Tantric 25th Anniversary
Nov
18

Tantric 25th Anniversary

Celebrating 25 years - Tantric brings their anniversary tour to Jessie’s! Get your tickets ahead of time at the link below!

Featuring guests: Behind the Haze, Who On Earth, Mike Lee and Frank Fletcher!

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Peace Train Karaoke
Nov
19

Peace Train Karaoke

https://fb.me/e/13BTyBwoV

Join the musical journey at Jessie's Lounge with Peace Train Karaoke!

Departure is every Thursday at 9 PM, so gear up to sing your favorite tunes and groove along with our stellar playlist and a drink selection that's right on point. Don't miss out on the chance to harmonize in downtown Winter Haven!

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The Jam with No Name w/ Frankie
Nov
25

The Jam with No Name w/ Frankie

Every Wednesday at 𝟳 𝗣𝗠, don't miss 𝗧𝗵𝗲 𝗝𝗮𝗺 𝘄𝗶𝘁𝗵 𝗡𝗼 𝗡𝗮𝗺𝗲, hosted by Frankie at Jessie's Lounge in the heart of downtown Winter Haven!

Bring your instruments, your talent, or just your love for music. Hop on stage and perform for the crowd! You don't have to be a pro – all skill levels are welcome. It's all about the fun, the energy, and the creativity!

While you're here, be sure to enjoy some great drinks at the bar to complement your musical experience. It's the ultimate midweek combination of great music and drinks in downtown Winter Haven. See you there!

See less

View Event →
Peace Train Karaoke
Nov
26

Peace Train Karaoke

https://fb.me/e/13BTyBwoV

Join the musical journey at Jessie's Lounge with Peace Train Karaoke!

Departure is every Thursday at 9 PM, so gear up to sing your favorite tunes and groove along with our stellar playlist and a drink selection that's right on point. Don't miss out on the chance to harmonize in downtown Winter Haven!

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The Sirens of Sunshine Tour | Paralandra, Major Moment, Pulsifier, Ignescent
Dec
8

The Sirens of Sunshine Tour | Paralandra, Major Moment, Pulsifier, Ignescent

Jessie’s Lounge Presents:
The Sirens of Sunshine Tour 2026 feat.

Paralandra
Major Moment
Pulsifier
and more TBA

Tue. 12/08 I Doors 5pm I Show 6pm I All Ages I Tickets $18 ADV

Since their 2013 inception, Paralandra has hit the ground running. The band hails from Springfield, MO and is led by father and daughter, Paul and Casandra Carson. They were later joined by local friends and musicians, bassist, Sawyer Rikard, and drummer, Dakota Watson, to form their dream lineup. 2014's self-made album "Rise Up" launched the band into the forefront of the rock scene attracting the attention of Legend Recordings. Under the umbrella of Legend, they have released "All Fall Down" (2016) and "Ascension" (2018) which feature singles “All Fall Down”, “Back to Life” and “Killer Queen”. In 2019, they released stand-alone single “Love Will Win” which gained Mainstream radio play. In 2021, they cut a full length album “Street Magic” with world-renowned producer, Michael “Elvis” Baskette (Alter Bridge, Slash, Sevendust, Mammoth WVH). Multiple singles raced up the billboard charts including "Despicable", “Only Human” and “For the Record”. In 2023, they returned to Elvis’ studio, and recorded another full length album titled “The Body Electric” which was released in 2024. In 2025, Paralandra decided to switch things up a bit, and released a holiday EP titled “Hallomas” in 2025, featuring reimagined Halloween and Christmas songs.

Boston-based pop metal band Major Moment is known for their intense and cinematic sound that blends heavy guitar riffs, modern production, and melodic vocals. What sets them apart is their unique use of both male and female clean and extreme vocals that create a harmonious blend of contrasting styles. The band draws inspiration from their personal experiences to create music that speaks to their listeners and encourages them to pursue their dreams and live a life of purpose.

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Peace Train Karaoke
Aug
27

Peace Train Karaoke

https://fb.me/e/13BTyBwoV

Join the musical journey at Jessie's Lounge with Peace Train Karaoke!

