Where to Eat in Annapolis: The Best Restaurants and Bars

April 14, 2018 Janette Largent

With more surviving 18th century buildings than any other city in the United States, visiting Annapolis is like stepping back in time to the days when the city was a colonial seaport. Known as America’s Sailing Capital, the city is located on the shores of the Chesapeake Bay and is a paradise for water lovers, famous for its crab cakes, lighthouses, and 500 miles of gorgeous shoreline. Tour the campus of the US Naval Academy, or the Maryland State House, the oldest state capitol still in use.
Things to do in Annapolis

1. Vin 909 Winecafe

909 Bay Ridge Ave, Annapolis, MD 21403-3029 Outdoor Seating, Seating, Waitstaff, Parking Available, Street Parking, Free Off-Street Parking, Wheelchair Accessible, Serves Alcohol, Wine and Beer, Accepts Credit Cards American, Pizza, Wine Bar, Vegetarian Friendly, Vegan Options, Gluten Free Options Lunch, Dinner, Late Night SGD 20 - SGD 52 +1 410-990-1846
Excellent
75%
Good
20%
Satisfactory
3%
Poor
1%
Terrible
1%
Overall Ratings

4.5 based on 603 reviews

Vin 909 Winecafe

Reviewed By Lauren M

We love their imaginative pizzas and combinations, including butternut squash with goat cheese and prosciutto. Great fresh salads to start and excellent wine choices, including a $5/glass (during lunch?) Be ready for a wait or better yet go very early- as soon as they open -or late, at the end of the night.

2. Jalapeno's

85 Forest Drive, Forest Plaza, Annapolis, MD 21401-3716 Takeout, Reservations, Seating, Waitstaff, Parking Available, Wheelchair Accessible, Serves Alcohol, Full Bar Mexican, Latin, Spanish, Vegetarian Friendly, Gluten Free Options Lunch, Dinner, Late Night, Drinks +1 410-266-7580
Excellent
71%
Good
20%
Satisfactory
6%
Poor
2%
Terrible
1%
Overall Ratings

4.5 based on 482 reviews

Jalapeno's

Reviewed By Heather B - Wilkes-Barre, United States

We have taken our son, daughter-in-law, and young grand-daughter here several times and always enjoyed it thoroughly. The tapas are many and varied, and always delicious. We always order several and share them. Entrees are equally delicious, and perfectly cooked. Do make reservations, as they get quite busy!

3. Dry 85

193B Main St, Annapolis, MD 21401-2006 Takeout, Outdoor Seating, Seating, Waitstaff, Television, Wheelchair Accessible, Serves Alcohol, Full Bar, Accepts American Express, Accepts Mastercard, Accepts Visa, Accepts Discover, Highchairs Available, Free Wifi American, Bar, Pub, Vegetarian Friendly Lunch, Dinner, Brunch, Late Night, Drinks SGD 52 +1 443-214-5171
Excellent
61%
Good
30%
Satisfactory
7%
Poor
1%
Terrible
1%
Overall Ratings

4.5 based on 157 reviews

Dry 85

A modern industrial take on a Prohibition- era speakeasy. A place where you would sneak a bourbon, craft beer and gourmet comfort food meal if Prohibition were still the law of the land today.

Reviewed By ExRIGuy - Virginia

Some hits and misses: they couldn’t make a bloody mary to save their life and clearly skimped on alcohol when you order say, Grey Goose versus house vodka. On the meals the brioche buns on the sliders were just stale and nasty. Fries came out luke warm and soggy.

BUT, this is still a great place with a speakeasy vibe and upscale crowd. Stick to burgers and whiskeys and nothing fancy and you will leave happy. But this is no Iron Rooster food wise.

