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Restaurants near Chestertown Railroad Station

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377 restaurants available nearby

A photo of The Retriever Bar & The Decoy Bottle Shop restaurant
4.8
Exceptional(51)
Price: Moderate
• American • Chestertown
Booked 10 times today
The Retriever is a bar with great dining and the most extensive spirits selection around. Please note that even though we serve food we are classified as a bar and all guests must be 21 years old.
A photo of Cooper's Hawk Winery & Restaurant - Annapolis, MD restaurant
4.4
Awesome(7115)
Price: Moderate
• American • Annapolis
Booked 138 times today
Experience the perfect fusion of award-winning wines, Napa-style tasting rooms, and modern casual dining at Cooper's Hawk Winery & Restaurants. Enjoy contemporary American cuisine influenced by international flavors from our scratch kitchen. Each dish is expertly paired with our selection of wines for the best food and wine match. Whether you explore the tasting room for a pre- or post-dinner adventure or join the world's largest wine club, we believe in the power of food and wine to create lasting connections. Dining reservations are highly recommended, but walk-in guests are always welcome on a first-come, first-serve basis. Gluten-free and vegetarian dishes are available.
A photo of Tagliata Restaurant restaurant
4.8
Exceptional(2787)
Price: Expensive
• Italian • Harbor East
Booked 66 times today
Tagliata, an Italian chophouse, boasts an impressive menu featuring hand cut steaks, fresh rolled pastas, house made charcuterie & bounty of fresh seafood. Tagliata offers the largest wine list in Baltimore with bottles from around the world & a focus on Italian wines. We host live music in the piano lounge. Open windows overlook our majestic courtyard, which is illuminated with strung lights & features an seasonal outdoor bar.The suggested dress is business casual. We kindly ask our guests to abide by these suggestions to create an enjoyable environment for all guests.The following items are prohibited however:• Gentlemen’s tank tops or sleeveless shirts• Hats are not permitted indoors for gentlemen• No exposed undergarments• Clothing with language or graphics that are vulgar or sexually explicit• Footwear is required, however there is no restriction on the style*Children accompanied by an adult are not subject to the Dress Policy*
A photo of Chart House Prime - Annapolis restaurant
4.6
Exceptional(7082)
Price: Expensive
• Seafood • Annapolis
Booked 69 times today
Original Hospitality. Creative Culinary. Modern Energy.Experience the evolution of dining with Chart House Prime - where sophistication meets trendsetting cuisine. Our approachable yet professional service, coupled with the finest ingredients, brings you the best in refined seafood and steakhouse cuisine with a unique fusion of elegance and vibrance, creating a truly remarkable experience.
A photo of The Choptank - Annapolis restaurant
4.6
Exceptional(1457)
Price: Expensive
• Seafood • Annapolis
Booked 93 times today
Local Chesapeake Seafood and Crabhouse featuring live entertainment, craft cocktails, carefully curated wine list, and the best scenic view of the Chesapeake in the region!
A photo of The Ruxton restaurant
4.8
Exceptional(467)
Price: Very Expensive
• Steakhouse • Harbor East
Booked 76 times today
Curated by Aaron Taylor, Atlas Restaurant Group’s Corporate Chef & Chef Partner in this concept, the menu puts steak in the spotlight with over 11 cuts from Chicago-based meat purveyor Meats by Linz. The Ruxton will serve a mix of wet and dry aged prime cuts of Black Angus Beef, as well as dry aging Long Island Duck and Bison from Virginia’s New Frontier Farm in-house. To complement the steak options, seasonal shellfish and seafood entrees will be available including dover sole, Maryland rockfish, whole live lobster, king salmon, Chilean sea bass and more.The Ruxton will serve lunch every weekday and dinner 7 days a week. Be sure to visit Atlas’ new world-class cocktail bar and lounge next door to The Ruxton called Order of the Ace.
A photo of Rye Street Tavern restaurant
4.5
Awesome(333)
Price: Expensive
• American • Port Covington
Booked 83 times today
Rye Street Tavern's menu is thoughtfully created featuring seasonal changes, locally sourced ingredients, & a diverse selection that caters to every palate, including vegetarian and gluten-free options. From fresh seafood & house-made pastas to southern-inspired dishes, each meal is crafted to perfection. Rye Street Tavern promises an exceptional lunch, dinner, or weekend brunch dining experience for locals & visitors alike. Guests can enjoy a variety of dining environments, including an open kitchen with U-shaped leather booths, a stylish bar and oyster bar with panoramic Patapsco River waterfront views, & a spectacular outdoor dining area with a 75-seat island bar. Happy Hour offered Monday through Friday with half off of oysters on the half shell plus discounted beers, wines, & select cocktails.
A photo of Osprey Point Restaurant restaurant
4.9
Exceptional(544)
Price: Expensive
• Contemporary American • Rock Hall
Booked 2 times today
Our fine dining restaurant has a reputation for being one of the best in Kent County. We pride ourselves on having a fresh seasonal menu, high quality ingredients and a chef that puts care into preparing every meal. The dining room's casual elegance will make you feel at home whether you are stepping off the dock or celebrating that special occasion. Please stop in for a drink and hors d'oeuvres at the bar or make a reservation for dinner. We welcome transient boaters throughout the season and offer free dockage while dining in our restaurant.
A photo of Bygone restaurant
4.6
Exceptional(3619)
Price: Very Expensive
• American • Harbor East
Booked 34 times today
A fusion of the old, the new and the best of Baltimore. We’re an American gastro bistro that represents historic, vibrant, authentic Baltimore. We blend modern energy with a classic feel, celebrating luxury, excitement & an elevated dining experience. Plus, we’ve got some unbeatable views of our beautiful city!Bygone’s warm & welcoming atmosphere is reminiscent of an old-school social club, while our open rotisserie grill, whiskey bar & craft cocktails add a flair that is contemporary.Please note: No shows and cancellations made within less than 24 hours will be subject to a $75/per person fee.
A photo of Rusty Scupper - Baltimore restaurant
4.7
Exceptional(8868)
Price: Expensive
• Seafood • Inner Harbor
Booked 43 times today
Open, MON to THUR3:00 PM to 9:00 PMFRI and SAT 12:00 PM to 10:00 PM,SUN10:30 AM to 9:00 PM Our Jazz Sunday Brunch 10:30 AM to 2:30 PM. $62 per person/tax/gratuity, parties 6 or moreIndulge in an unforgettable dining experience with that special someone, as you take in breathtaking views of the city. When in Baltimore join us & enjoy the freshest seafood along with sweeping Inner Harbor views & hands down the most hospitable service in town.We offer a tempting array of local seafood specialties from Maryland Jumbo Lump Crab Cakes, Lobster Tails, Crab Stuffed Shrimp, Pan-Seared Chilean Sea-bass, Grilled Mahi-Mahi, Swordfish and King Crab Legs.Happy Hour: 3 - 6 Monday to Friday. Celebrate the season with us this Christmas and New Year’s Eve Fireworks Extravaganza Party 2025. Enjoy a festive ambiance, all your holiday favorites, and a warm, welcoming atmosphere. View our menus online & Call us for tickets.Come back & see us!Reserve your table today : 410 727 3678

