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Best Restaurants in Annapolis

Best Restaurants in Annapolis

Annapolis Maryland, USA Travel Guide

Culinary Overview

Cultural and Historical Context

The Chesapeake Bay shaped Annapolis's culinary identity for centuries. Watermen harvested its waters, bringing in an abundance of crabs, oysters, and fish. This tradition means seafood forms the backbone of local dining.

The use of certain spices and preparations reflects historical influences from European settlers and African American culinary traditions. The city's role as a meeting point for diverse populations also created variety in its food over time.

Ingredients and Flavors

  • Seafood: Blue crabs are paramount (steamed, in soups, crab cakes). Oysters (raw or fried), rockfish (striped bass), clams, and shrimp are local favorites.
  • Spices: Old Bay Seasoning is an iconic Maryland spice blend (celery salt, red pepper, black pepper, paprika). Locals sprinkle it on everything from steamed crabs and shrimp to French fries and popcorn.
  • Local Produce: Depending on the season, restaurants incorporate fresh fruits and vegetables from surrounding Maryland farms, a farm-to-table element to many dishes.
  • Sweet Corn: In late summer, Maryland sweet corn is a popular local delicacy.

Dining Customs and Etiquette

Dress Code

Dining ranges from very casual crab shacks (old clothes, messy) to upscale fine dining establishments (smart casual or dressier attire). Check the restaurant's website for specific dress codes.

Reservations & Tipping

For popular mid-range to fine dining restaurants, especially on weekends, during peak season, or for larger groups, making reservations in advance is common. Standard U.S. Tipping practices apply. Leave 15-20% of the pre-tax bill for good service. For exceptional service, 20% or more is common.

Meal Times & Structure

Breakfast (early morning-11:00 AM). Lunch (11:30 AM-2:00 PM). Dinner (kitchens open 5:00 PM, peak 7:00 PM-8:00 PM). Meals typically include appetizers, main courses, and desserts. Portions in U.S. Restaurants are generous. Sharing appetizers or main courses is acceptable.

Regional Variations within Maryland

  • Annapolis showcases classic Chesapeake Bay cuisine.
  • Baltimore has strong Italian and German culinary influences from its immigrant history, reflected in its deli culture and bakeries.
  • Western Maryland, closer to the Appalachian mountains, features different, more rustic fare.
  • For the quintessential Maryland seafood experience, Annapolis is a premier destination.

Must-Try Dishes

Signature Dishes

Steamed Blue Crabs

This is the quintessential Maryland experience. Blue crabs are steamed whole, typically seasoned generously with Old Bay Seasoning. They are served with mallets and knives for cracking shells. Many restaurants have "all-you-can-eat" crab feasts, with an immersive and messy experience.

A true Annapolis tradition!

Maryland Crab Cakes

Annapolis has some of the best crab cakes. These are made with a high proportion of fresh, sweet lump crab meat and minimal filler, then broiled or fried to a golden crisp. Look for "broiled" for a healthier option that highlights the crab flavor.

Minimal filler, maximum flavor.

Cream of Crab Soup & Maryland Crab Soup

Cream of Crab: A rich, creamy, indulgent soup with lump crab meat, often sherry and Old Bay. Maryland Crab: A distinct alternative, tomato-based with vegetables and crab meat, a lighter, brothier experience.

Two unique crab soup experiences.

Other Local Delicacies

  • Raw Oysters: From the Chesapeake Bay or local oyster farms, served on the half shell with cocktail sauce and mignonette. A fresh taste of the Bay.
  • Rockfish (Striped Bass): The Maryland state fish. Versatile and often prepared grilled, baked, or pan-fried, highlighting its flaky, white meat.
  • Soft Shell Crabs (Seasonal): In spring and early summer, blue crabs shed their shells. These are eaten whole, often fried or sautéed. A seasonal delicacy.
  • Smith Island Cake & Berger Cookies: Maryland's official state dessert, 8-10 thin layers of yellow cake with chocolate fudge frosting. Berger Cookies are a Baltimore classic, soft, cake-like cookies with a thick, fudge-like frosting.

Beverages & Street Food

Local Craft Beer & Orange Crushes

Maryland has a growing craft beer scene. Many Annapolis pubs and restaurants feature local breweries on tap. Orange Crushes are popular, refreshing cocktails with fresh-squeezed orange juice, vodka, triple sec, and a splash of soda water.

Maryland Wines & Street Food

Maryland produces some local wines. Annapolis does not have a large, established street food scene, but food trucks may appear at local events, festivals, or specific public locations.

Dining Options

Fine Dining

For upscale experiences.

  • Preserve: Farm-to-table cuisine with seasonal American dishes, local ingredients, refined atmosphere.
  • Treaty of Paris Restaurant (Maryland Inn): Classic American fare in a historic setting, an elegant dining experience.
  • Carrol's Creek Cafe: Upscale seafood and American cuisine with superb waterfront views across Spa Creek.

Mid-Range Restaurants

Popular choices for varied dining.

  • Boatyard Bar & Grill: Lively spot in Eastport, famous for seafood, especially crab cakes, nautical atmosphere.
  • Cantler's Riverside Inn: Classic, no-frills crab house experience, where locals go for steamed crabs.
  • Federal House Bar & Grille: Pub fare, local favorites, lively atmosphere on Market Space.

Budget & Markets

Affordable eats and local finds.

  • Pizzeria Paradiso: Casual, high-quality pizza.
  • Chick & Ruth's Delly: Famous Annapolis institution for breakfast, lunch, late-night, huge milkshakes.
  • Annapolis Farmers Market: Seasonal market on Riva Road, local produce, baked goods.

