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Weekends on the waterfront in historic Chestertown, MD

Do you find Annapolis just a bit too crowded, especially in the summer? For an enjoyable alternative, consider Chestertown. Situated on the banks of the Chester River and Chesapeake Bay estuaries, Chestertown offers outdoor recreation, art galleries, fine dining, and historic tours approximately an hour and a half from Baltimore.

The National Trust for Historic Preservation designated Chestertown one of its Dozen Distinctive Destinations for 2007, based on its “perfectly preserved 18th- and 19th-century homes,” gardens, and mix of restaurants, antique shops, and galleries downtown, all “along the drop-dead gorgeous Chesapeake Coast.” Best yet, a tour won’t cost you a penny—the Kent County Tourism Development Office has put together maps and self-guided walks so you can see the town’s main attractions at your own pace.

Additionally, if you can plan your visit during the first Friday of the month, you can enjoy extended shop and gallery hours throughout the downtown area as part of the monthly “First Fridays” celebration. Events typically run from 5 to 8 p.m.

Saturday mornings from April through December bring the weekly Farmers’ Market to Park Row, where you can sample local produce, homemade baked goods, plants, and more.

To start planning your Chestertown getaway, check out the resources on

Read more of the 50 Affordable Stateside Escapes.

Have a recommendation for Chestertown, or another great getaway within Maryland? Post your comment below!

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