TOP 30 Seafood dining in Chestertown, Maryland

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Luisa's Cucina Italiana is a charming Italian restaurant located at 849 Washington Avenue in Chestertown, Maryland, United States. With a warm and inviting atmosphere, this institution offers a taste of authentic Italian cuisine in the heart of Maryland. From traditional pasta dishes to savory seafood entrees, every meal at Luisa's is prepared with care and passion. Whether you're looking for a romantic dinner for two or a family gathering, Luisa's Cucina Italiana is the perfect spot to enjoy delicious food and create lasting memories.

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.

Channel Restaurant is a charming dining establishment located at 21085 Tolchester Beach Road in Chestertown, Maryland. Known for its delectable food and inviting atmosphere, this restaurant offers a wide range of dishes to satisfy any palate. Whether you're in the mood for seafood, steak, or a hearty sandwich, Channel Restaurant has something for everyone. With friendly service and a picturesque waterfront location, it's the perfect spot for a casual meal or special occasion. Come dine with us and experience the delicious flavors of Maryland at Channel Restaurant.

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.

Shore Crabbing is a charming seafood restaurant located in Chestertown, Maryland, United States. Specializing in freshly caught crabs from the nearby shores, this institution offers a unique dining experience for seafood lovers. Enjoy delicious crab dishes prepared with local ingredients and served in a cozy waterfront setting. Whether you're looking for a casual meal with friends or a special dinner with loved ones, Shore Crabbing is the perfect spot to satisfy your seafood cravings. Come and taste the flavors of the Chesapeake Bay at this must-visit restaurant.

Welcome to Jellyfish Joel's Beach Bar, located at 22170 Great Oak Landing Road in Chestertown, Maryland, United States. Our bar is not just a place to grab a drink, but a destination for boaters and beach lovers alike. At Jellyfish Joel's, we take pride in caring for your boat with passion and attention to detail. Our newly renovated on-premise accommodations offer comfortable rooms with amenities such as a mini fridge, private bathroom, and access to ice & coffee stations. Guests can enjoy free parking, free Wi-Fi, and access to the beach, outdoor pool, golf course, and more during their stay. The Lodge is open year-round and conveniently located for local events.