Whether you’re visiting for a Navy event, a weekend getaway, or a special celebration, Annapolis has an incredible dining scene—from waterfront seafood to cozy cafés and upscale dining.

Here are some of our favorite go-to spots, organized by area to make planning easy.

Downtown Annapolis (DTA)

The heart of Annapolis—walkable, lively, and full of restaurants, shops, and waterfront views.

Upscale + Special Occasion

Osteria 177 – 177 Main St.
Italian/Mediterranean cuisine with a refined, upscale feel—perfect for a special night out.
Choptank – 110 Compromise St.
Elevated seafood with waterfront views and a vibrant atmosphere.
Red Red Wine Bar – 189 B Main St.
Intimate wine bar with thoughtfully curated food—great for a relaxed but elevated evening.

Seafood + Classic Annapolis

O’Brien’s Oyster Bar – 113 Main St.
Classic waterfront seafood in a prime downtown location.
McGarvey’s Saloon & Oyster Bar – 8 Market Space
Lively spot with a great raw bar and casual vibe.
Middleton Tavern – 2 Market Space
A historic Annapolis staple—known for oysters, seafood, and live entertainment.
Buddy’s Crabs & Ribs – 100 Main St.
A go-to for steamed crabs and hearty Maryland classics.

Casual Favorites

Iron Rooster – 12 Market Space
Comfort food and all-day breakfast—great for groups and families.
Federal House – 22 Market Space
Easy, casual dining in a central location—perfect between activities.
Chick & Ruth’s Delly– 165 Main St.
Iconic local spot known for crab cakes, milkshakes, and oversized portions.
The Big Cheese – 47 Randall St.
A hidden gem for quick, delicious sandwiches.
Potato Valley Café – 47 State Circle (Closed Sundays)
Fun, quick option with loaded baked potatoes and tons of topping choices.

Brunch + Daytime

Miss Shirley’s Café– 1 Park Place
A must-visit for brunch—creative dishes and a lively atmosphere.

Unique + Historic Experience

Reynolds Tavern & 1747 Pub – 7 Church Circle
A charming, historic space offering afternoon tea, cozy dinners, and a candlelit pub downstairs.

Eastport (Waterfront Dining + Local Vibe)

Just across the bridge from downtown, Eastport offers some of the best waterfront dining in the area.

Carrol’s Creek Café – 410 Severn Ave
Premier waterfront dining—excellent for brunch or a special dinner.
Chart House – 300 Second St.
Classic fine dining with incredible views of the water and Naval Academy.
Lewnes’ Steakhouse – 401 Fourth St.
A top-tier steakhouse—perfect for celebrations.
Boatyard Bar & Grill – 400 Fourth St.
Local favorite known for some of the best crab cakes in Annapolis.
Vin 909 Winecafé – 909 Bay Ridge Ave
Cozy neighborhood wine bar with great pizza and small plates.
Blackwall Hitch – 400 Sixth St.
Coastal-inspired menu with locally sourced ingredients and a stylish setting.

Just Outside Downtown

Worth the short drive for great food and unique experiences.

Severn Inn – 1993 Baltimore Annapolis Blvd
Beautiful views overlooking the Naval Academy—great for sunset dining.
Cantler’s Riverside Inn – 458 Forest Beach Rd
A true Maryland experience—casual, waterfront, and widely known for some of the best crabs around.
Amish Market – 2472 Solomons Island Rd
Not your typical restaurant—part market, bakery, deli, and fried chicken spot. Great for takeout and quick meals.
Mission BBQ – 2101 Somerville Rd
Reliable, casual barbecue with generous portions.

Vegan-Friendly Options

49 West Coffeehouse & Winebar
Try the Sarah’s Bowl with rice, broccoli, avocado, and tofu.
Metropolitan Kitchen & Lounge
Roasted eggplant lasagna made with vegan ricotta and mozzarella.
Mother’s Peninsula Grille
Veggie stir fry with fresh vegetables and teriyaki.
True Food Kitchen
Great plant-based options including a vegan pizza and plant-based burger.

local tips

Downtown Annapolis is very walkable—park once and explore
Hillman Garage is the easiest parking option downtown
Reservations are highly recommended on weekends and during USNA events
Traffic can be heavy during games and Commissioning Week—plan ahead

staying at the goat getaway

One of the best parts of staying at The Goat Getaway is having easy access to all of these restaurants—while also having the option to relax at home with a fully stocked kitchen, takeout, or a casual night in.