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From upscale to casual, this is the ultimate guide on the best Annapolis MD restaurants. Whether you want a quick bite or a place for a special occasion, restaurants in Annapolis have something for everyone. Let’s take a look at the best restaurants in Annapolis Maryland.

Best Restaurants in Annapolis: Elegant And Upscale

If you are looking to celebrate a special occasion, Annapolis has a selection of elegant and upscale dining establishments. These restaurants in Maryland’s state capital will give your taste buds a great meal alongside a sophisticated ambiance, and great service. Here are our top picks for an elegant dining experience in Annapolis.

Lewnes Steakhouse

Lewnes Steakhouse is a family owned restaurant that has all the vibes of old world elegance. If you are looking for something more contemporary and sleek, scroll down to our “trendy restaurants” in Annapolis section below. 

Lewnes Steakhouse is in the Eastport part of downtown Annapolis

This fantastic Eastport area restaurant is an old school, romantic place with great food and quality service. This is the place to go if you are looking for an intimate and quiet date night.

The cozy booths and dim lighting at Lewnes Steakhouse

Wedge Salad at Lewnes is a great starter option

While their steak is a must-try, this restaurant also has some amazing seafood as well as delicious sides. If they have the sea bass on special, be sure to order it. For sides, don’t miss the creamy mashed potatoes and the onion rings.

Sea bass special at Lewnes

Spinach side dish

Don’t forget to try their steak!

One of the best parts is that all the portions here are really big, so you will definitely have plenty of food and even some to take home.

Reynolds Tavern

A historic gem in downtown Annapolis, Reynolds Tavern offers a unique dining experience with its elegant Georgian architecture and refined menu. It’s the perfect spot for special occasions, offering afternoon tea and a sumptuous dinner in a beautifully restored 18th-century setting.

Chart House

Chart House offers a blend of fine dining and panoramic water views. This restaurant has massive windows that give the diners a unique waterfront dining experience. It is one of the best places to go to if you really want to wow your dining partner. 

Sun drenched dining room at Chart House

Specializing in fresh traditional seafood and succulent steaks, this upscale restaurant provides a memorable dining experience with impeccable service, overlooking Spa Creek and the Chesapeake Bay.

Harry Browne’s

Harry Browne’s is a great place for lunch and brunch. Their friendly staff and great food has been well known since they opened in 1979. It is located right near the state house. This Annapolis restaurant serves traditional Chesapeake fare, American fusion, as well as seasonal specialties on their seasonal menus. 

The restaurant features lunch, dinner, and brunch menus, along with a long wine list. The restaurant can also provide catering for offsite private events. The bar and lounge open daily at 4 pm.

Carrol’s Creek Cafe

Situated along the Severn River, Carrol’s Creek Cafe is known for its stunning water views and upscale American cuisine. The menu features fresh seafood, prime steaks, and an extensive wine list, making it a personal favorite for many. 

This popular Annapolis restaurant has also been mentioned on Food Network as one of the places to eat at in Annapolis. Enjoy their famous jumbo lump crab cakes while taking in the scenic beauty.

O’Learys Seafood Restaurant

For an elegant seafood experience, O’Learys Seafood Restaurant is a top choice. Known for its fresh fish and creative dishes, this restaurant offers a fine dining experience in a cozy, sophisticated setting, perfect for special occasions.

Latitude 38 Degrees

Latitude 38° is a great place for waterfront dining in Annapolis. It is located right next to the U.S. naval academy and has beautiful views. You can also host events here. The style is more historic and old world charm. If you are looking for a more trendy event venue check out Choptank below.

Best Restaurants In Annapolis: Trendy

If you are looking for a more fun and contemporary dining experience, Annapolis has many trendy restaurants that are popular. Here are some of the best Annapolis restaurants that also have a trendy vibe.

Parley Room

Parley Room is a sleek cocktail lounge and contemporary American restaurant. This Annapolis restaurant has a small dining room and fun bar area. They also have a large outdoor seating space when the weather cooperates. Located in downtown historic Annapolis this fun spot is inside a historic Annapolis house that has been converted into a hotel.

Parley Room is on the ground floor of Capital Hotel in Annapolis.

Delicious burrata and peaches at Parley Room in Historic Annapolis

The octopus at Parley Room

Enjoy a glass of wine or a craft cocktail along with one of their yummy food items. Popular menu items include the burrata as well as the octopus.

Iron Rooster

Known for its all-day breakfast and eclectic menu, Iron Rooster is a trendy spot with a lively atmosphere. The restaurant is famous for its homemade pop-tarts and inventive takes on classic comfort food, espeically their yummy fried chicken. 

Iron Rooster is also a really popular place for brunch in Annapolis. Enjoy their savory menu with some brunch cocktails. After indulging in their delicious food, you can take a short walk to the city dock to admire the water views and work off your brunch.

The Choptank

The Choptank is a huge two level restaurant that is right on the water in Downtown Annapolis. This restaurant is part of the Atlas Restaurant Group which has several other restaurants in Maryland and accross the country.

The Choptank has both indoor and outdoor seating with a large bar that has a sleek design. This place is very popular almost any time of day due to its prime location. Be sure to make a reservation ahead of time or be prepared to wait for a table.

The Choptank is right on the water

The restaurant boasts a huge outdoor seating area. This is the best place to watch boats go by in Annapolis. If you are inside at the bar, be sure to check out their happy hour. It is every weekday from 3 PM to 6 PM and has both food and drink specials. 

