A Food Lover's Guide to Annapolis, Maryland

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Advisor - Kate Kempler
Curated By

Kate Kempler

  • Annapolis

  • Arts & Culture

  • City Travel

  • Food & Wine

  • Local Culture

  • Local Food

  • Sightseeing

A historic building with a dome and spire is seen at the end of a tree-lined street under a clear sky.
Curator’s statement

Situated on several large tributaries of the Chesapeake Bay, Annapolis is the capital of Maryland. It’s a quaint, historic city with lots of heart and personality. It’s perfect for a long weekend with the family, a girls trip for some good food and spa time or just a nice place to visit for a day if you’re staying in Baltimore or Washington, DC.

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Where to stay in Annapolis

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Things to do in Annapolis

City street buildings and store fronts at nighttime

Visit Naval Academy Grounds: Annapolis is home to United States Naval Academy. Situated right downtown, you can tour the grounds and catch a game at the Navy Stadium if you're visiting in the fall.

Annapolis Maritime Museum and Park: Located in the Eastport neighborhood, this charming museum and venue gives you a glimpse into the history of maritime activities in Annapolis. It also offers sailing tours and boat cruises, weather permitting. Take some time to enjoy the lovely adjacent park as well.

Sandy Point State Park: Sandy Point is a great way to put your toes in the sand without having to go all the way to the ocean. You also get a lovely view of the Chesapeake Bay Bridge from some of the beaches. If you're visiting around the holidays, there's a drive-through light display that's delightful for families.

Tour the State House: Annapolis is the capital of Maryland, and, as such, is the center of government. If politics and history are your thing, take a tour of the Maryland State House.

Banneker-Douglass-Tubman Museum Speaking of history, the Banneker-Douglass-Tubman Museum is located right behind the Courthouse off of Church Circle. Stop in for excellent exhibits promoting and interpreting African American heritage in Maryland.

Mural walking tour: A cool, relatively new addition to downtown Annapolis is a walking tour of all the murals that have popped up over the last few years. My personal favorite is the Ruth Bader Ginsburg and Thurgood Marshall mural.

Check out a concert at Rams Head: Rams Head Brewery is the oldest active brewery in Maryland, and they also happen to have an intimate concert venue right on West Street. Check out their website for upcoming performances and take in some live music or comedy while you're in town.

Peruse the shops on Main Street.

Whether you're in the market for local artisan goods, tea and spices, tote bags made out of sails or vintage books, there's something for everyone.

Places to eat & drink in Annapolis

Three hands holding different styles of coffee cups from a top-down view.

Rise Up Coffee Roasters: The coffee is delicious, small businesses are the best and the breakfast sammies are life-affirming.

Vida Taco Bar: A laid-back option for delicious tacos and my personal favorite nachos. They also feature a margarita/sangria beverage called purple drank that's a must-try.

The Choptank: Upscale waterfront dining with great views of the City Dock area and the Naval Academy skyline. Enjoy offerings from their raw bar as well as Maryland blue crab dishes.

Luna Blu: A tiny Italian spot that has some of the best pastas and pizzas I've ever had. Check out their website to see if one of their special wine pairing nights is happening during your visit.

Davis’ Pub: Davis' Pub is where the locals eat. Tucked away on a quiet, residential street in Eastport, you can get a local beer on draft and enjoy some of the best crab cakes around.

Reynolds Tavern: If you've ever been to Colonial Williamsburg and enjoyed the historic tavern dining options, Reynolds is for you. They offer afternoon tea service as well as lunch and dinner. If the weather is nice, sit out on their back patio, but if it's not nice, ask to sit downstairs in their pub by the roaring fire.

Vin 909 Wine Cafe: Consistently noted as one of the best restaurants in the area, Vin 909 offers farm-to-table fare and an incredible wine selection.

Always Ice Cream: Perfect place for a sweet treat to end your day. They make their own ice cream with flavors ranging from Fruity Pebbles to Zebra Cake to Chocolate Chocolate Brownie Batter. Always Ice Cream is also available on Main Street at the Annapolis Ice Cream Company.

Galway Bay: If you're looking for the closest thing to a Dublin pub as you can find, here's your place. Galway Bay has awesome, traditional Irish food offerings and sells its famous house-made eggnog during the holidays

Libbey’s Coastal Kitchen and Cocktails: Just across the Chesapeake Bay Bridge, about 20 minutes outside of Annapolis, stunning sunset views of the Bay and delicious seafood.

Chick and Ruths: Staple of Annapolis; enjoy a crab cake or try one of their Colossal Challenges (think a six-pound milkshake and 1.5-pound sandwich) as featured on Man v. Food.

Where to drink:

Dry 85: Featuring rotating seasonal cocktails and all the whiskey options you could dream of, Dry 85 is an excellent choice for a beverage.

Red Red Wine Bar: Featuring wine flights, wines on tap and traditional bottles, this wine bar is a wine lovers dream. They often have live music, and truly go all out with the holiday decor if you're visiting in the winter.

Level: Only open from 5 pm on, Level offers a really excellent array of craft cocktail options.

Great place to Stop by Forward Brewing for a happy hour brew. Another Eastport establishment, Forward Brewing has a tasting room and outdoor patio that are perfect for a relaxing afternoon.

Advisor - Kate Kempler

Travel Advisor

Kate Kempler

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This guide is a part of our ongoing series on travel to Annapolis. For more travel tips, check out Fora Advisor Jill Albino's guide, Pet-Friendly Things to Do in Annapolis, Maryland.