History buffs unite in this quaint southern spot.

The county seat of Kent County, Chestertown’s history predates the Revolutionary War. George Washington himself passed through many times en route to Philadelphia, and Washington College takes its name from him. 

Stop at the visitors’ center at Route 213 and Cross Street to pick up information on shops and attractions—and be sure to take the walking tour, which includes many historic buildings and restored residences. Visit

Garfield Center for the Arts at the Prince Theatre has a packed schedule of plays, lectures and events. Combine theater with dinner at the Imperial Hotel’s Front Room Restaurant next door. 

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Nearby Evergrain Bread Company is known for its artisan-crafted whole-grain breads and pastries. Soups, sandwiches and drinks are also available. 

Right in the center of town, Fountain Park is home to the Chestertown Farmers’ Market and Artisans’ Market every Saturday morning March-December. Concerts and special events also happen at the park in warm months.

Docked on the town’s waterfront at the end of High Street, the Sultana is a replica of a pre Revolutionary War British schooner. Daylong educational programs are available. 

Our Best of the Main Line Elimination Ballot is open through February 22!