Annapolis is one of my favorite food towns in Maryland, so I finally pulled together a guide to the best restaurants in the area. This list covers a whole lot of ground, from a farm-to-table gem on Main Street to loaded hot dogs right on the water at City Dock, a Southern kitchen worth the drive to Parole, and a charming afternoon tea experience. Whether you’re after a nice date-night dinner, a quick waterfront lunch, a cozy cafe breakfast, or a big group spread, there’s something here for the occasion.
A good chunk of these are right in the historic downtown or just across the bridge in Eastport, so you can easily string a few together into one great food day. They’re in no particular order (I love them all for different reasons), and I’ve flagged where you’ll want a reservation or to arrive early. So whether you’re visiting for the weekend or you’re a local looking to shake up your rotation, grab your crew, Nomsters, and let’s eat our way through Annapolis.
Jump to a restaurant
1. Carlson’s
Carlson’s might be the best Thai food in Annapolis, no cap, and it’s one of the spots I always tell people about first. On West Street, it’s a Thai kitchen by night and a donut bakery by day, which is a combo you just don’t see often. The Drunken Noodles ($14.29) with beef are perfectly chewy and loaded with veggies, the Gaeng Key Wan green curry ($15.79) is packed with eggplant, peppers and basil, and the Kratim Pik Thai ($14.99), stir-fried chicken with black pepper and garlic, was a surprise favorite.
Fair warning, the food runs hot, so just ask for it milder if fiery isn’t your thing. The ambiance isn’t really the draw, the standout service and spotless dining room are, and honestly the food speaks for itself. Oh, and do not skip the donuts, their Boston cream and apple fritter are a must if you swing by in the morning (the bakery and kitchen keep different hours, so check before you go).
📍1022 West St, Annapolis, MD
2. Annapolis Ice Cream Company
No Annapolis food day is complete without ice cream, and this is the family to get it from. I actually reviewed their West Annapolis sister shop, Always Ice Cream Company, run by the same folks (the Cohens) behind the beloved Annapolis Ice Cream Company downtown, so either way you’re getting the good stuff. They make everything in house with real ingredients (the strawberry uses actual blended strawberries), and rotate through well over 200 flavors, so there’s always something new to try.
My mom and I did a double scoop ($5.85) of peach and apple pie that were both AMAZING, but the showstopper was the Nutty Buddy ($6), which she raved about for literal days afterward, so do not leave without one! Pints run $7.30 if you want to take the party home. The West Annapolis shop is bright, minimalist and super cute, and it’s an easy, feel-good treat whether you’re with family or flying solo.
📍116 Annapolis St, Annapolis, MD
3. Preserve
Some spots get hyped so much you brace for a letdown, but Preserve actually earns every bit of the buzz. Right on Main Street a few blocks from the water, it’s a farm-to-table restaurant built around fermentation and pickling, so familiar comfort dishes come out a little funky and bright in the best way.
The Cheddar Pierogies tossed with Swiss chard kimchi are a perfect pillowy-meets-tangy starter, the pan roasted rockfish (my mom’s favorite) came out flaky and impeccably cooked, and the tiramisu crepe cake at the end is a total showstopper, so save room, I mean it!
Chef-owner Jeremy Hoffman trained at the CIA, and Washingtonian named Preserve one of its 100 Very Best Restaurants for 2026. You can even take home jars of their house ferments (kimchi, curtido, sauerkraut) under the Cabbage Alley label. It’s my pick for a thoughtful date night or a lingering lunch with someone who actually cares about food.
📍164 Main St, Annapolis, MD
4. Giolitti Deli
If you love a proper old-school Italian deli, Giolitti’s is a must. It’s been an Annapolis fixture since 1992, and it’s part sandwich counter, part full-on Italian market, so you come for a sub and leave with imported cheese, frozen pasta and a bottle of wine (they have SO much to choose from).
The Build Your Own sandwich (half $5.95, full $9.95) was my favorite, I did prosciutto, fresh mozzarella, tomato and balsamic on super soft focaccia, and they’re really generous with the meat. The Porchetta (half $8.95) leans more garlic-heavy on a very crispy baguette, so order it if you like bold, crunchy bites.
