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

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

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 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

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 White Swan Tavern in Chestertown, Maryland is a historic site and landmark since the pre-revolutionary war days, and is nestled in the Chesapeake Bay Region. Enjoy new world tradition, peace and tranquility in this wonderful bed and breakfast that offers gracious afternoon teas and cater to private events like small conferences, weddings, and receptions. White Swan Tavern offers rooms and suites some with four poster beds, and old world charm, and there are two fully equipped apartments known as the Bittersweet Guest Suites available too. Start your day with a continental breakfast in your room or their tea room, and enjoy a free morning newspaper, WIFI, cable TV in the sitting room and so much more, come feel the history, and enjoy the privacy here, it's wonderful.READ MORE

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

Sophisticated Vintage in High Street, Chestertown, Maryland are purveyors of stylish finds, including vintage furnishings and accessories, contemporary decor, eclectic jewelry and so much more. Come view antique furnishings, artifacts and collectibles in wonderful surrounds, immerse yourself in a time gone by inside this peaceful oasis, and a really fun place to visit. Come shopping for gifts, a little something special for yourself, at Sophisticated Vintage everyone's taste is catered to, and pieces of timeless elegance and charming vintage await.READ MORE

At Empty Hangers in Chestertown, Maryland you will find brand name items, gently used clothing, shoes and purses, and they stock mostly women's clothing. Other items available here at this consignment boutique include baby and children's clothing, a nice selection of books, pictures and household items. Come accessorise your beach wear with stunning jewelry, belts and scarves and head out to the Eastern Shore and Chesapeake Bay. Empty Hangers also have baby blanket and photo frames as well as Longaberger baskets, well worth a visit.READ MORE

Chestertown Antique and Furniture Center in Chestertown, Maryland offers antique furnishings, on-line auctions, and even Amish outdoor furniture and Amish play sets. Here you will find stunning items including recliners, original pieces, sofas and chairs, even unfinished furniture, desks, bookcases, entertainment centers and so much more. Chestertown Antique and Furniture Center also have bedding, china cabinets, as well as china, glass and silver, a visit is must, and it's a sure bet you won't leave empty handed.READ MORE