Knock twice, whisper the password, and enter the clandestine world of a speakeasy. These dimly lit, unidentifiable bars were the only way Americans could enjoy a drink during Prohibition in the 1920s and early 1930s. Alcohol is long legal now, but these criminally delightful establishments are making Westchester County a speakeasy destination.
Operation Midnight Climax
White Plains
Sweet Temptations’ coffee and dessert bar has an extra-sweet surprise: The vending machine is actually a door that transports guests back in time at the county’s newest speakeasy. Drenched in lush pink light and outfitted with velvet booths, Operation Midnight Climax (OMC) is every maximalist’s dream destination. Playful cocktails, such as the Vice City (gin, strawberry, rum, Cocchi Rosa, Co2, pina colada, and cocoa amuse-bouche), complement a menu of classic cocktails and elevated small plates, including Bang Bang shrimp. Leave no (electronic) trace behind — OMC is cash only.
View this post on Instagram
Pour
Mount Kisco
Right off Main Street in Mount Kisco sits an unassuming yellow house with blinds drawn. Walk through the door and the mystery dissipates as you step into a wonderfully unique speakeasy bar. Pour maintains the original floor plan of the house, and guests can explore the various candle-lit rooms decorated with pictures from years past. The only thing better than the ambiance is the menu, featuring an array of wines from around the world. In addition, sample a sinfully sublime CBD-infused cocktail, perfect with one of the flatbreads.
Prohibition’s End
New Rochelle
In the basement of what appears to be a residence, you’ll find this craft cocktail Prohibition-themed bar that’s rumored to have been a bar back in Prohibition times. Sip on The 1933, a mix of rye, vermouth, and black walnut bitters, aptly named for the year Prohibition ended. While speakeasies back then focused on keeping quiet, Prohibition’s End turns up the volume with karaoke and DJ nights.
Sinaloa Lounge
Elmsford
Most mirrors offer just a reflection, but at Elmsford’s Invito Restaurant, the mirror serves as a portal to a behind-the-scenes party on Thursday through Saturday nights. Sip on craft cocktails, like the refreshing El De Oaxaca with mezcal, chocolate and orange bitters, and demerara sugar. On Fridays and Saturdays, get down to the DJ beats until 2 a.m. and enjoy a Mexican-inspired menu of small plates. Flautas, filled with potatoes, peppers, and cheese, are an excellent choice, or split the crispy calamari dusted with flour and served with lemon-jalapeno sauce and lemon zest.
The Speakeasy at Divino
Hastings-on-Hudson
Through the alleyway, down the stairs, and under the bridge: It’s where Italian cuisine meets the speakeasy scene. Enjoy fare from Divino Cucina Italiana, situated upstairs, and pair it with a signature speakeasy cocktail like the Cocoa Old Fashioned: a mix of whiskey, simple syrup, and orange and cocoa bitters. Visitors are immersed in an authentic Prohibition-era vibe, surrounded by mysterious mason jars that sit along wooden cabinets throughout the space. Fall further into the 1920s on Thursday nights with live jazz.
Whistling Rail
Bronxville
Hidden at one end of Bronxville’s historic former train depot is a first-class ride to swanky cocktails and sexy small plates. As trains rumble by, enjoy seasonal cocktails, cheese and charcuterie boards, and fresh hummus in this artfully adorned cozy lair. The hottest ticket in town is the Last Train to Guadalajara, a Mexican-inspired tequila and mezcal cocktail sure to warrant a round-trip back for more.
Erin Maher is a writer and Westchester native. When not writing, Erin can be found on the pickleball courts or scrolling through pictures of dogs on Instagram.
Related: 4 Gin-Based Cocktails That Are Supremely Sippable in Weschester
