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Bright red beet gazpacho
Beet gazpacho at European bistro Flamant.
Flamant/Facebook

Where to Eat and Drink in Annapolis, Maryland

Head to the bayside capital city for a taste of Chesapeake crab, preserve-packed New American cooking, and historic inn fare

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Beet gazpacho at European bistro Flamant.
| Flamant/Facebook

With postcard-perfect views of the Chesapeake Bay and a constant parade of United States Naval Academy midshipmen marching around in dress whites, Annapolis, Maryland, is an idyllic capital city full of prime dining options and iconic crab houses like Cantler’s and The Point, plus Baltimore’s Choptank coming soon. The historic town is located about 30 miles away from the District, making it a roughly 45-minute drive up U.S. 50 East (on a good day). For those wanting to leave the car at home, Maryland Transit runs a convenient bus line for a few bucks near Union Station.

This map highlights a few standbys in the quaint downtown district, but some of the best cafes, bakeries, and restaurants are actually located in Eastport — a quick walk across the bridge.

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Note: Restaurants on this map are listed geographically.

1. Flamant

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17 Annapolis St
Annapolis, MD 21401
(410) 267-0274
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Chef/owner Frederik de Pue of downtown D.C.’s new bistro The Henri also is behind this stylish and homey Annapolis favorite of Washington Post food critic Tom Sietsema. Dine with the seasons with creative dishes like escargot doughnuts, seared scallops, spring lamb, and cotton cake (aka fluffy cheesecake).

2. Galway Bay Irish Restaurant and Pub

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63 Maryland Ave
Annapolis, MD 21401
(410) 263-8333
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This historic Irish pub, located in a cobblestone alleyway steps from State Circle, is known for $6 Guinness pours and hearty food like corned beef poppers and Irish curry fries. The local mainstay refreshed and expanded its bar area, adding colorful stained glass and encased collections of Drumshanbo Gunpowder Irish Gin.

Galway Bay Irish restaurant and Pub in Annapolis Tierney Plumb/Eater DC

3. Tsunami

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51 West St
Annapolis, MD 21401
(410) 990-9868
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This late-night staple slings sushi rolls, rice bowls, steamed buns, and Sriracha-splashed mac and cheese, all complemented by a lengthy beer list. Rotating art exhibits inside support local up-and-comers. Tsunami accepts takeout orders over the phone.

Sushi from Tsunami
Sushi from Tsunami
Tierney Plumb/Eater DC

4. Reynold's Tavern

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7 Church Cir
Annapolis, MD
(410) 295-9555
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The tavern was built across from St. Anne’s Church in 1747, so dining here doubles as a history lesson. Soak up with last days of summer across an outdoor brick patio strung with overhead lights that hosts rotating trivia and live acoustic nights. Afternoon tea service runs daily from 11 a.m. to 5 p.m.

5. Iron Rooster (Multiple locations)

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12 Market Space
Annapolis, MD
(410) 990-1600
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This bustling spot serves breakfast all day, but “waffle” burgers are also a hit. Walk off protein-packed omelets, crab Benedict, and creamy grits by wandering to the water to take in the natural beauty of the surrounding harbor. A morning weekday happy hour (8 a.m. to 10 a.m.) caters to Ernest Hemingway types with $6 bacon bloody marys.

6. The Trophy Room

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126 West St
Annapolis, MD 21401
(410) 263-7777
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Tucked inside Annapolis’s preppy new Graduate Hotel, the Trophy Room’s playful bar menu includes snacks like pimento cheese and pepper jelly Ritz crackers, an “Adult Capri Sun” spiked with vodka, and Jell-o shots. The hotel’s Poindexter cafe fuels up guests with hot breakfast sandwiches, coffee from Coffee Manufactory, and oatmeal.

The Trophy Room

7. Level a small plates lounge

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69 West St
Annapolis, MD 21401
(410) 268-0003
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Fried Brussels sprouts and spicy tuna tartare are favorites at this lounge devoted to small plates designed for sharing. The globally-influenced plates go well with a cocktail: the long list includes a lime foam-topped gimlet and tropical white sangria.

