Note: This post contains affiliate links to the products that I use and trust. This means that I might receive a small commission (at no extra cost to you) if you make a purchase using any of my links below. See full disclosure here
Hungry in Annapolis? Whether you’re visiting for a day or lucky enough to call this charming capital home, you’re probably wondering: Where should I eat right now? From fresh crab feasts to creative small plates and decadent desserts, Annapolis knows how to feed you right. This list isn’t just about what’s trendy — it’s about what tastes amazing. Let’s Dig In.
Tabel of Contents
- 1 1. Iron Rooster — All-Day Brunch Heaven
- 2 2. Preserve — Modern American with a Fermented Flair
- 3 3. Vin 909 — Wood-Fired Pizza & Wine in Eastport
- 4 4. Boatyard Bar & Grill — Where Locals Go for Crab
- 5 5. Chick & Ruth’s Delly — Quirky, Classic, and Full of Heart
- 6 6. Blackwall Hitch — Waterfront Dining with a View
- 7 7. Lemongrass — Thai Food with a Kick
- 8 8. Mason’s Famous Lobster Rolls — New England Taste, Maryland Heart
- 9 Eat Your Way Through Annapolis
1. Iron Rooster — All-Day Brunch Heaven
Ever wish brunch lasted all day? At Iron Rooster, it does. Famous for its giant homemade Pop-Tarts and chicken & waffles, this place nails comfort food with a local twist. Located near City Dock, it’s a must-stop before a day of exploring.

Pro Tip: Weekends get busy — go early or aim for a weekday morning.
2. Preserve — Modern American with a Fermented Flair
Into pickles? Then you’ll love Preserve, a cozy spot on Main Street turning preserved veggies into menu stars. Expect seasonal dishes, craft cocktails, and a fresh spin on Mid-Atlantic flavors. Think: roasted beets, sauerkraut pierogis, and ricotta gnocchi.

Pro Tip: Make a reservation — the space is small, but the flavor is big.
3. Vin 909 — Wood-Fired Pizza & Wine in Eastport
Cross the Spa Creek Bridge into Eastport and discover Vin 909, a cozy bungalow turned wood-fired pizza haven. Their farm-to-table menu changes daily, and the wine list is just as thoughtful. Great for date nights or a casual foodie hangout.
Pro Tip: No reservations here — arrive early or expect a short wait (totally worth it).
4. Boatyard Bar & Grill — Where Locals Go for Crab
This spot is pure Annapolis: nautical decor, boat shoes, and World’s Best Crab Cake Dinner. Sailors and locals love the Boatyard Bar & Grill for its laid-back vibe and standout crab cakes. It’s Maryland, so trust the crab.

Pro Tip: Grab a local beer or Orange Crush to wash it all down.
5. Chick & Ruth’s Delly — Quirky, Classic, and Full of Heart
Come for the kitschy vibe, stay for the massive milkshakes and towering sandwiches. Chick & Ruth’s is a longtime Annapolis institution that feels like stepping into a retro sitcom — in the best way.

Pro Tip: Check out their daily Pledge of Allegiance tradition around 8:30 AM.
6. Blackwall Hitch — Waterfront Dining with a View
Blackwall Hitch nails the vibe for upscale dining with gorgeous water views. The seafood is fresh, the cocktails are classy, and live music often sets the mood. Ideal for a fancier night out or celebration dinner.

Pro Tip: Ask for a table on the deck for prime sunset views.
7. Lemongrass — Thai Food with a Kick
Need a break from crab cakes? Try Lemongrass, Annapolis’s go-to Thai restaurant. With bold curries, crispy spring rolls, and tangy pad Thai, it’s a flavorful detour from typical tourist fare.
Pro Tip: Great for takeout too — grab a curry and picnic at the waterfront.
8. Mason’s Famous Lobster Rolls — New England Taste, Maryland Heart
This fast-casual favorite brings Maine’s famous lobster rolls to Maryland. Mason’s doesn’t overdo it — just buttery rolls, fresh lobster, and simple sides. Perfect for a quick but unforgettable lunch.

Pro Tip: Skip the line and order online for pick-up, then take the food to nearby Ego Alley to eat with a view.
Eat Your Way Through Annapolis
Annapolis might be small, but its food scene packs a punch. Whether you’re craving comfort food, global flavor, or dockside seafood, this city’s a seat waiting for you. Bookmark this list, bring your appetite, and maybe wear stretchy pants (just saying).
Which spot are you dying to try? Share your favorite local eats in the comments or tag your food pics with #AnnapolisBites—I’d love to see what’s on your plate.
Stay curious, stay hungry, and keep exploring!