For dessert, the mini cannoli ($2.25) is cute, but the tiramisu ($5.95) is the real winner, a big, generous portion for the price, so if you only get one, make it that! Everything’s made to order, so call ahead at busy times, and there’s free parking on site. I’m already going back for that lasagna.
📍2068 Somerville Rd, Annapolis, MD
5. Chick & Ruth’s
Chick & Ruth’s Delly is an Annapolis institution, the kind of classic diner everyone keeps telling you to go to, and it lives up to the hype. It’s been a Main Street fixture forever, got featured on Man v Food, and the milkshakes alone are a sight to behold.
I had to try their famous Crab Cake Platter ($29.99), a huge, flavorful cake that comes with two sides and a roll (the coleslaw was excellent, the crab mac not my jam). The Senator Ben Cardin Reuben ($11.99) is solid, just know none of their sandwiches come with sides.
Where they really shine is the from-scratch baked goods, the apple pie a la mode (ask them to heat it and add a scoop of ice cream) was fantastic, and the black and white cookie was pure heaven. The booths run a little cozy, so you might feel squished on a busy day, but the warm hospitality makes you want to come right back. A proper old-school stop downtown.
📍165 Main St, Annapolis, MD
6. Reynold’s Tavern
For something a little different in Annapolis, Reynold’s Tavern does a wonderful afternoon tea, and my mom and I had the best time. We went with the Colonial High Tea ($31 per person), which comes with your pick of loose leaf tea (there’s a LOT to choose from, and they’ll happily swap it if it’s not your thing), a soup or quiche, and a gorgeous tiered tray of savory bites, scones and sweets.
The cream of crab was delicious, and the tray’s little cucumber sandwich, wild mushroom tart, pound cake and chocolate truffle were each perfection. Quick heads up if you’re not into oregano, the French onion leans heavy on it. The Lili’uokalani tea, a fruity house bestseller with peach, mango and guava notes, was a lovely pick. Between the impeccable service and the inviting, historic setting, it’s such a charming thing to do with your mom, a friend, or anyone who loves a proper tea service. Tea runs 11 to 5 daily.
📍 7 Church Cir, Annapolis, MD
7. Vin 909 Winecafé
Vin 909 Winecafe sits in a cozy little cottage in Eastport, right across the bridge from downtown, and it’s one of the most charming farm-to-table spots I’ve been to in a while. They source local produce, run as a zero food waste restaurant, and the menu rotates with the seasons, plus there are 40-plus wines by the glass.
The Wildflowers and Gnocchi ($16), house-made Idaho potato dumplings with grilled local squash and roasted garlic, was the sleeper hit of the whole lunch, sublime is the word I used and I stand by it. The Coconut Shrimp ($18) with a napa and green papaya slaw nails that sweet-and-savory balance, and they’re known for their brick-oven pizzas (the Gnome’s Feast, $21, was a tad salty for us but still yummy).
The space feels like a friend’s homey cottage, with a patio out back, perfect for a chill lunch or low-key date night. They don’t take reservations, so get there early, especially for dinner.
📍 909 Bay Ridge Ave, Annapolis, MD
8. Bread and Butter Kitchen
When you want breakfast on the water in Annapolis, Bread and Butter Kitchen is the move, and I’m still dreaming about a single biscuit because of it. This woman and veteran owned cafe sits right on the water in Eastport, run by Air Force veteran Monica Alvarado, and it makes most everything from scratch with local ingredients.
The buttermilk Biscuit and Jam ($4) with local pineapple jam is the thing I can’t stop thinking about, a total no-brainer add-on, and the Veggie Omelette ($12.29) is a solid, loaded start to the day. Their scones are apparently legendary with flavors that rotate daily, so that’s what I’m going back for.
You can eat with an actual waterfront view, dogs are welcome on the patio, and you can even pull up by boat and tie off at the dock. Breakfast and lunch are served all day, so there’s no rushing to beat a cutoff. The whole place feels genuinely warm, a 10/10 for me.
📍 303 Second St A, Annapolis, MD
9. Julep Kitchen & Bar
Annapolis has no shortage of seafood, so a Southern kitchen this dialed-in is a different kind of treat. Julep in the Parole area is the sister spot to The Hideaway and Buck Murphy’s, and the smoked fried chicken ($22) is reason enough to make the drive.
