Chester River Outfitters in historic Chestertown, Maryland on the beautiful Eastern Shore, offer kayak rental, canoes and accessories as well as bicycle rentals, and are a full service bicycle and paddle shop. Rental boats and kayaks are also offered for sale and you will love paddling and canoeing the beautiful and numerous waterways in the area just waiting to be explored. Scenic country roads are just waiting to be explored by bike, and when renting a bike through Chester River Outfitters, locks and helmets are included. The also have a full-service bike shop for repairs as well as parts in the store. READ MORE

Banning House in Chestertown, Maryland is a beautifully restored family home perfect for self catering holidays just up from the Chester River. Enjoy a vacation rental that is within walking distance from everything, has a wonderful porch from which to watch the world go by, and an outdoor patio with grill. Banning House is located in the heart of the historic district of Chestertown, where guests can enjoy a stay in the spacious bedrooms with queen beds, a contemporary kitchen that is fully equipped, a sun room and dining room. A stay in this historic house originally built in 1785, offers perfect surrounds in a lovingly restored home.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

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

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

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

The Lauretum Bed and Breakfast Inn in Chestertown, Maryland reflects the late Victorian period, and is a unique setting for your visit to the Eastern Shore. The Lauretum Bed and Breakfast Inn has five guest rooms, two of them are two bedroom suites and include air con, free WIFI, hairdryers and ironing boards. When staying at the Inn, Country Club Privileges are available for all the facilities at the Chester River Yacht and Country Club, including the golf course and pool. This historic site bed and breakfast awaits you with wonderful features. 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

Brooks Tavern in Chestertown offers an eclectic mix of rustic and hip, and is housed in the historic site of the Radcliffe Mill, and they are open Tuesday through Saturday for lunch and dinner. Come eat, drink, relax and enjoy a wonderful dining experience in warm and hospitable surrounds, where good service and great food is the order of the day. The menu is seasonal and one to be proud of and here there is something delicious for everyone, and the wine list is in constant motion, come and enjoy a delight at Brooks Tavern, you'll be back.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