Departure is every Thursday at 9 PM, so gear up to sing your favorite tunes and groove along with our stellar playlist and a drink selection that's right on point. Don't miss out on the chance to harmonize in downtown Winter Haven!

View Event →
Peace Train Karaoke
Aug
20

Peace Train Karaoke

https://fb.me/e/13BTyBwoV

Join the musical journey at Jessie's Lounge with Peace Train Karaoke!

Departure is every Thursday at 9 PM, so gear up to sing your favorite tunes and groove along with our stellar playlist and a drink selection that's right on point. Don't miss out on the chance to harmonize in downtown Winter Haven!

View Event →
The Jam with No Name w/ Frankie
Aug
19

The Jam with No Name w/ Frankie

Every Wednesday at 𝟳 𝗣𝗠, don't miss 𝗧𝗵𝗲 𝗝𝗮𝗺 𝘄𝗶𝘁𝗵 𝗡𝗼 𝗡𝗮𝗺𝗲, hosted by Frankie at Jessie's Lounge in the heart of downtown Winter Haven!

Bring your instruments, your talent, or just your love for music. Hop on stage and perform for the crowd! You don't have to be a pro – all skill levels are welcome. It's all about the fun, the energy, and the creativity!

While you're here, be sure to enjoy some great drinks at the bar to complement your musical experience. It's the ultimate midweek combination of great music and drinks in downtown Winter Haven. See you there!

See less

View Event →
Peace Train Karaoke
Aug
13

Peace Train Karaoke

https://fb.me/e/13BTyBwoV

Join the musical journey at Jessie's Lounge with Peace Train Karaoke!

Departure is every Thursday at 9 PM, so gear up to sing your favorite tunes and groove along with our stellar playlist and a drink selection that's right on point. Don't miss out on the chance to harmonize in downtown Winter Haven!

View Event →
The Jam with No Name w/ Frankie
Aug
12

The Jam with No Name w/ Frankie

Every Wednesday at 𝟳 𝗣𝗠, don't miss 𝗧𝗵𝗲 𝗝𝗮𝗺 𝘄𝗶𝘁𝗵 𝗡𝗼 𝗡𝗮𝗺𝗲, hosted by Frankie at Jessie's Lounge in the heart of downtown Winter Haven!

Bring your instruments, your talent, or just your love for music. Hop on stage and perform for the crowd! You don't have to be a pro – all skill levels are welcome. It's all about the fun, the energy, and the creativity!

While you're here, be sure to enjoy some great drinks at the bar to complement your musical experience. It's the ultimate midweek combination of great music and drinks in downtown Winter Haven. See you there!

See less

View Event →
Peace Train Karaoke
Aug
6

Peace Train Karaoke

https://fb.me/e/13BTyBwoV

Join the musical journey at Jessie's Lounge with Peace Train Karaoke!

Departure is every Thursday at 9 PM, so gear up to sing your favorite tunes and groove along with our stellar playlist and a drink selection that's right on point. Don't miss out on the chance to harmonize in downtown Winter Haven!

View Event →
The Jam with No Name w/ Frankie
Aug
5

The Jam with No Name w/ Frankie

Every Wednesday at 𝟳 𝗣𝗠, don't miss 𝗧𝗵𝗲 𝗝𝗮𝗺 𝘄𝗶𝘁𝗵 𝗡𝗼 𝗡𝗮𝗺𝗲, hosted by Frankie at Jessie's Lounge in the heart of downtown Winter Haven!

Bring your instruments, your talent, or just your love for music. Hop on stage and perform for the crowd! You don't have to be a pro – all skill levels are welcome. It's all about the fun, the energy, and the creativity!

While you're here, be sure to enjoy some great drinks at the bar to complement your musical experience. It's the ultimate midweek combination of great music and drinks in downtown Winter Haven. See you there!

See less

View Event →
DJ Melvin
Jul
31

DJ Melvin

Don’t miss DJ Melvin at Jessie's at 9 PM!