4. Boatyard Bar & Grill

400 4th St, Annapolis, MD 21403-2504 Takeout, Seating, Waitstaff, Parking Available, Television, Highchairs Available, Wheelchair Accessible, Serves Alcohol, Full Bar American, Bar, Seafood, Vegetarian Friendly, Vegan Options, Gluten Free Options Breakfast, Lunch, Dinner, Brunch, Late Night +1 410-216-6206
Excellent
53%
Good
35%
Satisfactory
9%
Poor
2%
Terrible
1%
Overall Ratings

4.5 based on 1 reviews

Boatyard Bar & Grill

The Boatyard is where local sailors, fishermen and lovers of the Chesapeake enjoy pint drinks, great crab cakes and the freshest local seafood. Specialties include smoked fish of the day (on premise), cream of crab and Maryland crab soups and an extensive list of crab and seafood specialties. The First Lady came from the White House to enjoy our crab cakes. The Boatyard has the most extensive raw bar in the area including a variety of oysters, clams, shrimp and mussels. The Boatyard receives awards for being most family friendly and having the best burger on the Bay. Its weekend brunch is the best in the area. The Boatyard is located in the historic maritime district of Eastport-a short walk or water taxi from Annapolis City Docks. Its photo boat films the local sailing races and shows them nightly. Named by Coastal Living, Sailing World and Sail Magazine as one of world's top sailing/boating restaurants.

Reviewed By Ottrose - Annapolis, MD

That rare place where both locals and touristas hang, so what else do you need to know?! Solidly above average everything, great beers on tap, very nice oyster selection, great location (if you park in downtown Annapolis somewhere, just walk over the Eastport bridge, which is easy and recommended, take the first left and you’re two blocks away). Dick has been a supporter of all things local (such as the Maritime Museum) since Moses was a newborn. That’s not the reason to go, but it’s nice to know you’re supporting the gestalt of Annapolis/Eastport when you do!

5. Iron Rooster

12 Market Space, Annapolis, MD 21401-1816 Takeout, Reservations, Outdoor Seating, Seating, Waitstaff, Television, Highchairs Available, Serves Alcohol, Full Bar American, Vegetarian Friendly, Vegan Options, Gluten Free Options Breakfast, Lunch, Dinner, Brunch +1 410-990-1600
Excellent
64%
Good
26%
Satisfactory
7%
Poor
2%
Terrible
1%
Overall Ratings

4.5 based on 1 reviews

Iron Rooster

Reviewed By SBS20001 - Washington DC, District of Columbia

We had lunch there on a Saturday and waited about 40 mins for a table for two. I very much enjoyed my crab hash. The hash browns were very crispy, though the amount of crab in the crab hash was less than optimal. Service was good and I enjoyed the decor.

6. Sin Fronteras Cafe

2129 Forest Dr, Annapolis, MD 21401-3832 Takeout, Reservations, Seating, Waitstaff, Parking Available, Television, Highchairs Available, Wheelchair Accessible, Serves Alcohol, Full Bar Mexican, Latin, Central American, International, Spanish, Vegetarian Friendly, Gluten Free Options Lunch, Dinner SGD 13 - SGD 24 +1 410-266-0013
Excellent
62%
Good
27%
Satisfactory
9%
Poor
1%
Terrible
1%
Overall Ratings

4.5 based on 192 reviews

Sin Fronteras Cafe

Excellent local eatery offering Mexican and Latin cuisne.

Reviewed By larryAnnapolis - Annapolis

We have dined here several times and it has been excellent each and every visit. The food is very fresh and authentic. The restaurant is always crowded and lively. I really like that they combine dishes from several countries in South/Central America which adds even more diversity and interesting items to the menu!!

7. Lewnes Steakhouse

401 4th St, Annapolis, MD 21403-2503 Reservations, Private Dining, Seating, Waitstaff, Wheelchair Accessible, Serves Alcohol, Full Bar American, Steakhouse, Gluten Free Options Dinner, Late Night SGD 66 - SGD 66 +1 410-263-1617
Excellent
71%
Good
13%
Satisfactory
8%
Poor
5%
Terrible
3%
Overall Ratings

4.5 based on 377 reviews

Lewnes Steakhouse

The Lewnes family has been serving fine food at this location since 1921. We trust that your dining experience with us will be a memorable one!

