Chestertown: The County Seat of Kent County

Arts and entertainment fuel this Bohemian town in Maryland.

Making your way back to Md. 213, continue south to Chestertown. The county seat of Kent County, the town’s historic roots go back before the Revolutionary War. George Washington himself passed through the town many times going to and from Philadelphia, and Washington College takes its name from him. 

Stop at the visitor’s center at Md. 213 and Cross Street and pick up information on shops and attractions ( Make sure you take the walking tour (map provided at the visitor’s center), which includes many historic buildings and restored residences—some now repurposed into myriad shops, antiques stores (including a “gently used” bookstore on South Cross Street, The Bookplate), restaurants and artists’ galleries. An architectural guide is available online.

Several artists have working studios in town. Check out First Fridays in Chestertown, when shops, antiques stores and galleries are open late and special arts and entertainment are offered. 

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Garfield Center for the Arts at the Prince Theatre on High Street has a packed schedule of plays, lectures and special events. Combine theater with lunch or dinner at the Imperial Inn and Restaurant next door. 

Discover the taste of old world breads at Evergrain Bread Company on High Street, featuring organic, artisan-crafted whole-grain breads and pastries. Everything is baked the night before to ensure freshness. Soups, sandwiches and drinks are also available—it’s a place enjoyed by locals and visitors alike. 

At the center of town is Fountain Park, at High and Cross streets, with an ornate working fountain standing at its heart. Chestertown Farmers Market and the Artisans Market operate there every Saturday morning 8 a.m. to noon from March through December, with limited operation in the winter. Local growers and artisans offer fresh flowers, meats, cheese and vegetables, artwork and products like natural soaps, baskets and other crafts. Concerts and special events also take place at the park throughout the warm months.

Other events and activities throughout the year include an historic house tour, the annual Tea Party, a waterfront Tall Ship Festival and the county-wide Chestertown River Arts Studio Tour and Show.

Highlights not to miss: 

  • The schooner Sultana, based at the town’s waterfront at the end of High Street. Sultana is a replica of a pre-Revolutionary War British schooner. Day-long educational programs are available through the Sultana education program, including canoeing and kayaking. 
  • Chestertown RiverArts is a community arts center on High Street with ongoing exhibits and classes throughout the year for adults and children in painting, sculpture, fiber, mixed media, clay and more. 

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