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Dining Review - The Point Crab House
Mom-Mom’s Maryland crab from the Point
Deb Lindsey/for The Washington Post via Getty Images

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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Mom-Mom’s Maryland crab from the Point
| Deb Lindsey/for The Washington Post via Getty Images

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. 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. Be prepared for big crowds the first weekend of October for the annual powerboat show.

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. New additions to the list include the Graduate Hotel, Bitty & Beau’s Coffee, Dangerously Delicious Pies, and Forward Brewing. While many D.C. restaurants have 86ed crabs this summer due to their price increases, many Annapolis restaurants that benefit from proximity to the water are continuing to stock them.

Health experts consider dining out to be a high-risk activity for the unvaccinated; the latest data about the delta variant indicates that it may pose a low-to-moderate risk for the vaccinated, especially in areas with substantial transmission. The latest CDC guidance is here; find a COVID-19 vaccination site here.

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Note: Restaurants on this map are listed geographically.

1. The Point Crab House & Grill

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700 Mill Creek Rd
Arnold, MD 21012
(410) 544-5448
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There’s a healthy debate as to which crab-picking house reigns supreme in Annapolis. This first-come, first-serve venue right on the water in nearby Arnold is a little more refined than Cantler’s — a competitor with a longstanding history — and offers steamed crabs delivered daily by locals. Maryland crab also makes it way into dips and soups, but lump crab cakes haven’t been available this summer.

Dining Review - The Point Crab House
Steamed crabs from the Point
Deb Lindsey/For The Washington Post via Getty Images

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. As of late August, the kitchen was closing at 10 p.m. on weeknights and 11 p.m. on weekends. 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.

Patio seating at Reynold’s Tavern in Annapolis
Patio seating at Reynold’s Tavern in Annapolis
Reynold’s Tavern/Facebook

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 chorizo mac and cheese bites and “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. 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

8. Bitty & Beau's Coffee

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124 Dock St
Annapolis, MD 21401

This growing coffee chain that prides itself on employing people with intellectual and developmental disabilities got its start in Wilmington, North Carolina, in 2016. The Dock Street location debuted in March 2020, and a D.C. outpost is en route to Georgetown.

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. Thursday to Sunday, includes a monkfish gyro, bone-in lamb shoulder chops, and rockfish crudo.

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. All beer and wine is $3.99 all day, and martinis like a State Senate Party Margarita with tequila and cabernet is $6. Due to rising prices, the Delly stopped shipments of jumbo lump crab cakes to anywhere in the U.S. but continues to sling crab cakes in-house. 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. Kitchen on West St.

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174 West St
Annapolis, MD 21401
(410) 990-1100
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This modern, nautical-themed restaurant inside the Hilton Garden Inn downtown runs a steal of a happy hour (weekdays from 4 p.m. to 7 p.m. and all day Sunday). Tall drafts and bottled beers from local brewers like Jailbreak and Heavy Seas are $4 to $5, and flatbreads are $8.

A beer from the Kitchen on West Street
A beer from the Kitchen on West Street
Tierney Plumb/Eater DC

12. 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.

13. Dangerously Delicious Pies

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212 West St
Annapolis, MD 21401
(410) 990-0743
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The popular D.C. and Baltimore pie shop touched down in Annapolis in 2020 with a rotating menu of sweet or savory pies and quiches.

Lemon chess pie from Dangerously Delicious
Dangerously Delicious

14. 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. As of late August, it was sticking with takeout only, including a $49 special on a 8-ounce petit filet with a mashed or baked potato, a choice of a veggie, and dessert.

Lewnes’ Steakhouse/official photo

15. 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.

16. 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 deviled crab rolls, 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.

17. 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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18. 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 Fridays to Sundays (note: it’s closed over Labor Day weekend).

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Tomato Galettes!

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19. 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.

20. 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 strawberry shortcake sundae and eclair brownie.

1. The Point Crab House & Grill

700 Mill Creek Rd, Arnold, MD 21012
Dining Review - The Point Crab House
Steamed crabs from the Point
Deb Lindsey/For The Washington Post via Getty Images

There’s a healthy debate as to which crab-picking house reigns supreme in Annapolis. This first-come, first-serve venue right on the water in nearby Arnold is a little more refined than Cantler’s — a competitor with a longstanding history — and offers steamed crabs delivered daily by locals. Maryland crab also makes it way into dips and soups, but lump crab cakes haven’t been available this summer.

700 Mill Creek Rd
Arnold, MD 21012

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. As of late August, the kitchen was closing at 10 p.m. on weeknights and 11 p.m. on weekends. Tsunami accepts takeout orders over the phone.

51 West St
Annapolis, MD 21401

4. Reynold's Tavern

7 Church Cir, Annapolis, MD
Patio seating at Reynold’s Tavern in Annapolis
Patio seating at Reynold’s Tavern in Annapolis
Reynold’s Tavern/Facebook

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 chorizo mac and cheese bites and “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. 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

8. Bitty & Beau's Coffee

124 Dock St, Annapolis, MD 21401

This growing coffee chain that prides itself on employing people with intellectual and developmental disabilities got its start in Wilmington, North Carolina, in 2016. The Dock Street location debuted in March 2020, and a D.C. outpost is en route to Georgetown.

124 Dock St
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. Thursday to Sunday, includes a monkfish gyro, bone-in lamb shoulder chops, and rockfish crudo.

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. All beer and wine is $3.99 all day, and martinis like a State Senate Party Margarita with tequila and cabernet is $6. Due to rising prices, the Delly stopped shipments of jumbo lump crab cakes to anywhere in the U.S. but continues to sling crab cakes in-house. 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. Kitchen on West St.

174 West St, Annapolis, MD 21401
A beer from the Kitchen on West Street
A beer from the Kitchen on West Street
Tierney Plumb/Eater DC

This modern, nautical-themed restaurant inside the Hilton Garden Inn downtown runs a steal of a happy hour (weekdays from 4 p.m. to 7 p.m. and all day Sunday). Tall drafts and bottled beers from local brewers like Jailbreak and Heavy Seas are $4 to $5, and flatbreads are $8.

174 West St
Annapolis, MD 21401

12. 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

13. Dangerously Delicious Pies

212 West St, Annapolis, MD 21401
Lemon chess pie from Dangerously Delicious
Dangerously Delicious

The popular D.C. and Baltimore pie shop touched down in Annapolis in 2020 with a rotating menu of sweet or savory pies and quiches.

212 West St
Annapolis, MD 21401

14. 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. As of late August, it was sticking with takeout only, including a $49 special on a 8-ounce petit filet with a mashed or baked potato, a choice of a veggie, and dessert.

401 Fourth St
Annapolis, MD 21403

15. 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

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16. 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 deviled crab rolls, 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

17. 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

18. 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 Fridays to Sundays (note: it’s closed over Labor Day weekend).

618 Chesapeake Ave.
Annapolis, MD

19. 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

20. 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 strawberry shortcake sundae and eclair brownie.

1409 Forest Dr
Annapolis, MD 21403

Related Maps