The Speakeasy at The Gin Mill
Below The Gin Mill restaurant on Amsterdam Avenue on the Upper West Side, there's a room that was built to feel like a Prohibition-era private club. Vaulted brick ceilings, crystal chandeliers, hardwood floors, a mahogany bar, and a working fireplace. It's a proper room and it was designed with intention.
On Monday evenings it opens to the public as Speakeasy Sessions. Happy hour runs from eight to nine with well drinks and draft beer, and then live music takes over from nine to eleven with no cover charge. The performers who come through are actual musicians.
The rest of the week the space is available for private events: birthday parties, corporate gatherings, anything that benefits from a room that looks like it was genuinely designed around the idea of a 1920s underground bar. It's one of the better event venues on the Upper West Side precisely because it doesn't look like a modern event venue.