The 30 Best Restaurant with lively atmosphere in Chestertown, Maryland

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Uncle Charlie's Bistro is a cozy and inviting restaurant located at 834 High Street in Chestertown, Maryland. Our bistro offers a warm and welcoming atmosphere where guests can enjoy delicious and freshly prepared meals. From hearty breakfast options to satisfying lunch and dinner dishes, Uncle Charlie's Bistro is the perfect spot for a casual dining experience. Our menu features a variety of American classics with a modern twist, using locally sourced ingredients whenever possible. Whether you're looking for a quick bite to eat or a leisurely meal with friends and family, Uncle Charlie's Bistro has something for everyone. Come visit us and taste the flavors of Maryland at our charming bistro on High Street.

Howard's Tavern is a cozy and inviting bar located at 6520 Church Hill Road in Chestertown, Maryland. Known for its friendly atmosphere, delicious drinks, and tasty pub fare, this neighborhood spot is the perfect place to unwind after a long day. Whether you're looking to catch up with friends over a cold beer, watch the game on one of their big screen TVs, or simply relax with a cocktail, Howard's Tavern has something for everyone. Stop by and see why this local favorite has been a go-to destination for residents and visitors alike.

Watershed Alley is a charming restaurant located at 337 High Street in Chestertown, Maryland. This institution offers a unique dining experience with a focus on locally sourced ingredients and seasonal menus. Guests can enjoy delicious dishes in a cozy and inviting atmosphere, making it the perfect spot for a casual lunch or a special dinner. With a commitment to sustainability and supporting local farmers, Watershed Alley is a must-visit destination for food lovers in the United States.

The Shanty Beach Bar is a charming seaside establishment located at 21085 Tolchester Beach Road in Chestertown, Maryland. This cozy bar and restaurant offers a relaxed and laid-back atmosphere, perfect for enjoying a cold drink and delicious food while taking in stunning views of the beach. With a menu featuring fresh seafood, classic bar snacks, and refreshing cocktails, The Shanty Beach Bar is the ideal spot to unwind and soak up the sun. Whether you're looking for a casual meal with friends or a relaxing evening by the water, this beach bar is sure to provide a memorable experience.

Chester River Yacht & Country Club is a prestigious institution located at 7738 Quaker Neck Road in Chestertown, Maryland, United States. This exclusive club offers a luxurious and picturesque setting for members to enjoy a wide range of amenities and activities. From sailing on the beautiful Chester River to playing a round of golf on the pristine course, members can indulge in a variety of leisure pursuits. The club also features exquisite dining options, a state-of-the-art fitness center, and social events throughout the year. With its stunning waterfront location and top-notch facilities, Chester River Yacht & Country Club provides a sophisticated and welcoming atmosphere for those seeking a premier country club experience.