Federal House Bar and Grille sits on Market Space in Annapolis
The Federal House Bar and Grille was founded in 1830. Image courtesy of Federal House.

Whether past or in the making, Annapolis is a showcase of history. From its prominent placement along the Eastern Barbary Coast of North America to its rich colonial history and beautiful curation of colorful homes and cobblestone streets. Annapolis is abundant with historical landmarks and no shortage of historic restaurants and pubs.

This year, holiday pub crawl goers will have to get a bit creative and grab their favorite cocktails and drafts to go, due to limited indoor capacity at Anne Arundel County bars and restaurants. To continue serving good food, beverages, and holiday cheer, many restaurants and pubs have switched to outdoor dining, carry-out only, and curb-side pick up. Regardless, here are a handful of historic Annapolis pubs you must add to your holiday pub crawl itinerary.

Galway Bay Irish Restaurant


Galway Bay on Maryland Avenue
Formerly the home of historic ‘The Little Campus Inn’, the building now houses the popular Irish Pub, Galway Bay. Image courtesy of Galway Bay.

Some places thrive on heritage, tradition, and good friends. Galway Bay is one of those places. Part of their heritage and holiday tradition includes friends and family gathering around their tables enjoying tall glasses of the famous Galway Bay Eggnog. The buildings that house the popular Irish Pub were built between 1897-1903.

63 Maryland Ave.

Annapolis, MD 21401

(410) 263-8333

Galway Bay Irish Eggnog Gift Basket
Galway Bay is well known for it’s authentic imported Irish Eggnog. Image courtesy of Galway Bay.

Drummer’s Lot 

Tucked away, practically hidden in the historic Maryland Inn, is the Drummer’s Lot. Beyond its threshold is an old-time, charming cocktail of family and elegance. Keep your holiday pub crawl classic with a Bourbon Old Fashioned made with lots of holiday cheer and fresh fruit. Open since 1784, you can enjoy your cocktail much the same way Kings and Heads of State may have done in colonial times!

16 Church Cir

Annapolis, MD 21401

Interior pub shot of Drummer's Lot Pub
The Drummer’s Lot is one of the oldest and most historic pubs in town! Image courtesy of Historic Inns of Annapolis.

Rams Head Tavern

Are you looking for the holiday spirit of fun? Once known as the Crown and Dial Tavern in the 18th century, Rams Head Tavern should be a top landmark on your pub crawl route. Whether it is the brand new Doppelbock Lager or a not so Plain Jane Bloody Mary, Rams Head Roadhouse has a taste for you and your buds.

33 West Street

Annapolis, MD 21401

Phone: 410-268-4545

Rams Head Tavern on West Street
Rams Head Tavern sits on West Street and carries a wide variety of beer, ale and lager! Image courtesy of Visit Annapolis.

The Federal House Bar and Grille

In the mood for a pint-size holiday party with your pub crawl? Your night should end at The Fed House, which was founded in 1830. With live music every night, The Federal House Bar and Grille is sure to bring some spirit back into your holiday. You can warm your body at their outdoor fire tables and your spirit with a delicious holiday cocktail. Or, lift it with a FedHead favorite like the Champagne Super-Nova.

22 Market Space

Annapolis, MD 21401

Interior view of Federal House Bar and Grille
Interior of Federal House Bar and Grille, an historic pub on Market Space. Image courtesy of Federal House.

Historic 1747 Pub

As the name suggests, this tavern has been around the block. The pub was the original kitchen and ‘Hat Shop’ of William Reynolds according to their website. And the large brick fireplace beckons you to sit and stay awhile. Maybe you want to enjoy the holiday season in the spirit of the United States forefathers. You must make a stop along your pub crawl at 1747 Pub and take home a glass of George Washington’s Eggnog.

7 Church Cir

Annapolis, MD 21401

1747 Pub sits below Reynolds Tavern on Church Circle.
The historic 1747 Pub has been serving up food and spirits for hundreds of years! Image courtesy of Visit Annapolis.

Regardless of what stops you make along your holiday pub crawl, have fun, eat well, drink merrily, and cherish the comfort of friends and family.


Egypt English

O'Dellshae TruVarsha Wiles Robinson El Bey, artistically known as Egypt English, is a poet and spoken word recording artist. She is the force behind the poetry EP and book "Opening Ceremony Vol. 1: The Birth of Egypt English". She graduated from Frostburg State University with a degree in English Literature and an enhanced love for the art of storytelling. In addition to her poetry career, Egypt is a teacher for Art with a Heart in Baltimore, an image consultant and certified confidence coach for budding creative entrepreneurs, and the host of her lifestyle podcast, "The Monday Train". When she is not refining her crafts, you can find her making vibrant memories with her husband and son. She loves listening to a wide array of music, making energy healing jewelry, taking impromptu trips to the beach, and spending time in nature with her family. Growing up in the quiet sticks of Saponi country at Ringgold, Virginia, Egypt is captivated by the culture, hues, and hustle and bustle of Baltimore and the beautiful waters of Annapolis. Want to know more? Visit her blog egyptenglish.com, and follow her on Instagram @_leideEnglish.