O'Connor's Pub and Restaurant in Chestertown, Maryland is an Irish style pub and restaurant that offers traditional and delicious Irish and local food, with generous portions and beautiful presentation. O'Connor's Pub and Restaurant offers a premium full bar too and visitors can enjoy a fine Irish whiskey, imported and domestic beers and arguably the best Guinness in town. The legendary Crab bisque soup, oysters and Maryland crab cakes, are award winning meals, and daily specials are also available. O'Connor's Pub and Restaurant caters to private events in the function room and courtyard, available for up to 150 patrons, come party.READ MORE

The Fish Whistle is a waterfront restaurant in Chestertown, Maryland overlooking the Chester River, and here it's all about the food, with excellent nightly specials. Enjoy exquisite American cuisine of burgers and wings, oysters and prime rib, delicacies from the sea, desserts and a late night bar menu. The Fish Whistle also offers a catering and take home menu of delights, and there are excellent specials and events happening all the time, come and enjoy a wonderful dining experience in great surrounds.READ MORE

Chestertown Natural Foods in Chestertown, Maryland offers natural and organic food and products, here you will even find vitamins and unique gifts. Striving to provide the best gourmet products available, Chestertown Natural Foods has knowledgeable personnel, is handicap and wheel chair accessible, caters to everyone and invites you to buy fresh and buy local. Services include nutrition consultation by appointment, speaking engagements, free educational literature, even free coffee and tea on a Saturday, a wide range of offerings and organic produce, and a whole lot more.READ MORE

Visit Sultana Projects in Chestertown for history, culture, natural environment, estuaryREAD MORE

The Finishing Touch shop in Chestertown, Maryland offers excellent personal and corporate gifts, and specialize in framing, fine art, select gifts, artist's materials, digital imaging and art reproduction. At the Finishing Touch you can find wonderful gift ideas and artworks with local prints and photography available as well as Chesapeake maps, duck stamp prints and even works by featured artists, plus they do custom framing. Come visit the Finishing Touch, where they strive to get it right the first time.READ MORE

Massoni Art in Chestertown, Maryland offers contemporary fine art, paintings, sculpture, photography and prints, and is the perfect place for that corporate gift. Enjoy wonderful exhibitions by gallery artists and visiting artists as well as a very strong on-line presence. Massoni Art brings art to the workplace and has worked in collaboration with architects, developers, interior design firms, art consultants, and non-profit organizations and more.READ MORE

Stepne Manor circa 1690 in Chestertown, MD offers a wonderful stay on a historic site and landmark in a manor house with wide covered porch. This stunning town manor house can comfortably sleep up to fifteen guests and has a large kitchen with dining table. Interior rooms are fully furnished and showcase unique architectural designs. Stepne Manor is within walking distance to downtown Chestertown, and is also the perfect venue for meetings and wedding ceremonies.READ MORE

The Brampton Bed and Breakfast Inn in Chestertown, Maryland is a romantic oasis perfect for private getaways and honeymoon accommodation and is a meticulously restored 1860 National Register manor house. This award winning bed and breakfast offers the grace and charm of a 19th century country estate, where you can leave the world outside the door, and simply relax in beautifully appointed guest rooms, that are comfortable with modern amenities, and there are secluded cottages available many with whirlpool tubs or spa showers, and all with unparalleled privacy. Freshly prepared a la carte breakfasts are served in the morning, and afternoon tea and refreshments await. The Brampton Bed and Breakfast Inn is also a dream Maryland wedding venue and perfect setting for your special day.READ MORE

The Bookplate in Chestertown, Maryland offers a wide array of books in a broad array of categories, and they emphasize the history of Chesapeake Bay with many books relating to the history, historical sites, colonial and revolutionary heritage of Maryland's Eastern Shore. The Bookplate is a wonderful place to visit and has an expanded section on maritime history, exploration, sailing, navigation, nautical fiction and tales of the sea, as well as the fields of art, architecture, design and so much more, here there is something for everyone's historical interest and taste.READ MORE

Widow's Walk Inn B&B is located in the historic district of Chestertown, Maryland, and is close to many historic sites, quaint gift shops, and fine restaurants. A stay at the Widow's Walk Inn B&B takes you back down memory lane to how things used to be, here you will find quiet tranquility, a soothing of the soul, and a lovely welcoming home with air conditioned rooms and ceiling fans. Enjoy antique furnishings and family treasures, relax on the rocking chairs or swing on the front porch, and simply enjoy.READ MORE