articles:

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- Northeast Harbor, Maine

- Marblehead, Mass.

- Mystic, Conn.

- Oriental, N.C.

- Flamingo, Fla.

This article originally appeared in the August 2011 issue.