TOP 10 Best Family friendly restaurants in Chestertown, Maryland

Red Roof Inn & Suites Chestertown is a cozy and comfortable lodging option located at 160 Scheeler Road in Chestertown, Maryland, United States. This charming inn offers a variety of rooms and suites to accommodate guests, whether they are traveling for business or pleasure. The convenient location provides easy access to local attractions, restaurants, and shopping. Guests can enjoy amenities such as free Wi-Fi, complimentary breakfast, and a fitness center. With its friendly staff and affordable rates, Red Roof Inn & Suites Chestertown is the perfect choice for a relaxing stay in this picturesque town.

Procolino's Pizza, also known as Proc's, is a beloved pizza joint located at 711 Washington Avenue in Chestertown, Maryland. This cozy restaurant offers a wide variety of delicious pizzas made with fresh ingredients and flavorful toppings. Whether you're in the mood for a classic pepperoni pizza or something more adventurous like a BBQ chicken pizza, Procolino's has something for everyone. The friendly staff and casual atmosphere make Proc's the perfect spot for a quick bite to eat or a relaxed meal with friends and family. Come visit Procolino's Pizza and see why it's a favorite among locals and visitors alike.

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.

Tolchester Marina Inc is a charming waterfront establishment located at 21085 Tolchester Beach Road in Chestertown, Maryland. This institution offers a unique combination of a bar, food, and restaurant services, making it the perfect destination for locals and visitors alike. With picturesque views of the water, guests can enjoy delicious meals, refreshing drinks, and a relaxing atmosphere. Whether you're looking to grab a quick bite, enjoy a leisurely meal, or unwind with a drink by the water, Tolchester Marina Inc has something for everyone.

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.

Play It Again Sam is a cozy cafe and restaurant located at 108 South Cross Street in Chestertown, Maryland. This charming establishment offers a unique dining experience with a menu that features delicious food and beverages. Whether you're looking for a quick bite to eat or a relaxing meal with friends, Play It Again Sam has something for everyone. With its welcoming atmosphere and friendly staff, this cafe is the perfect spot to enjoy a cup of coffee, a tasty meal, or a sweet treat. Visit Play It Again Sam for a memorable dining experience in the heart of Chestertown.

China House is a popular Chinese restaurant located at 711 Washington Avenue in Chestertown, Maryland. Serving up delicious and authentic Chinese cuisine, this institution is a favorite among locals and visitors alike. From traditional dishes like General Tso's chicken and lo mein to more unique offerings, China House offers a diverse menu that caters to all tastes. The cozy atmosphere and friendly staff make dining here a truly enjoyable experience. So if you're in the mood for some tasty Chinese food, be sure to stop by China House on your next visit to Chestertown.

Occasions is a charming culinary gem located at 327 Cannon St in the historic town of Chestertown, Maryland. Specializing in delectable food offerings, this local business is dedicated to providing an unforgettable dining experience for every guest. Whether you're looking for a cozy spot to enjoy a leisurely brunch, a delightful lunch, or a sumptuous dinner, Occasions has something to satisfy every palate. Renowned for its warm and inviting atmosphere, Occasions is the perfect venue for celebrating life's special moments or simply enjoying a meal with family and friends. The menu features a diverse array of dishes crafted from the finest ingredients, ensuring fresh and flavorful meals that cater to various tastes and dietary preferences.

Courtyard Inn is a charming lodging establishment located at 6336 Church Hill Road in the picturesque town of Chestertown, Maryland. This cozy inn offers comfortable and well-appointed rooms, perfect for both leisure and business travelers. The Courtyard Inn provides a peaceful and relaxing atmosphere, making it an ideal place to unwind after a busy day exploring the nearby attractions or attending meetings in town. Guests can enjoy the convenience of being just a short drive away from local shops, restaurants, and historical sites. Whether you are visiting Chestertown for business or pleasure, Courtyard Inn offers a welcoming and hospitable environment for all guests.

Brookmeadow Apartments is a charming residential community located at 150 Flatland Road in Chestertown, Maryland, United States. Nestled in a peaceful and picturesque setting, Brookmeadow Apartments offers a variety of spacious and well-appointed apartment homes for individuals and families alike. Residents can enjoy modern amenities such as a swimming pool, fitness center, and beautifully landscaped grounds. With a convenient location near shopping, dining, and entertainment options, Brookmeadow Apartments provides a comfortable and convenient living experience for all.

510 Washington Ave. is a prestigious university located in the historic town of Chestertown, Maryland. Situated at 300 Washington Avenue, this institution offers a wide range of academic programs and opportunities for students to excel in their chosen fields of study. With a focus on academic excellence and a commitment to student success, 510 Washington Ave. provides a supportive and engaging learning environment for all its students. Whether you are looking to pursue a degree in the arts, sciences, or humanities, this university is dedicated to helping you achieve your academic and professional goals. Come join our vibrant community of scholars and learners at 510 Washington Ave.