8. Drummer’s Lot

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16 Church Cir
Annapolis, MD 21401
(410) 216-6340
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Tucked under the historic 18th-century Maryland Inn, English pub Drummer’s Lot starts pouring after 5 p.m. at the top of Church Circle. The hidden, brick-lined bar is known for its burgers and beers. Its 1920s-themed, luxe sister bar Harry Browne’s overlooks the Maryland State House and has served American cuisine and wines to local politicians and lobbyists for generations.

Drummer’s Lot/official photo

9. Preserve

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164 Main St
Annapolis, MD
(443) 598-6920
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This New American restaurant serves canned, pickled, and fermented produce, all with prime people-watching just off Main Street. The all-day menu, available 11 a.m. to 9 p.m. Wednesday to Sunday, includes a smoked fish dip, fried duck tongues, bucatini with Virginia clams, and lamb gyros.

Preserve/official photo

10. Chick & Ruth's Delly

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165 Main St
Annapolis, MD 21401
(410) 269-6737
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This family-owned greasy spoon has served all-day breakfast to countless politicians and celebrities since 1965. The Delly ships jumbo lump crab cakes across the U.S. and slings crab cakes in-house. All beer and wine is $3.99 all day. Past governors, judges, senators and delegates get their own sandwich names at the patriotic diner, where the National Anthem is recited every morning.

The facade at Chick & Ruth’s
The facade at Chick & Ruth’s
Tierney Plumb/Eater DC

11. Sailor Oyster Bar

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196 West St #2824
Annapolis, MD 21401
(410) 571-5449
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This hip oyster bar has tinned fish, crudo, toasts, and $1 local oysters during happy hour (Tuesday through Friday from 4 p.m. to 5:30 p.m.). The bar shows lots of love for D.C. spirits, with Ivy City’s Civic Vodka and One Eight distilling in the mix.

12. Lewnes' Steakhouse

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401 Fourth St
Annapolis, MD 21403
(410) 263-1617
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This 1920s-era steakhouse, adorned with high-back booths, white tablecloths, and vintage photos, is the crown jewel surf-and-turf option in Eastport. The classic menu includes cuts like porterhouse and filet mignon, clams casino, jumbo lump crab balls, and sides like creamed spinach or mashed potatoes.

Lewnes’ Steakhouse/official photo

13. Boatyard Bar & Grill

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400 Fourth St
Annapolis, MD
(410) 216-6206
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This airy waterfront spot is surrounded by broken shells and designed to look like the interior of a boat. Self-proclaimed fans of the filler-free crab cakes here include legendary Baltimore Orioles infielder Cal Ripken Jr. and musician Jimmy Buffet.

14. Forward Brewing

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418 Fourth St
Annapolis, MD 21403
(443) 221-7277
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Annapolis’s first “nanobrewery” opened right before the pandemic, serving cans, pints, and crowlers of beer brewed in the back. Options include an “Annapolis Boat” kölsch-style ale and a “Ceremonious Exchange” imperial porter made with cold brew from Annapolis-based Ceremony Roasters. The diverse food menu includes chicken tinga tacos, build-your-own meat and cheese boards, and a smoked fish spread. Sit inside the stark white space or saddle up to a stone-filled patio.

15. Davis' Pub

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400 Chester Ave
Annapolis, MD
(410) 268-7432
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This long-standing neighborhood pub, packed into a tiny wood cabin, sits right by the water and is famous for crab cake pretzels that were featured on Guy Fieri’s Diners, Drive-Ins, and Dives. Expect to brush shoulders with exuberant yacht owners downing frosty Loose Cannon beers.

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A perfect night awaits you at the pub

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16. Bakers & Co.

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618 Chesapeake Ave.
Annapolis, MD
(410) 280-1119
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This small, family-owned bakery and cafe rolls out an impressive lineup of pastries and breads. Pre-order online for pickup on Saturdays and Sundays. Its carbs also make an appearance at the Anne Arundel County Farmers’ Market on Saturday mornings.

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Tomato Galettes!

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17. Vin 909

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909 Bay Ridge Ave
Annapolis, MD
(410) 990-1846
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Located in a cozy, self-styled “winecafe,” Vin 909 is known for gourmet pizzas and a seasonal menu. To alleviate long wait times, there’s a “living room” area where visitors can enjoy wines — by the glass or bottle — before sitting down to dinner.

