Chatterbox Pleasantville

05/18/2026

THURSDAY NIGHTS AT CHATTERBOX JUST GOT A MAJOR UPGRADE 🔥🎶

We’ve been doing karaoke for years, and while we love it, we heard you — Thursday nights deserve MORE. 💥

So here’s what’s happening this summer: We’re ALTERNATING THURSDAYS to give you TWO completely different vibes. 🙌

🎤 **KARAOKE THURSDAYS** — Your favorite sing-your-heart-out night is STILL HERE. Kicks off May 21 with bringing the music. Same energy, same fun.

🍸 **HANGOUT THURSDAYS** — THIS is the new addition. Launches May 28 with on the decks. Chill, laid-back vibes that can turn UP depending on the mood and the crowd. Whether you’re coming for dinner, drinks, or just to vibe — this is YOUR night. Music curated. Energy dialed in. No two Thursdays are the same.

🌟 **PLUS: LADIES, 2-FOR-1 CRAFT COCKTAILS 9-11PM BOTH NIGHTS.** 🍹

Chatterbox has always been the spot, and now Thursday nights are about to prove it. Whether you’re singing, sipping, or dancing — we’ve got you covered all summer long. ☀️

Mark your calendars. Tell your crew. This is the summer Thursday nights in Pleasantville level up. Let’s GO. 🔥

📍 Chatterbox | 75 Cooley St, Pleasantville, NY 10570
📞 914-495-3900

02/16/2026

Chatterbox Pleasantville Presents our 2nd BIEBER FEVER BLACKOUT BRUNCH!🎉 Sunday March 1st at 12pm join us for brunch and beats by our in house DJ spinning nostalgic hits by Justin Bieber. Including a special food & drink menu - you don’t want to miss this 😊 Please call for reservations - 914 495 3900. Seats are limited.

02/16/2026

Chatterbox Pleasantville Presents our 2nd BIEBER FEVER BLACKOUT BRUNCH!🎉 Sunday March 1st at 12pm join us for brunch and beats by our in house DJ @—— spinning nostalgic hits by Justin Bieber. Including a special food & drink menu - you don’t want to miss this 😊 Please call for reservations - 914 495 3900. Seats are limited.

01/09/2026

Join us for a Galentines Day Brunch at Chatterbox on Sunday, February 8th! Celebrate the loves of your life with us - DJ starts at noon. Don’t forget to reserve your spot at Chatterboxpleasantville.com 🌷💕🎶🕛

01/09/2026

Join us for a Galentines Day Brunch at Chatterbox on Sunday, February 8th! Celebrate the loves of your life with us - DJ starts at noon. Don't forget to reserve your spot at Chatterboxpleasantville.com 🌷💕🎶🕛

12/30/2025

The DJ begins at 10 PM! Come celebrate New Year’s Eve with us, Make your dinner reservations now filling up quick. Reservations are highly recommended and can be made at chatterboxpleasantville.com

11/16/2025

11/12/2025

Wednesday November 26 with DJ & DJ of

Chatterbox Presents: Thanksgiving Eve
See you at 10:30PM ✨

10/22/2025

Save the Date 🎶🪩✨ Chatterbox Halloween Party Saturday November 1 at 10:30PM

Costumes Encouraged

Chatterboxpleasantville.com for reservations

Westchester’s Premier location for Great Food, Great Cocktails, and amazing Nightlife

Join Us on the Dancefloor with beats from DJ and cocktails from and

10/20/2025

Mondays are Fundays too, if you know where to go 😉

Footballs Specials & Wings starting at 5PM Tonight at the Bar & 6 Flat Screens for Texans Seahawks, Come Hang

📍Chatterbox Restaurant & Bar: 75 Cooley Street Pleasantville, New York 10570