He’ll be dropping the best 2000's break beats and electrifying EDM remixes. Bring your friends and let’s make this an unforgettable night!

View Event →
Peace Train Karaoke
Jul
30

Peace Train Karaoke

https://fb.me/e/13BTyBwoV

Join the musical journey at Jessie's Lounge with Peace Train Karaoke!

Departure is every Thursday at 9 PM, so gear up to sing your favorite tunes and groove along with our stellar playlist and a drink selection that's right on point. Don't miss out on the chance to harmonize in downtown Winter Haven!

View Event →
The Jam with No Name w/ Frankie
Jul
29

The Jam with No Name w/ Frankie

Every Wednesday at 𝟳 𝗣𝗠, don't miss 𝗧𝗵𝗲 𝗝𝗮𝗺 𝘄𝗶𝘁𝗵 𝗡𝗼 𝗡𝗮𝗺𝗲, hosted by Frankie at Jessie's Lounge in the heart of downtown Winter Haven!

Bring your instruments, your talent, or just your love for music. Hop on stage and perform for the crowd! You don't have to be a pro – all skill levels are welcome. It's all about the fun, the energy, and the creativity!

While you're here, be sure to enjoy some great drinks at the bar to complement your musical experience. It's the ultimate midweek combination of great music and drinks in downtown Winter Haven. See you there!

See less

View Event →
Peace Train Karaoke
Jul
23

Peace Train Karaoke

https://fb.me/e/13BTyBwoV

Join the musical journey at Jessie's Lounge with Peace Train Karaoke!

Departure is every Thursday at 9 PM, so gear up to sing your favorite tunes and groove along with our stellar playlist and a drink selection that's right on point. Don't miss out on the chance to harmonize in downtown Winter Haven!

View Event →
The Jam with No Name w/ Frankie
Jul
22

The Jam with No Name w/ Frankie

Every Wednesday at 𝟳 𝗣𝗠, don't miss 𝗧𝗵𝗲 𝗝𝗮𝗺 𝘄𝗶𝘁𝗵 𝗡𝗼 𝗡𝗮𝗺𝗲, hosted by Frankie at Jessie's Lounge in the heart of downtown Winter Haven!

Bring your instruments, your talent, or just your love for music. Hop on stage and perform for the crowd! You don't have to be a pro – all skill levels are welcome. It's all about the fun, the energy, and the creativity!

While you're here, be sure to enjoy some great drinks at the bar to complement your musical experience. It's the ultimate midweek combination of great music and drinks in downtown Winter Haven. See you there!

See less

View Event →
DJ Melvin
Jul
17

DJ Melvin

Don’t miss DJ Melvin at Jessie's at 9 PM!

He’ll be dropping the best 2000's break beats and electrifying EDM remixes. Bring your friends and let’s make this an unforgettable night!

View Event →
Peace Train Karaoke
Jul
16

Peace Train Karaoke

https://fb.me/e/13BTyBwoV

Join the musical journey at Jessie's Lounge with Peace Train Karaoke!

Departure is every Thursday at 9 PM, so gear up to sing your favorite tunes and groove along with our stellar playlist and a drink selection that's right on point. Don't miss out on the chance to harmonize in downtown Winter Haven!

View Event →
The Jam with No Name w/ Frankie
Jul
15

The Jam with No Name w/ Frankie

Every Wednesday at 𝟳 𝗣𝗠, don't miss 𝗧𝗵𝗲 𝗝𝗮𝗺 𝘄𝗶𝘁𝗵 𝗡𝗼 𝗡𝗮𝗺𝗲, hosted by Frankie at Jessie's Lounge in the heart of downtown Winter Haven!

Bring your instruments, your talent, or just your love for music. Hop on stage and perform for the crowd! You don't have to be a pro – all skill levels are welcome. It's all about the fun, the energy, and the creativity!

While you're here, be sure to enjoy some great drinks at the bar to complement your musical experience. It's the ultimate midweek combination of great music and drinks in downtown Winter Haven. See you there!

