. The top 5 restaurants in Annapolis (why it's not about the food) : Budget Travel Adventures

The top 5 restaurants in Annapolis (why it’s not about the food)

Crab cake sandwiches.  Black pudding.  Flash fried spinach.  Scrambled eggs.  Homemade ice cream.  These are just a sample of the foods I ate at various restaurants in Annapolis.

However, delicious food is not what I had planned for my visit to Annapolis on my College Football Travel Tour.

On my first night, I enjoyed an intimate concert with the lead singer of the band Tonic, Emerson Hart at The Ram’s Head.  The next morning, I ate at a crowded diner, said the Pledge of Allegiance, and rubbed shoulders with former governors of Maryland.

That weekend, I met future leaders and soldiers at the United States Naval Academy, attended the Army Navy football game, and got photos of President Obama.

Annapolis welcomed me home and made me feel like a local.  There was something different about this place.  My visit to Annapolis even has me writing about food.

Food isn’t a big part of my travels.  Honestly, this list of the 5 best places to eat in Annapolis has as much to do with the people I met as it does the food itself.

I was impressed by the quality and variety of food in Annapolis.  It’s really good.  For a traveler who doesn’t write a lot about food, it was good enough to expand my waistline.

5 of the best restaurants in Annapolis

From food stories to success stories, every morsel at these places tells a story.  I enjoyed the food in Annapolis.  I loved the experience even more.

Chick and Ruth’s Delly

Chick & Ruths Delly Annapolis best restaurants in Annapolis

From the outside, this looks like a cozy, busy diner where locals can grab a bite to eat.  It’s so much more than that.

On my first morning in Annapolis, Susan Steckman of the Annapolis Visitor’s Board brought me to Chick & Ruth’s so I could experience it.  On a busy Thursday morning, long time manager Chuck Munyon took some time to sit down and talk with us.  I ordered an omelet and toast with a side of grits as I listened to his stories.

Ted Levitt took over Chick & Ruth’s many years ago after his parents – Chick & Ruth – passed away.  Ted is a kind soul who serves good food in an incredible atmosphere.  He used to perform magic tricks for kids.  He’s sponsored a number of kids at the Naval Academy.  And he’s put Chick & Ruth’s on the map.

Chick & Ruth's Delly Pledge of Allegiance best restaurants in Annapolis

The Pledge of Allegiance

Years ago, Ted’s son told his dad that they could no longer say the pledge of allegiance at school.  Ted started saying the Pledge of Allegiance at Chick & Ruth’s.  Now every weekday morning at 8:30 and every Saturday and Sunday at 9:30, customers and employees stand, face the flag, and cite the Pledge of Allegiance.

In a city that is home to the US Naval Academy, it feels like the perfect thing to do.

These days, Chick & Ruth’s is known to the outside world for their colossal shake and burger.  Featured on Man vs Food, Chick & Ruth’s offers a colossal challenge – drink a 6 lb shake and a 1 to 1 ½ pound burger.  Finish it and you get a t-shirt and your name on the website.

Most don’t.   A few customers each week share the contents right on the floor of the diner.  Only at Chick & Ruth’s.

Chick & Ruth’s Delly is located right in the middle of downtown on 165 Main St and offers a variety of affordable menu items in a diner atmosphere for breakfast, lunch, and dinner.

Piccolo Roma

Piccola Roma best restaurants in Annapolis

This Italian restaurant in downtown Annapolis has gone through its own renaissance thanks to owner Marc Lucas.  When it originally closed in January 2009, the talented chefs left and went to Texas.  When it opened again in August 2009, Marc brought them back.

Piccola Roma Annapolis food Italian pizza flash fried spinach best restaurants in Annapolis

Italian pizza and Flash Fried Spinach

Marc is a Naval Academy graduate who knows the area well.  He knows what it means to operate a business here.  And he enjoys what he does.  I spent hours talking to Marc when I visited Annapolis.  I learned a lot about life here, the people, the community, and his life.

So when it came time to eat the food, I had high expectations.  Being the creative perfectionist that he is, Marc met those challenges with Crab Cakes, Italian style pizzas, and his newest creation – flash fried spinach (all the benefits of eating a vegetable but tastes like a potato chip).

Don’t let the fancy food or white table cloth environment intimidate you.  You will feel right at home, enjoy a taste of Italy from some master chefs, and relax with a nice wine or Marc’s latest drink creation.

Tourists, locals, sailors, and the Governor can enjoy a delicious Italian meal at Piccolo Roma’s.  I enjoyed my visit with Marc as part of my Annapolis Food Tours.  However, good food and company made me go back more than once.

Ristorante La Piccolo Roma is located on 200 Main Street which serves a mix of Italian food and local Annapolis style food ranging in price from $10 – $30.

Galway Bay

Galway Bay Irish food best restaurants in Annapolis

Who would have imagined that you could find authentic Irish food just a few blocks from the US Naval Academy?

At Galway Bay, traditional Irish Food and drink is what’s on the menu.  Green is more than just the color of Ireland as the restaurant takes an environment-friendly to dining .  With dishes like Corned  Beef and Cabbage, Shepherd’s Pie, and the Irish Mixed Grill,  Galway Bay seeks to bring a piece of Ireland to Annapolis.

