Best restaurants near me in Chestertown, MD

Price

$$
$$$
$$$$

Cuisine

AmericanItalianSteakhouseSeafoodFrenchIndian

Top Rated

CharmingDog-friendlyFancyGood for business mealsGood for groupsGood for special occasions

Dining Options

All dining options

Delivery only

Takeout only

Seating Options

BarCounterStandardHigh TopOutdoor

Accessibility

Wheelchair access

375 restaurants available nearby

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

1. The Retriever Bar & The Decoy Bottle Shop

4.8

Exceptional(88)

$$$$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 The Choptank - Annapolis restaurant

2. The Choptank - Annapolis

4.6

Exceptional(1638)

$$$$Price: Expensive

• Seafood • Annapolis

Booked 76 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 Osprey Point Restaurant restaurant

3. Osprey Point Restaurant

4.8

Exceptional(564)

$$$$Price: Expensive

• Contemporary American • Rock Hall

Booked 9 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 Rusty Scupper - Baltimore restaurant

4. Rusty Scupper - Baltimore

4.7

Exceptional(9026)

$$$$Price: Expensive

• Seafood • Inner Harbor

Booked 37 times today

Open, MON to THUR12:00 PM to 9:00 PMFRI and SAT 12:00 PM to 10:00 PM,SUN10:30 AM to 9:00 PM Happy Hour M-F3 PM to 6 PMOur Sunday Jazz Brunch 10:30 AM to 2:30 PM - $62 per person/tax/gratuity, for all brunch partiesIndulge 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 & King Crab Legs.Celebrate 2025 Father`s Day Buffet $82 at Baltimore's Best Brunch Destination! Enjoy a charming ambiance paired with a warm, inviting atmosphere & fantastic service. Make your reservation today. Come back & See usBook your table today : 410 727 3678

5. Rye Street Tavern

4.4

Awesome(595)

$$$$Price: Expensive

• American • Port Covington

Booked 53 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 Bridges Restaurant - MD restaurant

6. Bridges Restaurant - MD

4.6

Exceptional(2157)

$$$$Price: Moderate

• Contemporary American • Kent Narrows

Booked 19 times today

Bridges is an OpenTable "Top 100 Scenic View Restaurant in America". Located in the heart of the Chesapeake, Bridges restaurant offers unmatched waterfront dining featuring made-to-order dishes that are prepared from scratch using the finest hand-picked ingredients. Open daily for lunch and dinner, Bridges offers an award-winning happy hour Sunday through Friday. Come enjoy the spectacular views and taste the best of the Chesapeake Bay region!

A photo of Tagliata Restaurant restaurant

7. Tagliata Restaurant

4.7

Exceptional(2950)

$$$$Price: Expensive

• Italian • Harbor East

Booked 73 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*

8. The Ruxton

4.8

Exceptional(758)

$$$$Price: Very Expensive

• Steakhouse • Harbor East

Booked 36 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.Looking to elevate your dining experience, book your reservation in our beautiful wine cellar here: https://theruxtonsteakhouse.com/the-wine-cellar-experience/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

9. Chart House Prime - Annapolis

4.5

Awesome(7299)

$$$$Price: Expensive

• Seafood • Annapolis

Booked 70 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.

10. Bygone

4.7

Exceptional(3820)

$$$$Price: Very Expensive

• American • Harbor East

Booked 38 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.

Dining near Chestertown, MD at a glance

Updated on 7/16/2025

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From verified diners like you

A
AnthonyVIP
Baltimore / Maryland •47 reviews
4.0
Dined 2 days ago
Slow service was the only mar on an otherwise really good experience. This was my first time back since it re-opened and the place looks terrific and the food and drinks were very good.
More info
Rye Street TavernPrice: Expensive• American• Port Covington
•
4.4
K
KristyVIP
Chicago / Illinois •13 reviews
5.0
Dined 2 days ago
Good service and great food! Would definitely go back.
More info
Rusty Scupper - BaltimorePrice: Expensive• Seafood• Inner Harbor
•
4.7
N
Nikeya
Washington, D.C. Area •1 review
5.0
Dined 2 days ago
We like to bring our clients and employee staff here for business lunch/outing. The food is great and during the summer it's great to sit on the outside patio where is shaded and there's a nice breeze and scenery. The staff and customer service is very accommodating and nice. Choptank is one of our favorite go-to restaurants. The food is great and worth the price!
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The Choptank - AnnapolisPrice: Expensive• Seafood• Annapolis
•
4.6
L
Lee
Philadelphia County •7 reviews
5.0
Dined on Jul 6, 2025
Everything is consistently top notch and has been for years. Highly recommend.
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Osprey Point RestaurantPrice: Expensive• Contemporary American• Rock Hall
•
4.8
V
VickyVIP
Philadelphia County •12 reviews
5.0
Dined on Jul 5, 2025
This was our fourth dinner at The Retriever and we had another wonderful evening. The food is consistently very good, service is efficient and friendly and you can’t beat the cocktails. Plus it’s reasonably priced. We share incredibly fresh oysters and the smoked bluefish dip for starters. Among the four of us we had the shrimp burger, the pork and noodles and the catfish. Everyone enjoyed their entrees. We will definitely be back to this charming spot.
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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.

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Best restaurants near me in Chestertown, MD

Price

Cuisine

Top Rated

Dining Options

Seating Options

Accessibility

375 restaurants available nearby

1. The Retriever Bar & The Decoy Bottle Shop

2. The Choptank - Annapolis

3. Osprey Point Restaurant

4. Rusty Scupper - Baltimore

5. Rye Street Tavern

6. Bridges Restaurant - MD

7. Tagliata Restaurant

8. The Ruxton

9. Chart House Prime - Annapolis

10. Bygone

Dining near Chestertown, MD at a glance

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American

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