5. Tooker Alley
Neighborhood: Prospect Heights, Brooklyn
Address: 793 Washington Ave.
Washington Avenue in the Prospect/Crown Heights neighborhood gained some real boozing credibility when Tooker Alley opened this past October. Helmed by Pegu Club alum Del Pedro, this parlor is thick with nostalgia for the Chicago drinking dens of the early 20th century, in particular the storied Dil Pickle Club. The period scene is fixed with filament lighting, iron crank stools and tables, and a re-purposed oak bar made from a flatbed truck.
Contributing to the transporting vibe, the cocktail menu is a kind of storybook, with odes to gin, a history of the martini, and explanations about the classic cocktails. The Thelonious Monk, one of Pedro's creations, is a take on the classic Amber Dream. Fittingly, it's made with monk-crafted Benedictine and named after the famous jazz musician whose music often fills the space.