It’s smoked over pecan wood for three hours before frying, comes as a whole breast, thigh, wing and drumstick, and you slather it in their MVP blackberry chipotle sauce. Start with the 2 Biscuits ($7), which came out PIPING hot with honey butter and pepper jelly, so start there!
The Fried Green Tomatoes ($13) topped with fried shrimp are a beautiful way to kick things off too. The Shrimp and Grits ($24) is really solid even if the chicken steals the show, and the Apple Crisp ($9) is a yum finish. There’s a deep bourbon list, a patio, Sunday brunch, and best of all easy free parking in the plaza, which is a real win in Annapolis. For big, hearty Southern plates, this is my pick.
📍2207 Forest Dr, Annapolis, MD
10. Fox’s Den
Fox’s Den is tucked into a basement beneath Main Street (look for 179B), which gives it this cozy, almost speakeasy feel, and it’s easily one of my favorite pizza spots in Maryland. The Fox brothers handcraft everything from scratch, but the sleeper hit is the Smoked Carrots ($12), rainbow carrots in a chili maple glaze with chili crunch and garlic lime cream cheese, sweet, spicy and tangy all at once, and the portion’s HUGE for twelve bucks!
The Pepperoni and Pepperoncini pizza ($19) is a 10/10 pie, so cheesy with that blistered wood-fired dough and a briny pepperoncini kick I’m still thinking about. The Stuffed Shells ($15) with pork ragu were tasty but not my top pick (those carrots won, lol). There’s serious craft beer, a deep whiskey list, and a barrel-aged cocktail program, so it’s a real gastropub. We went on a random Wednesday and it still packed out, so grab a reservation, especially on weekends. A great cozy downtown dinner.
📍179B Main St, Annapolis, MD
11. The Big Cheese
The Big Cheese is a tiny gourmet sandwich shop and specialty market on Randall Street near City Dock, and it’s exactly the quick, really good lunch you want while wandering downtown. The move is the Annapolitan ($11.50), oven roasted turkey with Granny Smith apple, brie and honey mustard on multigrain, where every single ingredient pulls its weight, a must-order I’d grab again in a heartbeat.
The Fresh Mozzarella and Tomato ($11) was a solid classic, though next time I’m reaching for the Mozzarella and Prosciutto version instead. Beyond sandwiches, it’s part gourmet grocery with 60-plus cheeses, a wall of hot sauces, wine and snacks, so you can grab a whole picnic or a last-minute hostess gift. Just know there’s no seating, it’s grab-and-go, so I ate in my car like a total goblin, lol, though you could easily carry it down to the water. Heads up, menu prices are cash prices, so paying by card might run you a touch more.
📍47 Randall St, Annapolis, MD
12. Pip’s Dock Street Dogs
If you’re near City Dock and not stopping at Pip’s Dock Street Dogs, you’re doing it wrong, I love, love, LOVE this place. It’s a tiny hot dog stand right on Dock Street that’s been a downtown fixture for about 17 years, using natural-casing all-beef Sabrett and Hebrew National dogs with a toppings bar that runs from sweet peppers to house-made Pip’s Relish and 20-plus mustards.
My standout was The Stavvy ($8.55), a spicy dog piled with sharp white cheddar, homemade chili, chipotle mayo and fried onions, all those flavors working together instead of fighting each other. The rotating Reuben Dog special with a ton of sauerkraut was juicy and great, and the Coney Island ($6.25) is their number one seller for a reason (mine came plain by mistake, so it’s next on my list).
They even do Field Roast and Tofurky dogs on vegan buns. After surviving the 2024 floods with community support, this little spot has my whole heart, and the waterfront setting makes a quick lunch feel like an event.
📍118 Dock St, Annapolis, MD
And that’s my running guide to must-try restaurants in Annapolis, and it’s only going to keep growing, there’s always another spot in this town worth the drive. A lot of these pair perfectly together, so don’t be afraid to build a whole day around the water.
Have you guys been to any of these yet, or is there an Annapolis gem I need to try next? Let me know in the comments, Nomsters, and send this to whoever you’d happily split a sandwich (and a scoop of ice cream) with. Save it for your next trip to the water!