See less

View Event →
Gerry Williams
Jul
10

Gerry Williams

Winter Haven! Are you ready to get funky?? Well you’ll have your chance, July 25th at 8pm Winter Haven’s own Gerry William will be rockin the block!

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Peace Train Karaoke
Jul
9

Peace Train Karaoke

https://fb.me/e/13BTyBwoV

Join the musical journey at Jessie's Lounge with Peace Train Karaoke!

Departure is every Thursday at 9 PM, so gear up to sing your favorite tunes and groove along with our stellar playlist and a drink selection that's right on point. Don't miss out on the chance to harmonize in downtown Winter Haven!

View Event →
The Jam with No Name w/ Frankie
Jul
8

The Jam with No Name w/ Frankie

Every Wednesday at 𝟳 𝗣𝗠, don't miss 𝗧𝗵𝗲 𝗝𝗮𝗺 𝘄𝗶𝘁𝗵 𝗡𝗼 𝗡𝗮𝗺𝗲, hosted by Frankie at Jessie's Lounge in the heart of downtown Winter Haven!

Bring your instruments, your talent, or just your love for music. Hop on stage and perform for the crowd! You don't have to be a pro – all skill levels are welcome. It's all about the fun, the energy, and the creativity!

While you're here, be sure to enjoy some great drinks at the bar to complement your musical experience. It's the ultimate midweek combination of great music and drinks in downtown Winter Haven. See you there!

See less

View Event →
DJ Melvin
Jul
3

DJ Melvin

Don’t miss DJ Melvin at Jessie's at 9 PM!

He’ll be dropping the best 2000's break beats and electrifying EDM remixes. Bring your friends and let’s make this an unforgettable night!

View Event →
Peace Train Karaoke
Jul
2

Peace Train Karaoke

https://fb.me/e/13BTyBwoV

Join the musical journey at Jessie's Lounge with Peace Train Karaoke!

Departure is every Thursday at 9 PM, so gear up to sing your favorite tunes and groove along with our stellar playlist and a drink selection that's right on point. Don't miss out on the chance to harmonize in downtown Winter Haven!

View Event →
The Jam with No Name w/ Frankie
Jul
1

The Jam with No Name w/ Frankie

Every Wednesday at 𝟳 𝗣𝗠, don't miss 𝗧𝗵𝗲 𝗝𝗮𝗺 𝘄𝗶𝘁𝗵 𝗡𝗼 𝗡𝗮𝗺𝗲, hosted by Frankie at Jessie's Lounge in the heart of downtown Winter Haven!

Bring your instruments, your talent, or just your love for music. Hop on stage and perform for the crowd! You don't have to be a pro – all skill levels are welcome. It's all about the fun, the energy, and the creativity!

While you're here, be sure to enjoy some great drinks at the bar to complement your musical experience. It's the ultimate midweek combination of great music and drinks in downtown Winter Haven. See you there!

See less

View Event →
Peace Train Karaoke
Jun
25

Peace Train Karaoke

https://fb.me/e/13BTyBwoV

Join the musical journey at Jessie's Lounge with Peace Train Karaoke!

Departure is every Thursday at 9 PM, so gear up to sing your favorite tunes and groove along with our stellar playlist and a drink selection that's right on point. Don't miss out on the chance to harmonize in downtown Winter Haven!

View Event →
The Jam with No Name w/ Frankie
Jun
24

The Jam with No Name w/ Frankie

Every Wednesday at 𝟳 𝗣𝗠, don't miss 𝗧𝗵𝗲 𝗝𝗮𝗺 𝘄𝗶𝘁𝗵 𝗡𝗼 𝗡𝗮𝗺𝗲, hosted by Frankie at Jessie's Lounge in the heart of downtown Winter Haven!

Bring your instruments, your talent, or just your love for music. Hop on stage and perform for the crowd! You don't have to be a pro – all skill levels are welcome. It's all about the fun, the energy, and the creativity!

While you're here, be sure to enjoy some great drinks at the bar to complement your musical experience. It's the ultimate midweek combination of great music and drinks in downtown Winter Haven. See you there!