See what locals rave about

From verified diners like you
From verified diners like you
  • Patricia
    Baltimore / Maryland •4 reviews
    5.0
    Dined 1 day ago
    I really enjoyed date night here! Whoever they have playing the piano and singing on Friday nights is amazing. It really set the tone, and the service is top notch. I will definitely be back!
    More info
    Tagliata RestaurantPrice: Expensive• Italian• Harbor East
    4.8
  • Gillian
    New York City •7 reviews
    5.0
    Dined 3 days ago
    The Retriever has a cozy, comfortable atmosphere. The food is excellent. I had shucked oysters (on Special) and a fried chicken sandwich served with fries; my husband had clam chowder and a house burger with fries. The dining room is at the back of the building, set apart from the long bar, which was quite busy on a Thursday evening. There was a "buzz" in the air, but the room was not noisy at all. Highly recommended!
    More info
    The Retriever Bar & The Decoy Bottle ShopPrice: Moderate• American• Chestertown
    4.8
  • Susan
    Baltimore / Maryland •1 review
    5.0
    Dined 4 days ago
    Our family's Christmas dinner experience at Chart House in Annapolis was incredible. The dinner was delicious and the service was impeccable. Our waiter made perfect recommendations regarding wine choices and dinner entrees and was attentive throughout our dining experience.
    More info
    Chart House Prime - AnnapolisPrice: Expensive• Seafood• Annapolis
    4.6
  • Michael
    Washington, D.C. Area •2 reviews
    5.0
    Dined 4 days ago
    The staff was wonderful on Christmas Eve! Our server Julia was awesome and super accommodating. Elsa, the manager was very sweet and sent my wife an amazing dessert for her Birthday. We had a great time and the views from the upper level at Christmas were beautiful. There were some rowdy Christmas revealers at the bar but Elsa quieted them down. 😎 I highly recommend the restaurant for any occasion. We had a party of seven and everyone left very happy and satisfied.
    More info
    The Choptank - AnnapolisPrice: Expensive• Seafood• Annapolis
    4.6
  • Norman
    Baltimore / Maryland •2 reviews
    5.0
    Dined 5 days ago
    Wonderful experience, enjoyed Birthday dinner with my son, knowledgeable staff, excellent service, stunning food and presentation. I look forward to returning to try other items.
    More info
    Cooper's Hawk Winery & Restaurant - Annapolis, MDPrice: Moderate• American• Annapolis
    4.4
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