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Nightly Entertainment: Lake Sumter Landing Market Square®

PLEASE NOTE: This summer, Jun. 01 through Aug. 31, nightly entertainment hours will shift from 5:00 PM – 9:00 PM to 6:00 PM – 10:00 PM.
Happy Hour will remain unchanged from 5:00 PM – 6:00 PM.

This adjustment will help avoid the peak summer heat and weather delays while still delivering a full four hours of live entertainment each evening.

Select an option below to download the Lake Sumter Landing Market Square® calendar or the full calendar.

ENT395 Entertainment Schedule Logo Blocks-LSL
A button that includes an image of a dancing crowd and invites you to "Download Full Calendar" for Nightly Entertainment.

WARNING:
Strobing and lighting will be used during scheduled entertainment that may not be suitable for individuals with conditions that include sensitivity to light.

WARNING:
Strobing and lighting will be used during scheduled entertainment that may not be suitable for
individuals with conditions that include sensitivity to light.

**All events and performances subject to change**

May 2026

Big Chief | Car Show 5:00 PM – 8:00 PM

Big Chief mixes R&B with Mardi Gras party music that makes it impossible to sit down. Always a crowd favorite!
Mon May 18, 2026
5:00 pm - 9:00 pm
Lake Sumter Landing Market Square®
1020 Lake Sumter Landing, The Villages, FL 32162

Ember Road

With roots in Southern rock and country, Ember Road delivers groove, soul, and a little reggae twist to fan-favorite songs across the decades.
Tue May 19, 2026
5:00 pm - 9:00 pm
Lake Sumter Landing Market Square®
1020 Lake Sumter Landing, The Villages, FL 32162
Think Big Band, a group of 6, stand together smiling.

Think Big Band

Think Big Band is not just any ordinary "live" band. Whether it be classic rock, Motown, blues, country, or your favorite dance tunes, we play it all!
Wed May 20, 2026
5:00 pm - 9:00 pm
Lake Sumter Landing Market Square®
1020 Lake Sumter Landing, The Villages, FL 32162

Pavani’s Band

From the streets of Rio to the subways of Manhattan, Pavani’s Band delivers a dynamic blend of raw talent and timeless hits, spanning decades of '70s and '80s.
Thu May 21, 2026
5:00 pm - 9:00 pm
Lake Sumter Landing Market Square®
1020 Lake Sumter Landing, The Villages, FL 32162

Osaka Fall

Uncovered Hits, Unforgettable Vibes. Osaka Fall sets itself apart with a setlist you won’t hear anywhere else. From rare old-school jams to glam rock, funk, modern pop, and soulful love songs, they create a musical experience like no other.
Fri May 22, 2026
5:00 pm - 9:00 pm
Lake Sumter Landing Market Square®
1020 Lake Sumter Landing, The Villages, FL 32162

Swing Theory

Step back to the '20s, '30s, '40s, big band era. This 7 piece band covers the best of jazz, blues, Latin, and funk!
Sat May 23, 2026
5:00 pm - 9:00 pm
Lake Sumter Landing Market Square®
1020 Lake Sumter Landing, The Villages, FL 32162

Sheila & The Sound

From Aretha to Journey, Sheila & The Sound bring the power, passion, and pipes to turn every stage into a retro-fueled dance floor.
Sun May 24, 2026
5:00 pm - 9:00 pm
Lake Sumter Landing Market Square®
1020 Lake Sumter Landing, The Villages, FL 32162

Stella Beat

Stella Beat is an energetic Latin/Top 40 party band based in Orlando, FL.
Mon May 25, 2026
5:00 pm - 9:00 pm
Lake Sumter Landing Market Square®
1020 Lake Sumter Landing, The Villages, FL 32162

Scooter The DJ

Audience participation is required! Popular dances and Scooter Originals!
Tue May 26, 2026
5:00 pm - 9:00 pm
Lake Sumter Landing Market Square®
1020 Lake Sumter Landing, The Villages, FL 32162

Jerico

Leaning to the southern side of rock, Jerico celebrates the sounds of the last 6 decades!
Wed May 27, 2026
5:00 pm - 9:00 pm
Lake Sumter Landing Market Square®
1020 Lake Sumter Landing, The Villages, FL 32162

Southbound

Southbound is a top shelf country/party band from Orlando, Fl. This experienced band combines powerful lead vocals, harmonies and stellar instrumentalists.
Thu May 28, 2026
5:00 pm - 9:00 pm
Lake Sumter Landing Market Square®
1020 Lake Sumter Landing, The Villages, FL 32162
Members of The Brothers Jukebox in a v formation. The lead holds a guitar.

The Brothers Jukebox

Spinning country gold and classic rock with heart. The Brothers Jukebox delivers down-home harmonies, front-porch memories, and the kind of sound that keeps life sweet, smooth, and simple.
Fri May 29, 2026
5:00 pm - 9:00 pm
Lake Sumter Landing Market Square®
1020 Lake Sumter Landing, The Villages, FL 32162

Rocky and The Rollers

An absolute Villages favorite. Rocky and The Rollers have 27 years performing in The Villages and their wide range of high energy music from all eras and genres will keep you excited and engaged throughout the performance.
Sat May 30, 2026
5:00 pm - 9:00 pm
Lake Sumter Landing Market Square®
1020 Lake Sumter Landing, The Villages, FL 32162

Greg Warren Band

High energy country, classic rock, rock and dance band. We like to keep you dancing all night!
Sun May 31, 2026
5:00 pm - 9:00 pm
Lake Sumter Landing Market Square®
1020 Lake Sumter Landing, The Villages, FL 32162
No event found!