Annapolis, Maryland, isn’t just about historic charm and waterfront views—it’s a foodie’s dream with an unbeatable dining scene.
From cozy cafés to upscale seafood spots, this city packs a punch when it comes to flavor.
Whether you’re craving Chesapeake Bay crabs, farm-to-table goodness, or global cuisine, Annapolis has something for every palate.
Ready to dig in? We’ve scoured the city to bring you the absolute best restaurants in Annapolis MD—places that’ll make your taste buds sing.
These spots aren’t just meals; they’re experiences worth savoring. So loosen your belt and get ready—this list is your golden ticket to Annapolis’ tastiest treasures.
1. Vin 909 – A Cozy Gem with Big Flavors
Tucked away in Eastport, Vin 909 is the kind of place locals fight to keep secret. This intimate spot serves up wood-fired pizzas and small plates that’ll knock your socks off.
Think crispy crusts, fresh local ingredients, and flavor combos that dance on your tongue. Their farm-to-table approach means every bite tastes like it was made just for you.
The vibe? Rustic, warm, and totally unpretentious—like eating at your coolest friend’s house. Pro tip: Get there early.
This place fills up fast, and for good reason. Whether you’re a pizza fanatic or just love good food, Vin 909 is a must-visit in Annapolis.
2. Chick & Ruth’s Delly – A Legendary Annapolis Institution
If you haven’t been to Chick & Ruth’s Delly, have you even been to Annapolis? This iconic spot has been serving massive sandwiches and hearty breakfasts since 1965.
The menu is packed with comfort food classics—think towering pastrami Reubens, creamy milkshakes, and omelets that could feed a small army.
The best part? The quirky, old-school diner vibe—complete with patriotic pledge recitals every morning. It’s loud, it’s lively, and it’s 100% Annapolis.
Whether you’re craving a stacked sandwich or just want to soak in the local culture, this deli delivers.
3. O’Learys Seafood Restaurant – Fresh Catches & Waterfront Views
For seafood lovers, O’Learys is the holy grail. Located right by the docks, this upscale yet relaxed spot serves the freshest catches in Annapolis. Their crab cakes? Pure perfection—juicy, lumpy, and packed with flavor.
The menu changes with the seasons, but you can always count on buttery lobster tails, seared scallops, and melt-in-your-mouth fish dishes.
Pair it with a waterfront view, and you’ve got yourself a meal to remember. If you want top-tier seafood in Annapolis MD, O’Learys is where it’s at.
4. Iron Rooster – All-Day Breakfast Done Right
Who says breakfast is just for mornings? At Iron Rooster, you can get fluffy pancakes, crispy bacon, and loaded omelets any time of day.
This place is all about comfort food with a creative twist—like their famous “Roostarts” (homemade pop-tarts) or chicken and waffles that’ll make you weak in the knees.
The atmosphere is laid-back and welcoming, making it perfect for lazy weekend brunches or quick weekday bites. If you’re hunting for the best breakfast in Annapolis, Iron Rooster should be at the top of your list.
5. Preserve – Modern Flavors with a Southern Twist
Preserve is where Southern charm meets modern flair. This farm-to-table spot focuses on seasonal ingredients, turning them into dishes that are both familiar and exciting.
Think smoked catfish dip, crispy fried chicken, and desserts that’ll have you licking the plate.
The vibe is elegant but unfussy—great for date night or a fancy dinner with friends. If you want innovative, delicious food in Annapolis, Preserve nails it every time.
Here are 11 more restaurant headings in the same engaging, SEO-optimized style, completing your “15+ Best Restaurants in Annapolis MD” listicle:
6. Carroll’s Creek Café – Waterfront Dining at Its Finest
Overlooking Annapolis Harbor, Carroll’s Creek Café offers stunning views and even better food.
Known for their signature crab dip and perfectly cooked filet mignon, this spot is ideal for a romantic dinner or a classy night out. The seafood is always fresh, the service is impeccable, and that sunset view? Chef’s kiss.
7. Level – A Small Plates Lounge with Big Personality
If you love sharing food (or just want to try a little of everything), Level is your spot.
Their globally inspired small plates—like Korean BBQ tacos and truffle mac & cheese—are perfect for groups. The modern, lounge-like vibe makes it great for date night or a fun dinner with friends.
8. Boatyard Bar & Grill – A Nautical-Themed Seafood Haven
A local favorite, Boatyard Bar & Grill screams Annapolis charm. Their award-winning crab cakes and lobster rolls keep seafood lovers coming back.
The laid-back, maritime-themed décor makes you feel like you’re dining dockside—even if you’re not.
9. Metropolitan Kitchen & Lounge – Upscale Comfort Food
Craving something elevated but cozy? Metropolitan Kitchen & Lounge nails it with dishes like duck confit grilled cheese and braised short ribs.
The speakeasy-style bar adds a touch of vintage cool, making this a great spot for dinner and drinks (minus the alcohol mention, of course).
10. Miss Shirley’s Café – Brunch Like a Boss
Brunch isn’t just a meal at Miss Shirley’s Café—it’s an event. Their famous coconut cream-stuffed French toast and Chesapeake Benedict (with crab cakes, obviously) have made this place a legend.
Go hungry, leave happy.
11. Lemongrass – Thai Cuisine That Packs a Punch
For a flavor explosion, Lemongrass brings authentic Thai taste to Annapolis.
Their pad Thai and green curry are fan favorites, and the veggie options are just as killer. Spice lovers, rejoice—you can crank up the heat to your liking.
12. The Blackwall Hitch – Seafood & Steaks with a View
Right on the water, The Blackwall Hitch serves seafood so fresh it might still be wiggling.
The oyster bar is a must-try, and their steaks? Butter-knife tender. Plus, the rooftop deck offers one of the best views in town.
13. Vida Taco Bar – Street Tacos with a Gourmet Twist
Taco Tuesday? More like Taco Anyday at Vida Taco Bar. Their creative fillings—like crispy avocado and roasted cauliflower—keep things exciting.
The margaritas (oops, scratch that—the agua frescas) are just as refreshing.
14. Bread & Butter Kitchen – Farm-Fresh Sandwiches & More
This charming café is all about simple, high-quality ingredients.
Their sandwiches (like the roasted turkey with cranberry mayo) are next-level, and the baked goods? Worth every calorie.
15. Jalapeños – Mexican Flavors That Hit the Spot
When you need a cheesy, spicy, crunchy fix, Jalapeños delivers.
Their fajitas sizzle, the guac is always fresh, and the vibe is pure fiesta. Bonus: Plenty of vegan-friendly options!
16. Fox’s Den – Gourmet Pizza & Crafted Comfort in Downtown Annapolis
If you’re craving next-level pizza in Annapolis, Fox’s Den is where it’s at. This trendy downtown hotspot slings wood-fired pies with creative toppings that’ll make your taste buds do a happy dance.
Think spicy honey-drizzled pepperoni, truffle mushroom white pizza, and even a killer vegan BBQ jackfruit option.
But it’s not just about pizza—their smash burgers (juicy, crispy-edged perfection) and loaded tater tots are legit meal-worthy too.
The vibe? Industrial-chic meets neighborhood hangout, with exposed brick, warm lighting, and a buzzing energy that makes every visit feel like a night out.
Final Thoughts
From hidden gems to waterfront staples, Annapolis’ food scene is packed with flavor, charm, and unforgettable meals. Whether you’re a seafood fanatic, brunch enthusiast, or just love great food, this list has you covered.
Now go eat your way through Annapolis—you won’t regret it! Got a favorite spot we missed? Drop it in the comments (we’re always hungry for more).