TOP 20 Best Dining with family in Chestertown, Maryland

Chestertown Landing Apartments is a waterfront community situated at 100 Schooner Way in Chestertown, Maryland. Our luxurious apartments offer stunning views of the Chester River and are conveniently located near shopping, dining, and entertainment options. Residents can enjoy a variety of amenities including a swimming pool, fitness center, and community clubhouse. With spacious floor plans, modern finishes, and a prime location, Chestertown Landing Apartments provides the perfect blend of comfort and convenience for residents looking for upscale living in a picturesque setting.

Chestertown Cove Apartments is a luxurious residential community located at 408 Morgnec Road in Chestertown, Maryland. Our apartments offer modern amenities and spacious floor plans, perfect for those seeking a comfortable and convenient living experience. Residents can enjoy beautiful views of the cove and easy access to nearby shopping, dining, and entertainment options. With a friendly and professional management team on-site, Chestertown Cove Apartments is the ideal place to call home in the charming town of Chestertown.

Don Tonio's is a one-stop destination located at 6520 Church Hill Road in Chestertown, Maryland. This institution offers a variety of services including a food market, a liquor store, and a general store. Whether you're looking for fresh produce, a bottle of wine, or everyday essentials, Don Tonio's has you covered. With a convenient location and a wide selection of products, Don Tonio's is the perfect place to stock up on all your needs in one convenient stop.

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.

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.

BAD Alfred's Distilling is a unique institution located at 323 High Street in Chestertown, Maryland, United States. This brewpub and distillery offers house-made spirits, local craft beer, and delicious wood-fired pizzas. Established in 2018 by owners Al and Jennifer Cassinelli, Bad Alfred's continues to create small-batch craft spirits alongside an expanded cocktail, beer, and dining menu. Housed in a former historic garage and filling station, Bad Alfred's features an open and inviting dining room and bar that faces a glassed-in distillery space, allowing patrons to watch the spirit-making process while enjoying a drink, pizza, or live music. The back of the building has been transformed into a private event space with a bar, dining room, and conference space.

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.

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.

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.

Kent Plaza is a bustling shopping mall situated at 711 Washington Avenue in Chestertown, Maryland, United States. Conveniently located at the intersection of US Route 213 & Route 291, this institution is home to a variety of community-anchor tenants including ACME, Tractor Supply, and Walgreens. With a diverse range of stores and services, Kent Plaza is the perfect destination for all your shopping needs. Whether you're looking for groceries, home improvement supplies, or pharmaceuticals, you'll find it all at Kent Plaza. Visit us today and experience the convenience and variety that our shopping mall has to offer.

Village House is a one-stop destination for all your home furnishing and renovation needs. Located at 103 South Cross Street in Chestertown, Maryland, this institution offers a wide range of furniture, home goods, and contracting services. Whether you're looking to spruce up your living room with a new sofa, remodel your kitchen with custom cabinets, or simply find that perfect accent piece for your home, Village House has you covered. With a team of experienced professionals and a diverse selection of high-quality products, Village House is the go-to store for all your home improvement projects.

Kent County Visitors Info is a local government office and travel agency located at 122 North Cross Street in Chestertown, Maryland, United States. Our knowledgeable staff is dedicated to providing visitors with information about the many attractions, events, and activities in Kent County. Whether you're looking for recommendations on where to stay, dine, or explore, we are here to help make your visit to our charming county a memorable experience. Stop by our office or give us a call to start planning your trip today!

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.

Arby's is a popular fast food restaurant located at 707 Washington Avenue in Chestertown, Maryland. Known for its delicious roast beef sandwiches and curly fries, Arby's offers a convenient meal takeaway option for customers on the go. With a variety of menu options to choose from, including sandwiches, salads, and sides, Arby's is a great choice for a quick and satisfying meal. Whether you're looking for a hearty lunch or a tasty snack, Arby's has something for everyone. Visit us today and experience the mouthwatering flavors that have made us a favorite among food lovers in Chestertown.

McDonald's is a popular cafe, food, restaurant, and store located at 875 Washington Avenue, Chestertown, Maryland, United States. Our Terms and Conditions have recently changed, so please review them before continuing to use our services. With the Mobile Order & Pay app on iOS or Android, you can conveniently order and pick up your food at our store. We offer McDelivery through various apps like DoorDash, Uber Eats, Grubhub, and Postmates. You can also order through the McDonald's app for delivery. Menu items may vary by location, so check the app for availability.

The Driftwood Inn is a charming lodging establishment located at 609 Washington Avenue in the picturesque town of Chestertown, Maryland. This cozy inn offers comfortable accommodations and a warm, welcoming atmosphere for guests to relax and unwind. With its convenient location near the waterfront and local attractions, the Driftwood Inn is the perfect home base for exploring all that Chestertown has to offer. Whether you're visiting for business or pleasure, the Driftwood Inn provides a convenient and comfortable stay for all travelers.

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.