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5. Chestertown, Maryland

Autumn visits to Maryland’s Eastern Shore, where soybean crops turn into fields of gold, should be a yearly trek. And with charming shops, mouthwatering restaurants and a "walk-able" downtown all nestled along the banks of the Chester River, Chestertown should be high on the go-to list.

What to see: Explore downtown and enjoy the historic architecture, specialty shopping, galleries and a waterfront promenade. Don’t forget to see what Washington College has going on while you visit. The college recently launched its "History on the Waterfront" one-hour walking tour on Fridays and Saturdays. The audio-guided tour allows participants to stroll along the historic waterfront and listen to music, re-enactments and firsthand accounts of life in the Colonial port.

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