Here’s our list of favorite restaurants, we keep adding and subtracting. We listen closely to our guests as well as go by our own experience….In ALL cases, when you visit/make recommendations, tell them that the Flag House Inn recommended them, you might even get a surprise! (OT= can make reservation on Open Table) (CO = Carryout)
COVID – 19 update – most every place on this list is doing meal and often drink pickup and nearly every restaurant in town has some form of outdoor dining – we can direct you, or call / see their website for info, many require using an app – we can assist
Fine Dining – reservations always recommended, we can assist
Carroll’s Creek – For over 30 years, great seafood overlooking Spa Creek. Take the water taxi to the front door. (Eastport) 410-263-8102 OT
O’Learys – Fantastic seafood with great service served in a venerable old house. (Eastport) 410-263-0884 OT
Lewne’s Steakhouse – Since 1921, they’ve been serving prime steaks & chops with an extensive wine list. Excellent service – Mack & Sam will take care of you! (Eastport) 410-263-1617 OT
Harry Browne’s – Quiet and scenic location on State Circle overlooking the State House. Great emphasis on fresh ingredients. More casual in upstairs bar. 410-263-4332 OT
Cafe Normandie – Fine French bistro on upper Main St. – extensive menu, expert preparation. All the classics. Great comfort food. 410-263-3382 OT
Flamant – West Annapolis, less than 10 min drive. Very foodie, super creative but small menu, great service 410-267-0274 OT
Severn Inn – Across Severn river bridge (450). Fine dining or informal bar. Lovely view across to Annapolis. 410-349-4000 OT
Reynolds Tavern – Historic setting in 1747 tavern – Known for afternoon tea, cellar bar and outdoor garden. Main room food good also! 410-295-9555 OT
Osteria 177 – Fine Italian dining. The veal chop is THE dish for that special event. 410-267-7700 OT
Blackwall Hitch – Extensive menu, big place/many group dinners. Easy walk across bridge to Eastport. 410-263-3454 OT
Chart House – Lovely setting in former boat building factory. Take the water taxi to front door. Better for happy hour or drinks than dinner. 410-268-7166 OT
Ruth’s Chris – Steak Chain Eastport 410-990-0033 OT
Casual
Boatyard – The “Margarittaville ” of Annapolis. Great seafood, reasonably priced, great boat drinks (cocktails), boating atmosphere, loud, fun. Huge outdoor tent makes it an obvious choice. (Eastport). See this article – owner is great guy… No reservations 410-216-6206
Iron Rooster – We aspire to make what they post on Instagram. Southern and breakfast all day. Fresh preparation. Try the home made pop tarts! 410-990-1600 OT
Galway Bay – Our favorite place for a beer/cocktail. Pub serves both the famous Irish brands and local craft beers. Great whiskey bar and the food is great! Check schedule, frequent entertainment. Locals spot on Maryland Ave. 410-263-8333 OT
Preserve – Farm to table, small plates, emphasis pickling/fermentation. Crispy kale! 443-598-6920
Vida Taco Bar – Pick your wrapping – lettuce, corn or flour and fill with 12 unique fillings. Great margaritas too! 443-837-6521
Vin 909 – Great foodie & pizza menu in neighborhood setting. Gets VERY busy, no reservations (Eastport) 410-990-1846
Fox’s Den – Easy to miss along Main St, great cocktails, great pizza. Creative menu. No reservations. 443-808-8991
Latitude 38 – great view of the harbor from the outdoor patio. Great apps… Justin, the GM, has done an amazing job supporting the community during the COVID-19 crisis. 667 204 2282
Dry 85/ Red Red Wine – Cocktail bar (D85) and wine bar (RRW). Light fare, flights. 443-214-5171 (D85) 410-990-1144 (RRW)
Dock St Pub – Top 5 in town for crab cakes, friendly bartenders, local-ish. 410-268-7278
Market House – This is almost a category of it’s own, this is the re-re-renovated house at City Dock. Many counter service options, gelato bar, raw bar, bakery. Great views out to Ego Alley. 443-949-0024 CO
McGarvey’s – Raw bar, great pub fare, good for late night meal. Long time staple. 410-263-5700
