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Best restaurants near me in Chestertown, MD

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AmericanItalianSteakhouseSeafoodFrenchIndian

Top Rated

CharmingDog-friendlyFancyGood for business mealsGood for groupsGood for special occasions

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All dining options

Delivery only

Takeout only

Seating Options

BarCounterStandardHigh TopOutdoor

Accessibility

Gender-neutral restroomWheelchair access

375 restaurants available nearby

A photo of The Retriever Bar & The Decoy Bottle Shop restaurant

1. The Retriever Bar & The Decoy Bottle Shop

4.8

Exceptional(53)

$$$$Price: Moderate

• American • Chestertown

Booked 6 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 Tagliata Restaurant restaurant

2. Tagliata Restaurant

4.8

Exceptional(2798)

$$$$Price: Expensive

• Italian • Harbor East

Booked 86 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 The Ruxton restaurant

3. The Ruxton

4.8

Exceptional(501)

$$$$Price: Very Expensive

• Steakhouse • Harbor East

Booked 75 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 Chart House Prime - Annapolis restaurant

4. Chart House Prime - Annapolis

4.6

Exceptional(7110)

$$$$Price: Expensive

• Seafood • Annapolis

Booked 66 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 Cooper's Hawk Winery & Restaurant - Annapolis, MD restaurant

5. Cooper's Hawk Winery & Restaurant - Annapolis, MD

4.4

Awesome(7147)

$$$$Price: Moderate

• American • Annapolis

Booked 88 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 Rye Street Tavern restaurant

6. Rye Street Tavern

4.5

Awesome(358)

$$$$Price: Expensive

• American • Port Covington

Booked 45 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

7. Osprey Point Restaurant

4.9

Exceptional(547)

$$$$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 The Choptank - Annapolis restaurant

8. The Choptank - Annapolis

4.6

Exceptional(1471)

$$$$Price: Expensive

• Seafood • Annapolis

Booked 52 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 Acqua al 2 - Annapolis restaurant

9. Acqua al 2 - Annapolis

4.7

Exceptional(840)

$$$$Price: Expensive

• Italian • Annapolis

Booked 57 times today

Located in the heart of Annapolis, Acqua al 2 offers an authentic Tuscan dining experience. Featuring a wide array of vegetarian pasta, hand-carved steaks, and fresh seafood, as well as an extensive Italian wine list, Acqua is perfect for a celebratory dinner, an intimate date night, or a low key get-together with friends.

A photo of Bygone restaurant

10. Bygone

4.6

Exceptional(3641)

$$$$Price: Very Expensive

• American • Harbor East

Booked 45 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.

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Dining near Chestertown, MD at a glance

Updated on 1/15/2025

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MARTA

4.8

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From verified diners like you

From verified diners like you

D
David
Baltimore / Maryland •50 reviews
5.0
Dined 1 day ago
Great service and great food. Expensive, but a great experience.
More info
Tagliata RestaurantPrice: Expensive• Italian• Harbor East
•
4.8
N
Nancy
Philadelphia County •2 reviews
5.0
Dined 1 day ago
Very pleasant experience it was my sisters birthday they gave her a card and a free dessert with a candle the staff were very nice and the food was great quality
More info
The RuxtonPrice: Very Expensive• Steakhouse• Harbor East
•
4.8
D
Donna
Baltimore / Maryland •2 reviews
5.0
Dined 2 days ago
I visited for a work related lunch. The restaurant was not crowded, so we had a spot to ourselves. The food was delicious. The service was perfect (attentive, not smothering). Lots of free parking across the street and connected by an elevated walkway. I would do a business lunch here again.
More info
Cooper's Hawk Winery & Restaurant - Annapolis, MDPrice: Moderate• American• Annapolis
•
4.4
J
Jeremy
Baltimore / Maryland •6 reviews
5.0
Dined 4 days ago
Food and service was great. Someone in our party had a food allergy and they went above and beyond to make sure the food was prepared correctly and I was impressed when they even said they modified my meal because they were worried about cross contamination.
More info
Chart House Prime - AnnapolisPrice: Expensive• Seafood• Annapolis
•
4.6
J
JillVIP
Baltimore / Maryland •8 reviews
5.0
Dined 6 days ago
Excellent as usual. It was a perfect night for the butternut squash soup and a few OP oysters. We even tried the break-even scotch tonight too. 🥃
More info
The Retriever Bar & The Decoy Bottle ShopPrice: Moderate• American• Chestertown
•
4.8

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Here are the most popular cuisines: American, Seafood, Contemporary American, Italian, Steakhouse and many more.

There are 432 restaurants on OpenTable in Baltimore / Maryland.

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