Uncle Cheef Is a Must-Visit Live Music Lounge in Brewster

In Putnam County, Uncle Cheef is a new hotspot for tapas and live music curated by Grammy Award-winning saxophonist Ian Hendrickson-Smith.

The Hudson Valley’s newest home for live music recently opened in the Village of Brewster. Uncle Cheef, named after owner, Tonight Show musician, and five-time Grammy Award-winning saxophonist Ian Hendrickson-Smith, is a jazzy venue for good tunes, American tapas-style small plates, and boozy beverages. The warm and inviting space presents the very best of live music, curated by Hendrickson-Smith himself, every Wednesday through Sunday.

Although he only opened his music lounge earlier this year, Hendrickson-Smith has been successfully working in the music industry for about three decades. Starting his jazz career right out of college in the late 1990s, he has since played professionally with big names like Amy Winehouse, Lady Gaga, Bob Dylan, and Queen Latifah. Now, he is on the road with The Roots and is featured on The Tonight Show Starring Jimmy Fallon every week.


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For Hendrickson-Smith, the opportunity to open his own music venue has been a dream for 30 years. In fact, 12 years ago, he was very close to setting up shop at a location in Brooklyn, but life had other plans. Fortunately, his dream was finally realized after he and his wife and business partner Jenny moved to Brewster and noticed there was no accessible adult hangout spot with a great vibe. In an effort to fill this niche and create something fun and unique, Uncle Cheef was born to bring the community every aspect of the experience, from great service to live music.

Not only is the music lounge perfectly nestled between popular Hudson Valley locales like North Salem and Pawling, but also “the second-story location gives the place a very transformative private feeling when you’re in the space. [It’s] like you could be a million miles away from all your troubles and just enjoy soaking up all the world-class live music with a next-level cocktail in hand while chowing down on lovingly made small plates with your friends,” says Hendrickson-Smith.


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At Uncle Cheef, visitors can expect live performers ranging in music genres from jazz and blues to singer-songwriters and funk. Even though Hendrickson-Smith has an ear for jazz, being that he plays saxophone for a living, he books plenty of artists outside of the genre to give his audiences a great show that they’ve never seen before. Stay updated on Uncle Cheef’s calendar, which Hendrickson-Smith populates with extensive biographies and videos on his booked artists for visitors to browse before a performance.

Newcomers who are looking to get the full Uncle Cheef experience should be sure to try the Southern-style red beans and rice – a family recipe recommended by Hendrickson-Smith that has been approved by the few New Orleans natives that have played the club. Go for the short-rib sliders for a barbecue fix or a cheese and charcuterie board with a bottle of wine to elevate your visit. As far as cocktails go, the Uncle Cheef Old Fashioned and classic Negroni take the cake.


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Even though Hendrickson-Smith has a packed work schedule as he navigates his three different gigs, he strongly believes that if you love what you do for work, you’ll never work a day in your life, and he says he is living proof of that sentiment. With Uncle Cheef, he and his wife are happy to see the community come together in fellowship through art and booze. They both hope to create a cultural oasis that can last for decades in the lower Hudson Valley region.

“We want people to walk away from their experience refreshed, inspired, and enriched. It’s our favorite thing in the world to see smiling faces and hear the ‘We’ll be back!’ comments as people are making their way home,” he enthuses.

Uncle Cheef is located at 988 Route 22 in Brewster.

Related: 6 Hudson Valley Artists and Musicians to Listen to Now

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