Pilars Loft

Pilars Loft Join us at Pilars Loft--Pilars Martini entertainment & inspiring upstairs space--where local artist r
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From the people that behind Pilars--where cocktails and cuisine meet concerts and community---comes Pilars Loft on Plant, where local artists rise, Winter Garden’s newest Jazz Club and Music Venue. Emerging and established artists alike gather in this inspiring space above Pilars Martini to hone their craft, demonstrate their talent and take the Winter Garden art scene to new heights. Equal parts

entertainment and inspiration, a visit to The Loft on Plant is just plain good for the soul. Join us to discover the talented neighbors you never knew you had. Because when it comes to putting on a good show on Plant Street, things are looking up. Cocktails from Pilars -Food from Market to Table - Music Thursday 7-10p, Friday & Saturday 8-11p and Sunday 5-8p and other special events posted online at https://pilarsmartini.ticketleap.com

This week at Pilars Loft! 🎵🍸
06/23/2026

This week at Pilars Loft! 🎵🍸

THIS THURSDAY: Pilars Loft welcomes Guest Host Trudie Petersen and Pianist Michael Mastroianni to Billy Flanigan’s Singe...
06/22/2026

THIS THURSDAY: Pilars Loft welcomes Guest Host Trudie Petersen and Pianist Michael Mastroianni to Billy Flanigan’s Singers’ Open Mic Night!

HAPPY FATHER’S DAY! We hope you’ll join us today for great music, cocktails, and cuisine! Pilars Loft is excited to welc...
06/21/2026

HAPPY FATHER’S DAY! We hope you’ll join us today for great music, cocktails, and cuisine! Pilars Loft is excited to welcome Juilliard’s PRESTON RUPERT (Trumpet) for the first hour (5-6pm), along with the Pilars House Trio: Richard Drexler (Piano), Charlie Silva (Bass), and Greg Parnell (Drums). Then, enjoy the OPEN JAM until 8pm.

MARK YOUR CALENDAR for Michelle Mailhot (Vocals), Ed Krout (Piano/Hammond B3), Chuck Archard (Bass), and Jeremy Kataleni...
06/20/2026

MARK YOUR CALENDAR for Michelle Mailhot (Vocals), Ed Krout (Piano/Hammond B3), Chuck Archard (Bass), and Jeremy Katalenic (Drums) in Pilars Loft on Saturday, June 27th!

Enjoy Pilars’ hand-crafted cocktails, premium wines and beer, and great food from Market To Table. 🍸🎵

Sunday's Jazz Jam, the Father - Son combo of Preston & Jeff Rupert are the First Hour Feature. Richard Drexler, Charlie...
06/20/2026

Sunday's Jazz Jam, the Father - Son combo of Preston & Jeff Rupert are the First Hour Feature. Richard Drexler, Charlie Silva & Greg Parnell complete the band for a special treat for all the fathers. Come one, come all - relax and enjoy the jam. Drinks, Dinner & Dad.

Plan to join us TONIGHT for exceptional live music by trumpeter/composer Scott Dickinson with Bob Thornton (Piano), Tho...
06/20/2026

Plan to join us TONIGHT for exceptional live music by trumpeter/composer Scott Dickinson with Bob Thornton (Piano), Thomas Milovac (Bass), and Jeremy Katalenic (Drums) from 8PM-11PM! 🎺🎶🍸

501 Band Returns Friday, June 26th with Jim Gentry, Richie Compton, Michael Gironda (Guitars), Dru Betts (Drums), Mike L...
06/19/2026

501 Band Returns Friday, June 26th with Jim Gentry, Richie Compton, Michael Gironda (Guitars), Dru Betts (Drums), Mike Loman (Keys), and the 501 Horns! Bluesy, funky, fun!

Join us TONIGHT at 8PM for Dimas Sánchez Afro Latin Jazz Project (Drums) with Mariano Morales (Piano), Jochy Rodriquez (...
06/19/2026

Join us TONIGHT at 8PM for Dimas Sánchez Afro Latin Jazz Project (Drums) with Mariano Morales (Piano), Jochy Rodriquez (Trumpet), Jorge L. Malave (Sax), David Ernesto (Bass), Anthony Velázquez (Percussion), and Guest Vocalist Ruti Silva!

TONIGHT Pilars Loft welcomes Guest Host Trudie Petersen and Pianist Harrison Light to Billy Flanigan’s Singers’ Open Mic...
06/18/2026

TONIGHT Pilars Loft welcomes Guest Host Trudie Petersen and Pianist Harrison Light to Billy Flanigan’s Singers’ Open Mic Night! We hope to see you there...

Father’s Day is this Sunday! Why not bring Dad or that special someone to our Sunday Jazz Jam? Great music, cocktails, a...
06/17/2026

Father’s Day is this Sunday! Why not bring Dad or that special someone to our Sunday Jazz Jam? Great music, cocktails, and cuisine! Pilars Loft is excited to welcome trumpeter PRESTON RUPERT for the first hour (5-6pm), along with the Pilars House Trio: Richard Drexler (Piano), Charlie Silva (Bass), and Greg Parnell (Drums). Then, enjoy the OPEN JAM until 8pm.

Preston Rupert moved to New York City in 2024 to continue his study of music at The Juilliard School. Coming from a musical family (including Pilars visiting artist, Jeff Rupert), he has been immersed in music his entire life and has been mentored by several notable visionaries of Jazz. Rupert has a clear vision of his place in the jazz continuum and as an evolving artist. He has performed in several notable venues around the world, including Carnegie Hall, The Concertgebouw in Amsterdam, and Royal Albert Hall, to name a few. Rupert has also participated in The Vail Jazz Workshop, The National Youth Orchestra Jazz Orchestra, and was a winner with distinction for YoungArts in Jazz.

Address

146 W Plant Street Suite 210
Winter Garden, FL
34787

Opening Hours

Thursday 6pm - 11pm
Friday 7pm - 12am
Saturday 7pm - 12am
Sunday 4pm - 9pm

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