See less

View Event →
Peace Train Karaoke
Jun
18

Peace Train Karaoke

https://fb.me/e/13BTyBwoV

Join the musical journey at Jessie's Lounge with Peace Train Karaoke!

Departure is every Thursday at 9 PM, so gear up to sing your favorite tunes and groove along with our stellar playlist and a drink selection that's right on point. Don't miss out on the chance to harmonize in downtown Winter Haven!

View Event →
The Jam with No Name w/ Frankie
Jun
17

The Jam with No Name w/ Frankie

Every Wednesday at 𝟳 𝗣𝗠, don't miss 𝗧𝗵𝗲 𝗝𝗮𝗺 𝘄𝗶𝘁𝗵 𝗡𝗼 𝗡𝗮𝗺𝗲, hosted by Frankie at Jessie's Lounge in the heart of downtown Winter Haven!

Bring your instruments, your talent, or just your love for music. Hop on stage and perform for the crowd! You don't have to be a pro – all skill levels are welcome. It's all about the fun, the energy, and the creativity!

While you're here, be sure to enjoy some great drinks at the bar to complement your musical experience. It's the ultimate midweek combination of great music and drinks in downtown Winter Haven. See you there!

See less

View Event →
Peace Train Karaoke
Jun
11

Peace Train Karaoke

https://fb.me/e/13BTyBwoV

Join the musical journey at Jessie's Lounge with Peace Train Karaoke!

Departure is every Thursday at 9 PM, so gear up to sing your favorite tunes and groove along with our stellar playlist and a drink selection that's right on point. Don't miss out on the chance to harmonize in downtown Winter Haven!

View Event →
The Jam with No Name w/ Frankie
Jun
10

The Jam with No Name w/ Frankie

Every Wednesday at 𝟳 𝗣𝗠, don't miss 𝗧𝗵𝗲 𝗝𝗮𝗺 𝘄𝗶𝘁𝗵 𝗡𝗼 𝗡𝗮𝗺𝗲, hosted by Frankie at Jessie's Lounge in the heart of downtown Winter Haven!

Bring your instruments, your talent, or just your love for music. Hop on stage and perform for the crowd! You don't have to be a pro – all skill levels are welcome. It's all about the fun, the energy, and the creativity!

While you're here, be sure to enjoy some great drinks at the bar to complement your musical experience. It's the ultimate midweek combination of great music and drinks in downtown Winter Haven. See you there!

See less

View Event →
Peace Train Karaoke
Jun
4

Peace Train Karaoke

https://fb.me/e/13BTyBwoV

Join the musical journey at Jessie's Lounge with Peace Train Karaoke!

Departure is every Thursday at 9 PM, so gear up to sing your favorite tunes and groove along with our stellar playlist and a drink selection that's right on point. Don't miss out on the chance to harmonize in downtown Winter Haven!

View Event →
The Jam with No Name w/ Frankie
Jun
3

The Jam with No Name w/ Frankie

Every Wednesday at 𝟳 𝗣𝗠, don't miss 𝗧𝗵𝗲 𝗝𝗮𝗺 𝘄𝗶𝘁𝗵 𝗡𝗼 𝗡𝗮𝗺𝗲, hosted by Frankie at Jessie's Lounge in the heart of downtown Winter Haven!

Bring your instruments, your talent, or just your love for music. Hop on stage and perform for the crowd! You don't have to be a pro – all skill levels are welcome. It's all about the fun, the energy, and the creativity!

While you're here, be sure to enjoy some great drinks at the bar to complement your musical experience. It's the ultimate midweek combination of great music and drinks in downtown Winter Haven. See you there!

See less

View Event →
Peace Train Karaoke
May
28

Peace Train Karaoke

https://fb.me/e/13BTyBwoV

Join the musical journey at Jessie's Lounge with Peace Train Karaoke!

Departure is every Thursday at 9 PM, so gear up to sing your favorite tunes and groove along with our stellar playlist and a drink selection that's right on point. Don't miss out on the chance to harmonize in downtown Winter Haven!

View Event →