Reviewed By Laura A - Annapolis, Maryland

My husband and I had dinner recently to celebrate our anniversary. We remembered eating there in the past and we're prepared to be blown away. Instead we found the food good and our waiter friendly but we waited longer then we would like to request things such as a new drink etc. Over all we've eaten in better steak houses. The wine selection and recommendations were great.

8. Osteria 177

177 Main St, Annapolis, MD 21401-2006 Reservations, Seating, Waitstaff, Serves Alcohol, Full Bar, Wheelchair Accessible Italian, Vegetarian Friendly, Gluten Free Options, Vegan Options Lunch, Dinner, Late Night SGD 41 - SGD 66 +1 410-267-7700
Excellent
65%
Good
22%
Satisfactory
7%
Poor
3%
Terrible
3%
Overall Ratings

4.5 based on 477 reviews

Osteria 177

Reviewed By 52Travel5202 - Washington DC, District of Columbia

We celebrated the new year at Osteria. The price fixed dinner was simply spectacular—carefully conceived, wonderfully cooked, graciously served. There was a special menu for the occasion, but it was a reflection of the great meals we have always had here. Probably the best restaurant in Annapolis and a terrific go-to place for special occasions.

The wait staff knows the food well. It’s impossible to go wrong taking their advice.

Highly recommended.

9. O'Leary's Seafood Restaurant

310 Third St, Eastport, Annapolis, MD 21403-2510 Takeout, Parking Available, Serves Alcohol, Reservations, Seating, Waitstaff, Free Off-Street Parking, Wheelchair Accessible, Full Bar, Wine and Beer, Accepts American Express, Accepts Mastercard, Accepts Visa, Accepts Discover, Accepts Credit Cards American, Seafood, Contemporary, Gluten Free Options, Vegetarian Friendly Dinner SGD 37 - SGD 49 +1 410-263-0884
Excellent
61%
Good
23%
Satisfactory
9%
Poor
3%
Terrible
4%
Overall Ratings

4.5 based on 345 reviews

O'Leary's Seafood Restaurant

Reviewed By Gail B - Annapolis, Maryland

We are six locals from Annapolis. We really want a great seafood house and want this restaurant to fix this problem so we can support it! O'Leary's last night was somewhat disappointing. The food was spotty in quality. My fish was cooked perfectly and presentation was very nice. My neighbor's fish was terrible and uneatable. Same fish dish! After showing this to the waitstaff it was redone but every other person was finished their dinner. The Scallop special was not served hot but tasted fine. And their signature rockfish was thought to be heavily battered and unappetizing. This restaurant is very cute and cosy. Great service, a nice wine list and parking! The impression was that the kitchen needs to do a better job if you want repeat local customers. No one in the group after spending a fair amount of money on drinks, wine and food are in a hurry to return here. It's really a shame! The restaurant for a Friday night was far less than full the whole time we were seated. Maybe they need to look into the reasons why.

10. Mason's Famous Lobster Rolls

188 Main St, Annapolis, MD 21401-2008 Free Wifi, Takeout, Seating, Wheelchair Accessible, Highchairs Available American, Seafood, Fast Food Lunch, Dinner +1 410-280-2254
Excellent
55%
Good
34%
Satisfactory
8%
Poor
2%
Terrible
1%
Overall Ratings

4.5 based on 235 reviews

Mason's Famous Lobster Rolls

Mason's serves Fresh Maine Lobster, Crab, and Shrimp Rolls, Chowders, Bisques, and Maine Root soda's all direct from Maine!

Reviewed By George H - Jericho, New York

This small unpretentious place is a true find for a delicious moderately priced lobster lunch.
Various styles of lobster roll and lobster salad are offered...prices around $14 per. Good quantity of fresh--not frozen--lobster meat assures you of a quality lobster roll. You'll probably want a second one, so consider getting the jumbo or an assortment of three if you're really into lobster!

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