The beautiful venue and location also lend themselves well to hosting special events. You can contact the restaurant directly to know more about how to book one of their private rooms for a more exclusive experience. 

Level Small Plates Lounge

Level Small Plates Lounge offers a chic and modern dining experience with its innovative small plates menu. Perfect for sharing, the dishes feature locally sourced ingredients and creative flavor combinations. This small plates lounge is a great place to enjoy a craft cocktail and a glass of wine.

Sailor Oyster Bar

Sailor Oyster Bar is a trendy spot known for its fresh Chesapeake seafood and vibrant atmosphere. The brick walls and nautical decor create a cozy spot to enjoy oysters, smoked fish dip, and a colorful selection of tropical drinks.

Blackwall Hitch

Blackwall Hitch offers a blend of contemporary American cuisine and a stylish setting. With live music, outdoor seating, and an extensive menu featuring fresh seafood and craft beers, it’s a perfect spot for a trendy dining experience in historic Annapolis.

  • Address: 400 Sixth St, Annapolis, MD 21403
  • Website: theblackwallhitch.com

Best Restaurants In Annapolis: Casual Dining

If you’re looking for a relaxed and casual dining experience, Annapolis has plenty of options that offer delicious food in a comfortable setting. Here are four top casual dining spots in the city.

The Trophy Room At Graduate Hotel

The Trophy Room is a large restaurant and bar inside the Graduate Hotel in Historic Annapolis. This hotel is located in the middle of it all on West Street in Historic Annapolis. This hotel has a very unique design with its mix of vintage and modern furniture. The common areas have plush seating, and nautical accents like maritime maps, boat models, and naval flags. It is a popular choice for special events and weddigns. 

Trophy Room at the Graduate Hotel

The Trophy Room restaurant is the main restaurant at the hotel. It is very spacious with ample seating, making it perfect for large groups and families. If you are there with little ones there is plenty of space to park a stroller. 

Chick & Ruth’s Delly

A local favorite, Chick & Ruth’s Delly is known for its hearty breakfasts, oversized sandwiches, and friendly service. This iconic deli on Main Street has been serving Annapolis for decades and is a must-visit for a casual meal.

Boatyard Bar & Grill

Boatyard Bar & Grill is a casual waterfront restaurant that offers a variety of seafood dishes, burgers, and more in a nautical-themed setting. Known for its Maryland crab soup and dockside dining, it’s a great place to enjoy good food with views of the Fourth Street marina.

The outdoor space here is quite impressive. You can enjoy their blue crabs alongside craft beer and still be under the shade of a massive tent. When it comes to picking the best seafood restaurant, this is certainly a contender. Be sure to save room for dessert. The key lime pie here is fantastic.

Miss Shirley’s Cafe

Miss Shirley’s Cafe offers a casual and family-friendly dining experience with its award-winning breakfast, brunch, and lunch menu. Known for its Southern-inspired dishes, this cafe is a popular spot for comfort food lovers, especially during the warmer months.

Vin 909 Winecafe

Vin 909 Winecafe is a casual yet sophisticated eatery known for its wood-fired pizzas, seasonal small plates, and extensive wine list. The cozy, laid-back atmosphere makes it a perfect spot for a relaxed meal with friends or family.

  • Address: 909 Bay Ridge Ave, Annapolis, MD 21403
  • Website: vin909.com

Galway Bay Irish Pub

Galway Bay is a traditional Irish pub in the historic part of Downtown Annapolis. You can enjoy a cozy atmosphere with traditional Irish food and some Irish whiskey. This Annapolis restaurant also hosts special events like live music and pub quizzes. 

The restaurant has a variety of menus, including options for brunch, kids, and those who need gluten-friendly dishes. They are also famous for their house-made eggnog. 

  • Address: 63 Maryland Ave, Annapolis, MD
  • Website: 

Cantler’s Riverside Inn

Cantler’s Riverside Inn is highly rated casual restaurant that specializes in seafood. It is also located in Anne Arundel County but it is about 15 minutes from downtown Annapolis. 

This casual Annapolis restaurant a favorite spot with locals who love seafood. Be sure to try their classic crab cakes as well as their crab cake sandwich.

Middleton Tavern

Middleton Tavern is located right in the heart of Downtown Annapolis. The best part about this place is that it feels like you are stepping back in time! It first opened hundreds of years ago, in 1750. Famous Colonial Americans like George Washington, Thomas Jefferson, and Benjamin Franklin used to go there. 

It’s right in the middle of Annapolis. Parking can be tricky, so try to visit on a weekday. If you come early enough you can also snag their happy hour deals. 

Pusser’s Caribbean Grill

While many people have enjoyed dining at Pusser’s Caribbean Grill, this restaurant is due to close towards the end of 2024. If you want to try their tasty Caribbean fare or the famous Pusser’s painkiller, be sure to visit soon before they close.

The word is that Atlas Restaurant Group, who is also behind The Choptank, will be taking over the space to open new places. These new restaurants will include an Italian restaurant as well as a Mexican restaurant. 

Best Annapolis MD Restaurants: Summary

From elegant dining restaurants to casual places, there are tons of options when choosing between the best Annapolis restaurants. Annapolis Maryland restaurants have something for everyone from couples to families. For an intimate date night, check out Lewnes Steakhouse or Chart House. For a craft cocktail, check out The Parley Room. 

The wide variety of restaurant options make Annapolis the perfect place for a weekend getaway from Baltimore or Washington DC. You will definitely enjoy some great food and have an unforgettable experience in this historic city on Maryland’s Eastern Shore. You can find something for all your dining needs in this charming little capital city.

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