FREE Happy Hour + Live Jazz at Underground Speakeasy

Do you like live music, draft beer, and not spending money? If you answered yes to at least two of these, you should probably keep reading.

Every Monday evening, The Speakeasy Sessions take place on the lower level of The Gin Mill, a longtime Upper West Side favorite located at 442 Amsterdam Avenue (between 81st and 82nd streets).

It starts with a free happy hour (well drinks and draft beers) from 8 p.m. to 9 p.m. Then, a live, cover-free concert takes place from 9 p.m. to 11 p.m.

People smiling because they’re having free drinks and listening to free live music at the Speakeasy Sessions

This coming Monday, September 23, fans of live jazz (or just people who want free drinks) can congregate to enjoy the musical stylings of Emmy-nominated trumpeter and singer Benny Benack III, a Pittsburgh native representing the third generation of his family’s jazz legacy. Benack will be performing alongside Joe Saylor (a drummer on “The Late Show with Stephen Colbert”) and Philip Kuehn (a legendary bassist who’s performed with many of the greats, and even at the White House).

Benack has performed with artists including Josh Groban, Diplo and Isaac Mizrahi, and at prestigious venues like Jazz @ Lincoln Center, Birdland and Smalls Jazz Club, where he has a weekly residency. He’s also been on television shows including NBC’s “Maya & Marty” and “The Late Show with Stephen Colbert,” and has been a special guest with the Pittsburgh Symphony Pops Orchestra, the Columbus Jazz Orchestra and the Minsk Philharmonic Orchestra.

The Speakeasy Room is rustic and charming with features like a vaulted brick ceiling, crystal chandeliers, a mahogany bar and working fireplace. Concerts cover genres spanning from rock to folk to jazz and beyond.

So, if you want to start looking forward to your Mondays, head on over to the Speakeasy Sessions and uncover the Upper West Side’s best kept secret.

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