Top bar and grill in Chestertown, Maryland

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.

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.

The FREEZE is a popular food institution located at 717 Washington Avenue in Chestertown, Maryland. This cozy restaurant offers a variety of delicious frozen treats and comfort foods, making it a favorite spot for locals and visitors alike. With a welcoming atmosphere and friendly staff, The FREEZE is the perfect place to satisfy your cravings and enjoy a tasty meal with friends and family. Whether you're in the mood for a classic milkshake, a juicy burger, or a refreshing ice cream cone, The FREEZE has something for everyone to enjoy. Come stop by and experience the mouthwatering flavors and warm hospitality that make The FREEZE a must-visit destination in Chestertown.