Tipsy History: The Historical Pub Crawl of Annapolis

Toast to rebels, rum-runners, and rye. This is Maryland history the rowdy way—one bold pour and untold story at a time.

Come raise a glass with us on a historical pub crawl that shares the untold stories of how drinking shaped Annapolis, Maryland, and the nation itself. At each stop, we’ll dive into a different era— paired with a recommended drink that was all the rage at the time. Join us to toast the past, enjoy the present, and experience history with a tipsy twist.

Timed with happy hour, this tour is the perfect start for anyone who loves whiskey, spirits, and tipsy history.

Please note

As this tour will visit a few pubs in downtown Annapolis please dress accordingly as we will depart rain or shine. There is limited walking on this tour so be prepared to walk on brick sidewalks and in some cases to go up stairs if some of our partner pubs are lively.

Please arrive 10-15 minutes early at our first location so we can start on time.

Although we have recommended drinks at each stop they are not included with the price of the tour. This allows our guests to enjoy alcohol at their own pace and responsibly. If you’d prefer a different drink instead of the featured one, we ask that you stick to beer, wine or non-alcoholic beverage to help keep the tour moving smoothly.