18. Bruster's Real Ice Cream

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1409 Forest Dr
Annapolis, MD 21403
(410) 295-0025
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This family-owned business makes all of its own ice creams, waffle cones and bowls, and Italian ices on-site. Seasonal concoctions include a sea salt caramel and eclair brownie.

1. Flamant

17 Annapolis St, Annapolis, MD 21401

Chef/owner Frederik de Pue of downtown D.C.’s new bistro The Henri also is behind this stylish and homey Annapolis favorite of Washington Post food critic Tom Sietsema. Dine with the seasons with creative dishes like escargot doughnuts, seared scallops, spring lamb, and cotton cake (aka fluffy cheesecake).

17 Annapolis St
Annapolis, MD 21401

2. Galway Bay Irish Restaurant and Pub

63 Maryland Ave, Annapolis, MD 21401
Galway Bay Irish restaurant and Pub in Annapolis Tierney Plumb/Eater DC

This historic Irish pub, located in a cobblestone alleyway steps from State Circle, is known for $6 Guinness pours and hearty food like corned beef poppers and Irish curry fries. The local mainstay refreshed and expanded its bar area, adding colorful stained glass and encased collections of Drumshanbo Gunpowder Irish Gin.

63 Maryland Ave
Annapolis, MD 21401

3. Tsunami

51 West St, Annapolis, MD 21401
Sushi from Tsunami
Sushi from Tsunami
Tierney Plumb/Eater DC

This late-night staple slings sushi rolls, rice bowls, steamed buns, and Sriracha-splashed mac and cheese, all complemented by a lengthy beer list. Rotating art exhibits inside support local up-and-comers. Tsunami accepts takeout orders over the phone.

51 West St
Annapolis, MD 21401

4. Reynold's Tavern

7 Church Cir, Annapolis, MD

The tavern was built across from St. Anne’s Church in 1747, so dining here doubles as a history lesson. Soak up with last days of summer across an outdoor brick patio strung with overhead lights that hosts rotating trivia and live acoustic nights. Afternoon tea service runs daily from 11 a.m. to 5 p.m.

7 Church Cir
Annapolis, MD

5. Iron Rooster (Multiple locations)

12 Market Space, Annapolis, MD

This bustling spot serves breakfast all day, but “waffle” burgers are also a hit. Walk off protein-packed omelets, crab Benedict, and creamy grits by wandering to the water to take in the natural beauty of the surrounding harbor. A morning weekday happy hour (8 a.m. to 10 a.m.) caters to Ernest Hemingway types with $6 bacon bloody marys.

12 Market Space
Annapolis, MD

6. The Trophy Room

126 West St, Annapolis, MD 21401
The Trophy Room

Tucked inside Annapolis’s preppy new Graduate Hotel, the Trophy Room’s playful bar menu includes snacks like pimento cheese and pepper jelly Ritz crackers, an “Adult Capri Sun” spiked with vodka, and Jell-o shots. The hotel’s Poindexter cafe fuels up guests with hot breakfast sandwiches, coffee from Coffee Manufactory, and oatmeal.

126 West St
Annapolis, MD 21401

7. Level a small plates lounge

69 West St, Annapolis, MD 21401

Fried Brussels sprouts and spicy tuna tartare are favorites at this lounge devoted to small plates designed for sharing. The globally-influenced plates go well with a cocktail: the long list includes a lime foam-topped gimlet and tropical white sangria.

69 West St
Annapolis, MD 21401

8. Drummer’s Lot

16 Church Cir, Annapolis, MD 21401
Drummer’s Lot/official photo

Tucked under the historic 18th-century Maryland Inn, English pub Drummer’s Lot starts pouring after 5 p.m. at the top of Church Circle. The hidden, brick-lined bar is known for its burgers and beers. Its 1920s-themed, luxe sister bar Harry Browne’s overlooks the Maryland State House and has served American cuisine and wines to local politicians and lobbyists for generations.

