Private dining in Chestertown, Maryland

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.

The Kitchen at the Imperial is a charming restaurant located on 208 High Street in Chestertown, Maryland. This cozy eatery offers a diverse menu featuring delicious dishes made with fresh, locally sourced ingredients. Whether you're in the mood for a hearty breakfast, a satisfying lunch, or a decadent dinner, The Kitchen at the Imperial has something to satisfy every craving. The warm and inviting atmosphere, friendly staff, and top-notch service make this restaurant a must-visit for food lovers in the area. Come and experience the culinary delights of The Kitchen at the Imperial today!

The Waterfront at Washington College is a prestigious university located in Chestertown, Maryland, United States. Situated at 445 South Cross Street, this institution offers a picturesque and serene campus environment right on the waterfront. Students can enjoy stunning views of the water while pursuing their academic and extracurricular endeavors. With a strong emphasis on academic excellence and a vibrant campus community, The Waterfront at Washington College provides students with a comprehensive and enriching educational experience.

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.

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.

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.