Get your loved ones together for a weekend trip to Chestertown. This historic town sits along the Chester River, welcoming visitors to meader and browse its establishments and maritime heritage. For this itinerary, you will stroll down tree-lined streets and explore brick sidewalks lined with restaurants, inns, shops, and fine colonial residences.

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A weekend trip to Chestertown, Maryland can be a wonderful experience for your loved ones and a great change of environment for your canine friend. If you have ever visited Chestertown, let us know your favorite places to explore, and don’t forget to check out our previous article for more charming Maryland towns worth adding to your bucket list.

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