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

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

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

The Garfield Center for the Arts in Chestertown, Maryland is a multi function community center for the performing arts, and here you will find theater, music, films, children's programming and a whole lot more. With Educational Outreach programs run throughout the year offering seasonal workshops for the youth, and summer camps, the Garfield Center for the Arts engages the whole playmaker with mental, physical and artistic challenges. The theater, main stage and Kohl Lobby are available for rental for private events and special occasions. Come support the arts and check out the upcoming events.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

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

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

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

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

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