6 Speakeasies Serving up Serious Vibes in Westchester County

Sip and nosh in secret (sort of) at these alluring hideaways around the county.

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 the 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 Midnight Climax (a mix of vodka, lychee, Bacardi Razz, and coconut), complement a menu of classic cocktails and elevated small plates, including Moroccan lamb skewers. Leave no (electronic) trace behind — OMC is cash only.

- Advertisement -


Mount Kisco

Right off Main Street in Mount Kisco sits a yellow unassuming 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 ambience is the menu, featuring an array of rare whiskeys, like the Rittenhouse 21-year and Pappy Van Winkle. In addition, sample a sinfully sublime CBD-infused cocktail, perfect with hot pretzel bites and truffle Parmesan fries.

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 rumoured 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 on Wednesdays at its well-attended karaoke nights.

Sinaloa Lounge


- Partner Content -

Most mirrors offer just a reflection, but at Elmsford’s Invito Restaurant, it’s a portal to a behind-the-scenes party, Thursday through Saturday nights. Sip on craft cocktails, like the refreshing El Fresa with tequila, rhubarb, strawberry, lemon, agave, and clarified milk. 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 shrimp basket, featuring a fried tortilla basket with guacamole, pico de gallo, and roasted garlic sauce.

The Speakeasy at Divino


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 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.

Step downstairs and back in time at Divino Cucina Italiana’s speakeasy
Step downstairs and back in time at Divino Cucina Italiana’s speakeasy. Photo by Ken Gabrielsen.

Whistling Rail


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.

- Advertisement -
Whistling Rail offers a first-class ticket to craft cocktails and jazzy vibes.
Whistling Rail offers a first-class ticket to craft cocktails and jazzy vibes. Courtesy of Whistling Rail.

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

Our Healthcare Heroes Awards event takes place on May 9!

Our Westchester Home Builders Awards take place on April 4!

Our Diversity, Equity & Inclusion Forum is March 14!

Unveiled: A Boutique Bridal Brunch is February 25!

Our Best of Westchester Elimination Ballot is open through March 6!

Holiday flash sale ... subscribe and save 50%

Limited time offer. New subscribers only.