Galway Bay Irish food Annapolis Irish Mixed Grill best restaurants in Annapolis

bangers, black pudding, chips, and Irish food

For me, the restaurant had a cozy pub feel.  While I enjoyed the Irish Mixed Grill, I started chatting with a local named Donna – a former employee of Galway Bay.  She had the Irish gift of gab as she shared her life, story, and experiences with me over dinner.  She even picked up the tab to pay for my meal when we were done.

I wish I had spent more time at Galway Bay and gotten the chance to chat more with the owners, like GM Finton Galway.  If first impressions mean anything, Galway Bay’s success is attributed to more than just the luck of the Irish.

Galway Bay is located at 63 Maryland Ave and serves authentic Irish cuisine and drinks ranging from $9 to $21 for appetizers and dinner.

The Boatyard Bar and Grill

The Boatyard Bar and Grill best restaurants in Annapolis food

Ever wanted to set sail on an expensive yacht?  Well now you can eat at a restaurant with a maritime feel and lots of seafood overlooking a few.

Manager Kenneth Nankervis shared the story of this place with me.  Dick Franyo is a man who understands the sailing community.  As an avid sailor, he wanted to create a restaurant that made you feel at home right off the boat.  The Boatyard Bar and Grill has won the award as best sailing bar by an international sailing magazine.

Dick is incredibly active in the community with fishing tournaments and charities.  Located just across the river, The Boatyard Bar and Grill is part of Annapolis but is actually located across the bridge in Eastport.

The Boatyard Bar and Grill Annapolis Fod Crab cake sandwich best restaurants in Annapolis

Crab cake sandwich

While the postal code is still Annapolis, Eastport has a vibe and feel that is far different.  This is the home of sailors.  And this is where they come to meet and hang out.

However, this place is also for families as it offers something for everyone – pizzas, sandwiches, chicken, surf and turf, and more.  As I enjoyed my meal of oysters and Crab Cake Sandwich, the place was full of families and locals on a Sunday afternoon.

Four kitchens, an expanded dining area, and a variety of good food bring lots of people here every week – from locals to sailors far away from home.  After a meal like this, I grabbed my yacht and sailed the Chesapeake Bay.

OK, I didn’t but I really wanted to.

The Boatyard Bar and Grill is located at 400 4th Street Annapolis (but in the town of Eastport).  They serve a limited breakfast and full menu 7 days a week and are open most nights until 11 pm.  Prices range from $6 to $36.

Annapolis Ice Cream Company

Annapolis Ice Cream Company best restaurants in Annapolis

Who wants ice cream for dinner?  I’m just kidding kids – don’t eat ice cream for dinner.  But a little for dessert is OK – especially if you are in Annapolis.

Walter and Nancy Giera may be the hardest working people in Annapolis.  Back in the 90s, they moved here from New Jersey and fell in love with the city.  On a search for ice cream, they couldn’t find anything homemade.  So a few years later, they decided to make their own.

Nancy and Walter use their own homemade recipes to make over 100 flavors of ice cream – every single scoop made right at home.  36 flavors are always available along with milkshakes, pies, and sundaes.  They use fresh ingredients and every bite tastes fresh and delicious.

Annapolis Ice Cream Company spoons best restaurants in Annapolis

Create your own spoon for the wall!

They are open 7 days a week, every day of the year except one – Christmas Day.  After work is done, they head home each night to make more ice cream.

This place is popular with the locals and tourists – but not just for the ice cream.

A tradition was started many years ago by a former employee who decorated her spoon.  Now, markers are available for every customer to create their own design.  Currently, 12,000 spoons are on display.  And after my visit, one more was added.

The ice cream is delicious and Nancy, Walter, and the penguin welcome you to try some and decorate your spoon for posterity.

Annapolis Ice Cream Company is located at 196 Main Street and is open 7 days a week.  Regardless of the weather, enjoy your favorite homemade flavor.

Dining in Annapolis – it’s more than just food

Annapolis surprised me with the variety of food.  And while this list includes just a few of the many places to eat, and shops, these were my favorite restaurants in Annapolis.

And the food was pretty good too.

Thanks to Visit Annapolis and Susan Steckman for their hospitality during my visit to Annapolis.  Special thanks to Marc, Chuck, Kenneth, Walter and Nancy for sharing the love of their restaurants and delicious food.

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Filed Under: College Football Travel TourFood and drinkTravel TipsUS Naval Academy


RSSComments (12)

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  1. I have heard more than once that Joss has the best sushi on the East coast. I have not been and cannot confirm–but intend to visit on my next trip to Annapolis.

  2. I haven’t been to Annapolis in a while and reading this brings back a lot of wonderful memories. This is a great list, Jeremy. Will keep it handy for my next visit

  3. Laurel says:

    I had totally forgotten about Chick & Ruth’s Delly, although it was my favorite restaurant in Annapolis and the crab cakes were amazing. One of the things I miss the most about living in Annapolis is eating crab several times a week.

    • I had more crab that weekend than I’ve had in years. The food was very good. I ate more than I normally do on these trips but it was hard not to. Annapolis was probably the city that surprised me the most in all of my travels in the US.

  4. Amanda says:

    Mmmm, now I’m hungry! Sounds like a great variety!

  5. These restaurants are really very good and withing the budget.Thanks for sharing the information.

  6. Naomi says:

    Thanks for this post – we are planning a trip to the area soon, and I appreciate the insight on Annapolis food!! You’ve got me looking forward to it.

    • That’s great Naomi! I really loved Annapolis. The city really surprised me. Food is huge in Annapolis. Check out the food tour if you want to get a sample of different dishes from a variety of place.

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