The Warren Tavern has been in its current location in Charlestown, on Pleasant Street (near the Bunker Hill Monument) since 1780, making it the oldest tavern in Massachusetts. When it was built, it supposedly replaced a nearby tavern burned down by the British troops either during the Battle of Bunker Hill or another Revolutionary War skirmish. Back in the day, this watering hole hosted prominent American patrons like Paul Revere, Benjamin Franklin and George Washington, making this the ideal bar to check out for a cold beer, cuppa chowder and a history lesson.
The title of the oldest bar in Boston is something of an ongoing debate, as one of the country’s first settlements, the city has more than a few historic taverns. Many of these were regular meeting spots for Colonial rebel rousers as they helped organize The Revolution—and many of them still stand today, in defiance to the rapid development surrounding them. There’s also a crop of newer old bars, opened in the past 100 years, that define some of the great neighborhoods around the city.
All have their own stories to tell, and some of these hangouts also rank among the best Irish pubs and best dive bars in Boston. If you’re looking for something a little fancier and more modern, check out our list of the best cocktail bars in Boston.
RECOMMENDED: See the full list of the best bars in Boston