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

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

Village House in Chestertown, Maryland welcomes you to the home of needlepoint pillows, perfect for personal and corporate gifts, or a little something for yourself. An array of luscious pillows await with stunning designs and here you will find the finest in interior accents. The beautifully hand stitched pillows with the finest attention to detail are designed to compliment decor and will enhance any home whether your decor is contemporary, country casual, opulent, spare or urban chic, come browse the over 800 items on display.READ MORE

The Lemon Leaf Cafe in Chestertown, Maryland serves exquisite American cuisine with a twist and offers the best crab soup, freshest Maryland crab cakes and local oysters anywhere. Enjoy classic Eastern Shore cuisine in delightful surrounds, and they cater to private events and will take care of all the details for you. Ms Joanne's Bakeshop at the Lemon Leaf Cafe provides the heavenly desserts on offer, try the popular lemon meringue pie, or the coconut cream pie or signature brownie sundae and more, they're all divine, and can be specially ordered.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

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

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 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

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