International Cuisine Options

Diversity in Dining

While seafood and American cuisine dominate, Annapolis also has a variety of international restaurants. You find Italian, Mexican, Thai, Indian, Japanese, and other global cuisines, especially on West Street and in areas further out from the historic downtown.

This has dining diversity for those seeking different flavors.

Beyond the Main Streets

Look beyond the immediate historic district to West Street and commercial areas for a broader selection of ethnic restaurants.

Online reviews and local directories indicate diverse choices.

Special Dietary Considerations

Vegetarian & Vegan

Many restaurants have marked options. Vegan selections are growing. Ask for modifications.

Allergen Awareness

U.S. Restaurants are good at accommodating allergies. Inform your server. Many menus indicate GF (gluten-free) options. Chefs typically answer questions on ingredients and cross-contamination.

Halal & Kosher

Limited dedicated Halal or Kosher restaurants. Some general restaurants may have dishes that happen to be friendly. Inquire directly in advance.

Resources

Use apps like Yelp, TripAdvisor, or HappyCow for filtering options. For severe allergies, a Chef card may be useful.

Culinary Experiences

Interactive & Learning Experiences

  • Annapolis Food Tours: Guided walking tours combine historical insights with food tastings at local eateries. This has a fun way to sample dishes and learn city history.
  • Cooking Classes: Occasional cooking classes may be at local culinary schools or specific restaurants. Check local event listings or the Annapolis Visitors Center for current opportunities.
  • Farm Visits: Surrounding Anne Arundel County farms sometimes have farm-to-table events, U-pick experiences (seasonal), or direct sales of produce.
  • Food Festivals: Annapolis hosts food-related events: Oyster Roast & Sock Burning (spring), various local seafood festivals (summer/fall). Check the Visit Annapolis website.

Unique Annapolis Dining Concepts

"Crab Feast" Experience

A full-blown crab feast is an Annapolis experience. It means sitting at a paper-covered table, armed with mallets and knives, picking steamed blue crabs. A casual, messy, quintessential Maryland tradition.

Don't be afraid to ask for a demonstration!

Waterfront Dining & Historic Taverns

Numerous restaurants have outdoor seating with views of the harbor, Spa Creek, or the Chesapeake Bay. This has a scenic backdrop for your meal. Dine or have a drink in historic taverns like Middleton Tavern, operating since the 1700s, for a glimpse into the city's past.

Local insights often point to hidden gems.

Food Tour Affiliate

GetYourGuide for Culinary Tours
Explore food tours and culinary experiences in Annapolis.
Book unique tastings and cooking classes.
Pre-book your spot for popular tours.
Read reviews from other food enthusiasts.
Search for "Annapolis Food Tour."
Miss Shirley's Cafe

A highly popular spot for creative breakfast and brunch dishes. Expect a wait, especially on weekends, but the unique menu items make it a rewarding choice.

  • Creative brunch menu.
  • Popular with locals and visitors.
  • Consider going early to avoid long waits.
O'Leary's Seafood Restaurant

A popular choice for seafood, known for its fresh fish and traditional preparations.

Fresh catch daily, ask about specials.

Additional Dining Resources

Local Blogs
  • Search for "Annapolis food blog" for local insights.
  • These often have hidden gems and new openings.
Visitor's Guide
  • The official Visit Annapolis website has restaurant listings.
  • Look for seasonal guides for best dining experiences.

Insider Tips for Dining

Maximize Your Crab Experience

Ask for a Demo

When enjoying steamed crabs, do not hesitate to ask for a demonstration on how to pick them. Locals are often happy to share their technique.

It makes the experience more authentic and enjoyable. | Practice makes perfect.
Seasonal Timing for Crabs

The peak blue crab season is typically late spring through fall (May to October). This is when they are most abundant and flavorful, for a great crab feast.

Best crab quality.
Oyster Season

Fall and winter months (traditionally months with an "R" in their name) are prime oyster season when the water is colder and the oysters are plump and firm.

Fresh and delicious.

Local Insights & Dining Flexibility

  • Ask Locals: Do not hesitate to ask locals for their favorite dining spots, especially for seafood. They often know the best hidden gems or the places with fresh, high-quality dishes.
  • Call Ahead: Call restaurants in advance to discuss specific dietary needs. This has the most accurate information and confirms accommodation.
  • Check Menus Online: Many restaurants post their menus online, helpful for reviewing options and prices before visiting.
  • Embrace the Mess: For crab feasts, dress casually and embrace the messy, hands-on experience. It is part of the fun!

Budgeting Your Meals

Lunch Specials

Many mid-range restaurants have lunch specials that are more affordable than dinner entrees. This has a way to try higher-end places on a budget.

Good value for a midday meal.

Markets and Deli Options

For budget-friendly meals, consider purchasing items from local markets or delis for picnics or preparing simple meals at vacation rentals with kitchen facilities.

Save money on dining out.

Additional Culinary Experiences

Dessert Focus

Do not skip Maryland's official state dessert, the Smith Island Cake, for an unique sweet treat.

Coffee Culture

Explore local coffee shops for a morning pick-me-up or a relaxed afternoon break. Many have unique atmospheres.

Happy Hour Deals

Many bars and restaurants have happy hour specials on drinks and appetizers, a way to sample different places at a lower cost.

Additional Tip for Dining

Always confirm operating hours before visiting, as they vary, especially outside peak season.

  • Check for seasonal closures.
  • Confirm holiday hours.
  • Book popular restaurants in advance.
  • Consider alternative dining times for fewer crowds.