Boston Historic Tavern Tour
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Boston Historic TAVERN Tour

Travel through time visiting classic off-the-beaten-path drinking establishments and sample cocktails that only a local would know exist!

1800’s: Visit the home of Boston’s oldest cocktail, the Ward Eight at a Top 20 legendary U.S. restaurant, dating back to 1883.

1920’s: Enjoy historically inspired local cocktails like the “Molasses Flood 1919” over vintage machine cut ice, in an establishment that hasn’t changed since the 1920’s.

1930’s: Sample locally brewed Cask Ales from the largest selection on tap in the U.S., served in an old corset store.

1950’s: Try a Boston Cream Pie where it first originated and the location of JFK’s bachelor party in 1953.

1960’s: You’ve heard of comfort food, now sample ‘comfort cocktails’ invented by local mixologists in Boston’s most retro speakeasy basement bar.


Along the way, your expert guide and author will share his local tavern knowledge: 

  • Learn about authentic drinks including Flap Dragon, Flip, Grog, Gumption, Jingle, Syllabub and Whistle Belly Vengeance.
  • Hear how taverns played a role in the Boston Tea Party, Paul Revere’s Ride, the Siege of Boston and the Battle of Bunker Hill.
  • Hear stories of tavern keepers of bygone Boston and their colorful clientele including James Otis, Sam Adams and Judge Sewall.
  • Discover the origins of local tavern names such as the Bunch of Grapes, Bell in Hand and Green Dragon.

Start:  Downtown Crossing T Station - Finish: State St T Station (approximately 2 hours)