16 Church Cir
Annapolis, MD 21401

9. Preserve

164 Main St, Annapolis, MD
Preserve/official photo

This New American restaurant serves canned, pickled, and fermented produce, all with prime people-watching just off Main Street. The all-day menu, available 11 a.m. to 9 p.m. Wednesday to Sunday, includes a smoked fish dip, fried duck tongues, bucatini with Virginia clams, and lamb gyros.

164 Main St
Annapolis, MD

10. Chick & Ruth's Delly

165 Main St, Annapolis, MD 21401
The facade at Chick & Ruth’s
The facade at Chick & Ruth’s
Tierney Plumb/Eater DC

This family-owned greasy spoon has served all-day breakfast to countless politicians and celebrities since 1965. The Delly ships jumbo lump crab cakes across the U.S. and slings crab cakes in-house. All beer and wine is $3.99 all day. Past governors, judges, senators and delegates get their own sandwich names at the patriotic diner, where the National Anthem is recited every morning.

165 Main St
Annapolis, MD 21401

11. Sailor Oyster Bar

196 West St #2824, Annapolis, MD 21401

This hip oyster bar has tinned fish, crudo, toasts, and $1 local oysters during happy hour (Tuesday through Friday from 4 p.m. to 5:30 p.m.). The bar shows lots of love for D.C. spirits, with Ivy City’s Civic Vodka and One Eight distilling in the mix.

196 West St #2824
Annapolis, MD 21401

12. Lewnes' Steakhouse

401 Fourth St, Annapolis, MD 21403
Lewnes’ Steakhouse/official photo

This 1920s-era steakhouse, adorned with high-back booths, white tablecloths, and vintage photos, is the crown jewel surf-and-turf option in Eastport. The classic menu includes cuts like porterhouse and filet mignon, clams casino, jumbo lump crab balls, and sides like creamed spinach or mashed potatoes.

401 Fourth St
Annapolis, MD 21403

13. Boatyard Bar & Grill

400 Fourth St, Annapolis, MD

This airy waterfront spot is surrounded by broken shells and designed to look like the interior of a boat. Self-proclaimed fans of the filler-free crab cakes here include legendary Baltimore Orioles infielder Cal Ripken Jr. and musician Jimmy Buffet.

400 Fourth St
Annapolis, MD

14. Forward Brewing

418 Fourth St, Annapolis, MD 21403

Annapolis’s first “nanobrewery” opened right before the pandemic, serving cans, pints, and crowlers of beer brewed in the back. Options include an “Annapolis Boat” kölsch-style ale and a “Ceremonious Exchange” imperial porter made with cold brew from Annapolis-based Ceremony Roasters. The diverse food menu includes chicken tinga tacos, build-your-own meat and cheese boards, and a smoked fish spread. Sit inside the stark white space or saddle up to a stone-filled patio.

418 Fourth St
Annapolis, MD 21403

15. Davis' Pub

400 Chester Ave, Annapolis, MD

This long-standing neighborhood pub, packed into a tiny wood cabin, sits right by the water and is famous for crab cake pretzels that were featured on Guy Fieri’s Diners, Drive-Ins, and Dives. Expect to brush shoulders with exuberant yacht owners downing frosty Loose Cannon beers.

400 Chester Ave
Annapolis, MD

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16. Bakers & Co.

618 Chesapeake Ave., Annapolis, MD

This small, family-owned bakery and cafe rolls out an impressive lineup of pastries and breads. Pre-order online for pickup on Saturdays and Sundays. Its carbs also make an appearance at the Anne Arundel County Farmers’ Market on Saturday mornings.

618 Chesapeake Ave.
Annapolis, MD

17. Vin 909

909 Bay Ridge Ave, Annapolis, MD

Located in a cozy, self-styled “winecafe,” Vin 909 is known for gourmet pizzas and a seasonal menu. To alleviate long wait times, there’s a “living room” area where visitors can enjoy wines — by the glass or bottle — before sitting down to dinner.

909 Bay Ridge Ave
Annapolis, MD

18. Bruster's Real Ice Cream

1409 Forest Dr, Annapolis, MD 21403

This family-owned business makes all of its own ice creams, waffle cones and bowls, and Italian ices on-site. Seasonal concoctions include a sea salt caramel and eclair brownie.

1409 Forest Dr
Annapolis, MD 21403

Related Maps