The first time I had a Dartmouth Highball was during a stage at Island Creek Oyster Bar back in 2011. It was one of the first drinks I was instructed to make, and if my memory serves me right it was on their drink menu at the time. It’s an Eastern Standard original, developed by Bob McCoy – who also happened to be overseeing my stage that night.
Created years prior for a Pimm’s Cup section on ES’s menu, Bob was inspired by the refreshing and herbaceous aspects of a classic Pimm’s Cup, but was also looking create a boozy, tea-like concoction that was lighter and more easy-drinking than the traditional Long Island one. The two ideas came together and the Dartmouth Highball was born. The cocktail was named after the Dartmouth, one of the three British East India Company ships looted by the Boston Tea Party.