Federal House – Big beer selection and extensive menu. Big place but good service and big servings. Market Square 410-268-2576
Joss – great sushi & Asian dishes. Main St 410-263-4688. CO
Nano – Great sushi & Asian dishes as well. Both of these places are good. 410-267-6688 CO
Tarin Thai – Both the usual Pad Thai / curry but also many other options. Dine in or carry out. Dial up your own spice level! 138 Main St. 443-808-8553 CO
Middletown Tavern – Pub fare, upstairs piano bar, live music … been there forever in Market Square 410-263-3323
Davis’ Pub – Far side of Eastport – if we lived in Eastport, we would be there regularly. Comfort food, pub fare, locals spot. 410-268-7432
Harvest – casual wood fired grill right on Market Square. Nice outdoor seating. 410- 280-8686
Mangia – Italian, eat in or Carry Out 410-268-1350
Sakura Cafe – Asian 410-263 0785 CO
O’Briens – Long time spot, outdoor dining 410-268-6288
Pusser’s (Waterfront Hotel) – go for the daytime view 410-626-0004
Forward Brewing – brand new micro brewery in Eastport, we expect to move them way up the rankings once we get there…
West St – a category by itself – worth the walk, many great places
Level – Small plates 410-268-0003 OT
Sailor Oyster Bar – Great happy hour prices, creative small plates. 410-571-5449
Lighthouse Bistro – What a great concept – Light House gives people with employment barriers the opportunity to learn while developing a resume and earning a living wage. And great food too! 410-424-0922 OT
Tsunami – Sushi & Asian 410-990-9868 CO OT
49 West Coffeehouse – See below – multi-purpose neighborhood spot 410-626-9796
Rams Head – Good bar food, obvious spot if heading to Ram’s Head Live. Basement bar w/ live entertainment 410-268-4545 OT
Stan & Joe’s Saloon – Eclectic neighborhood bar. Sports Bar. Big menu 410-263-1993
Metropolitan – Rooftop bar & brunch 410-280-5160 OT
Lemongrass – Thai 410-280-0086
El Toro Bravo – Mexican 410-267-5949
Luna Blu – Seafood/Italian 410-267-9950 OT
Worth the Drive (and it’s a short list!)
Cantler’s – Rated every year as one of the best crab houses in Maryland and for good reason. Nice waterfront location, extensive menu on addition to steamed crabs (crab soup & soft shell sliders are superb). No reservations. 10 min drive. 410-757-1311
Caliente (10-15 min) – Tremendous commitment to the community, great choice of Latin food (Mexican, Salvadoran, Columbian). Pupusas, Chicken with mole, and much much more. (410) 626-1444 Call for reservations. CO
Jalepeno’s – (10-15 min) Tapas? Yeah, got 60 choices. Spanish? Check Cuban? Of course. Always rated top 5 in Annapolis and with good reason. Don’t be deceived by the average looking exterior. 410 266-7580
Kentmorr – 30 minute drive on Kent Island/Eastern Shore. See our blog on this special place
Sandwiches
Bread & Butter Kitchen – Waterfront in Eastport, local and creative preparation. Tremendous commitment to the community. Order online/phone, walk over, sit outside and enjoy the view 410-202-8680 CO
Big Cheese – Overstuffed sandwiches, snacks 410-263-6915 CO
Sofi’s Crepes – Breakfast, lunch or dinner. Mid favorite. 410-990-0929 CO
Chick & Ruth’s Deli – Long time spot, breakfast, famous name sandwiches, 830a pledge of allegiance 410-269-6737 CO
Jimmy John’s – We see their carryout guy many times a day to deliver to USNA. Must be good! 410-280-3561 CO
Potato Valley – Baked potatoes & sandwiches – State Circle 410-267-0902 CO
Coffee
Old Fox Books/ Brown Mustache Coffee – Very cool setting on Maryland Ave., Frequent live music, student hangout. Browse, surf or hang out 410-626-2020
City Dock – Locations Maryland Ave & Market Square – we serve their coffee
49 West – Coffeehouse, Winebar, Jazz club, Dessert, light fare. 410-6269796
That Seattle Chain – Nice setting on Main St.
Ice Cream
There are 5 ice cream shops along Main St., we can highly recommend two of them:
Annapolis Ice Cream Company – Only shop that makes their own ice cream on site. Sources many other restaurants in town. Look for the Penguins!
Red Bean – Take vanilla or chocolate base and add your own selection of flavorings.
