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.

Chestertown offers a mix of modern and classic lodgings. Choose Great Oak Manor for a romantic, luxury bed and breakfast inn or Red Roof Inn & Suites for its discounted prices and pet-friendliness. Another great place to stay is Simply Bed and Bread, with a quaint and homey atmosphere.

Start your weekend off right by visiting the Historical Society of Kent County. It is the perfect place to learn about the heritage of Chestertown and the preservation of historic buildings. Browse the research library, publications, museum exhibits, and programs.

To fuel up, head to Luisa's Cucina Italiana. Penne Al Filetto Di Pomodoro with chicken or shrimp on a bed of freshly diced tomatoes makes for excellent lunch. You can also grab rustic sourdough miche or delicious croissants and coffee from the Evergrain Bread Company.

Marvel at the Chester River and surrounding scenery on a 65-foot, 1920s-style tour yacht. The Chester River Packet Company offers charter cruises on the river, giving passengers the chance to enjoy the natural beauty of historic Chestertown, its waterfront, and cuisines.

If you love books, you will spend hours at Book Plate. The bookstore features a curated selection of used and new books on every subject imaginable, with a focus on local authors and interests. Shop for classics, first editions, and rare books.

Another specialty shop to explore is the Bee Crafty Antiques & Collectibles. You will find painted furniture, custom-made signs, handcrafted local gems, and antiques.

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.