Flag House Inn

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Restaurants near our Annapolis Inn Bed and Breakfast

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 nearly every restaurant in town has some form of outdoor dining

Fine Diningreservations always recommended, we can assist

Carroll’s Creek – For over 30 years, great seafood, best view of Spa Creek/Harbor.  Both indoor and outdoor dining. Take the water taxi to the front door.  (Eastport) 410-263-8102 OT

O’Learys – Fantastic/Creative/Original seafood dishes 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

Osteria 177 – Fine Italian dining.  The veal chop is THE dish for that special event. 410-267-7700 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

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

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


Boatyard –  The “Margaritaville ” 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/ friendly bartenders serve both the famous Irish brands and local craft beers. Great whiskey bar and the food is great!  Check schedule, frequent entertainment.  Locals spot. Maryland Ave. 410-263-8333 OT

Preserve – Farm to table, small plates, emphasis pickling/fermentation. Most foodie place downtown. Crispy kale! 443-598-6920

Officers Club – USNA (Lunch only M-F) – great food, lovely setting, reasonable prices. Pair with walking tour and USNA museum.

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

Forward Brewing – brand new micro brewery in Eastport, Great light food and the beer is very inventive… Neighborhood spot….

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

Federal House – Big beer selection and extensive menu.  Big place but good service and big servings. Market Square 410-268-2576

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

Market House (Lunch/snack)- 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

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

1771 Grill & Taproom – casual wood fired grill right on Market Square.  Nice outdoor seating.  410- 280-8686

Latitude 38 – great view of the harbor from the outdoor patio.  Great apps. 667 204 2282

O’Briens – Long time spot, outdoor dining 410-268-6288

Pusser’s (Waterfront Hotel) –  go for the daytime drinks & view  410-626-0004

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


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

Pip’s Dock St Dogs – Best cheese steaks this side of Philly ..”Whiz Wit”! Awesome fries and great hot dogs. Locals fave for carry out lunch. 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

Mission BBQ – great support to armed forces and decent BBQ, dine in or 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


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

Bitty & Beau’s – what a great story – great coffee and dedicated staff, run by people with intellectual and developmental disabilities. You will feel great all day having gone there.

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.  Get ready to debate and defend your fave vs ours!

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