The 30 Best Dine in in Chestertown, Maryland

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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.

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.

Modern Stone Age Kitchen is a unique institution located at 236 Cannon Street in Chestertown, Maryland. This innovative bakery, food store, and restaurant brings a modern twist to traditional stone age cooking techniques. Offering a variety of freshly baked goods, delicious meals, and a curated selection of specialty food items, Modern Stone Age Kitchen is a must-visit destination for food enthusiasts. Come experience a blend of old-world charm and contemporary flavors at this one-of-a-kind establishment.

Victory Farm is a charming institution located at 24420 Chestertown Road in Chestertown, Maryland. This unique establishment offers a combination of food and lodging, providing guests with a peaceful and serene retreat in the heart of the countryside. The farm is known for its fresh and delicious farm-to-table meals, made with locally sourced ingredients. Guests can also enjoy comfortable and cozy accommodations, perfect for a relaxing getaway. Whether you're looking to escape the hustle and bustle of city life or simply want to experience the beauty of rural Maryland, Victory Farm is the perfect destination for a memorable stay.

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!

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.

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.

Phat Daddy's BBQ, located at 205 Spring Avenue in Chestertown, Maryland, is a renowned catering company known for their mouthwatering smoked foods. With a secret rub and sauce, as well as top-notch smoking techniques, Phat Daddy's offers a unique and flavorful dining experience. In addition to their catering services, Phat Daddy's recently opened "The Shack" in Chestertown, specializing in on-site meat preparation, pick up, delivery, and catering for special events. Visit Phat Daddy's for a taste of award-winning BBQ that will leave you craving more.

KFC, also known as Kentucky Fried Chicken, is a popular fast food restaurant located at 709 Washington Avenue in Chestertown, Maryland, United States. Known for its delicious fried chicken and signature sides, KFC offers a variety of meal options for customers to enjoy. The restaurant frequently features special deals and promotions for customers to take advantage of, making it a favorite choice for a quick and tasty meal. Whether you're craving original recipe chicken or the famous KFC biscuits, you're sure to find something to satisfy your hunger at this location.

"The Prickly Pickle is a charming food establishment located at 827 High Street in Chestertown, Maryland. Known for its delicious and unique pickle-themed menu, this restaurant offers a variety of mouthwatering dishes that are sure to satisfy any pickle lover's cravings. Whether you're in the mood for a classic pickle sandwich or want to try a more creative pickle-infused dish, The Prickly Pickle has something for everyone. Come visit us and experience the delightful flavors of our pickled creations in a cozy and inviting atmosphere."

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.

Casa Carmen Wines is a charming bar and restaurant located at 312 Cannon Street in Chestertown, Maryland. This cozy establishment offers a wide selection of delicious wines from around the world, as well as a menu of delectable food options to pair with your drink of choice. Whether you're looking for a casual place to enjoy a glass of wine with friends or a romantic spot for a date night, Casa Carmen Wines has something for everyone. Come visit us and experience the warm and inviting atmosphere that makes us a favorite among locals and visitors alike.

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.

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.

Bee Crafty Collectibles is a charming furniture and home goods store located at 335 High Street in Chestertown, Maryland. Our store offers a unique selection of handcrafted furniture, home decor, and collectibles that will add character and style to any space. Whether you are looking for a statement piece for your living room or a special gift for a loved one, Bee Crafty Collectibles has something for everyone. Visit us today and discover the perfect piece to complete your home.

Welcome to the historic Chestertown bed and breakfast, the Inn at Mitchell House. Rated among the top ten out of 10,000 by "America's Historic Inns," this charming 18th-century manor home is situated on 12 manicured acres between Chestertown and Rock Hall, Maryland. Just a half mile away from the Chesapeake Bay, guests can enjoy the private beach and full services of the Tolchester Marina. Operating year-round, seven days a week, the inn offers six guestrooms, two parlors, a dining room, a screened porch, and numerous fireplaces creating a casual and friendly atmosphere. All rooms and the cottage include modern amenities such as a TV, hairdryer, iron, wireless internet, and use of the 2nd-floor refrigerator. Rates include a full country breakfast for two guests per room.

Located in Chestertown, Maryland, the Brampton Bed and Breakfast Inn offers comfortable and luxurious accommodations on 35 acres of landscaped gardens, meadows, and forest. With thirteen unique accommodations, including rooms in the manor house and private cottages, each room is carefully appointed with private en-suite bathrooms, luxury linens, smart TVs, and fast wireless internet. Enjoy a romantic retreat with amenities such as wood-burning fireplaces and modern ensuite bathrooms. The historic Brampton Inn, built in 1860 and listed on the National Registry of Historic Places, is a short distance from the quaint town of Chestertown and Washington College. Experience gourmet dining on the beautiful Renaissance Garden terrace or indulge in curated experiences such as a couples' float spa session or a private vineyard tour with wine tasting.

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.

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.

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.

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.