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 Imperial Hotel in Chestertown is the perfect gathering place for travelers and locals, with a delightful front room restaurant and bar serving eclectic contemporary cuisine. Here you can enjoy comfortable accommodations in the 11 deluxe rooms and 2 suites with balances of old world charm, quaintness and modern amenities. Private events are catered to here with meeting rooms, banquets and private dining available it's perfect for wedding receptions too. The Imperial Hotel offers wine tastings, and hotel packages, and an unforgettable stay is guaranteed.READ MORE

The Evergrain Bread Company in Chestertown, Maryland offers a passion for baking with delicacies produced by the owner and head baker. With delicious breads, pastries and savories available, enjoy something delightful at the coffee shop with excellent coffees on hand to match your delectable choice, and here you will find the perfect environment to relax and let the world pass you by. Come savour the divine, reconnect and have a moment to yourself in this beautiful space downtown. The Evergrain Bread Company is a gathering place for friends, locals and visitors, where good food and coffee await.READ MORE

Simply Bed and Bread is a wonderful guest house in Chestertown located close to the water and with two gracious rooms available you'll feel right at home. Enjoy a convenient stay close to the college campus, wonderful gifts shops and fine restaurants nearby and historic sites, and the area is perfect as a wedding destination with old world charm, as well as fishing, golfing, biking, birding and so much more. Simply Bed and Bread extends a warm welcome, and a wonderful stay is guaranteed. READ MORE

Kent County Arts Council offers arts for everyone, and helps fund, support, and produce the arts in the community. With many activities focused on local African American cultural heritage, as well as culture and heritage celebrations, the Kent County Arts Council supports community events, school cultural arts presentations, and individual artists. With the acquisition of the Charles Sumner Post #25, an incredible historic site and building which will become a world class museum, new and exciting developments are afoot in Chestertown, Maryland.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

Chestertown Riverarts Gallery is a non profit community arts center that offers gallery exhibits, weekend craft and art workshops, and there is a stunning gift shop with works if Eastern Shore artists and more. With a constantly evolving program of exhibitions, classes, lectures and special private events, Chestertown RiverArts inspires creativity, for community enrichment, and establishes the region as a premier arts destination. There's a clay studio, arts for kids and wonderful teachers offer a list of classes in many genres for all skill levels.READ MORE

The Chester River Association in Chestertown, Maryland is an advocate for the health of the Chester River and the living resources it supports. Come experience eco tourism and explore the waters firsthand, learn about riverkeeper programs, discover the creatures that share the river with you, participate in river events, and get out on the river. The Chester River Association strives to improve the quality of the water, educate the public and a whole lot more, help them achieve this, take action today.READ MORE

Chestertown Historic House offers fine antique furnishings and paintings in keeping with the history of this wonderful home. Enjoy watching the world go by from the porch in the heart of beautiful Chestertown, Maryland, and distant views of the Chester River. This circa 1780 and 1840 house provides a wonderful level of comfort in the master bedroom with his and hers bathrooms, two more bedrooms with private baths, a gourmet kitchen, controlled heating, air conditioning and so much more. Chestertown Historic House also has an outside grill, and is a simply wonderful place to stay as a self catering option when visiting Chestertown, Maryland.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