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Nightly Entertainment

PLEASE NOTE: This summer, Jun. 01 through Sep. 30, nightly entertainment hours will shift from 5:00 PM – 9:00 PM to 6:00 PM – 10:00 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.

Choose a location below to download the corresponding calendar.

Blue rounded button with white text reading “EASTPORT” at the top and larger curved “Eastport” centered.
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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**

August 2026

Eighteen87

Named for their roots and built for the stage, Eighteen87 cranks out decades of iconic hits with a fresh twist and a Florida groove you’ll feel in your bones.
Mon Aug 31, 2026
6:00 pm - 10:00 pm
Spanish Springs Town Square®
1051 Main St, The Villages, FL 32159

Billy Buchanan & His Rock N’ Soul Revue

Soul, early rock, and blues from the '50s to the '80s and beyond!
Mon Aug 31, 2026
6:00 pm - 10:00 pm
Lake Sumter Landing Market Square®
1020 Lake Sumter Landing, The Villages, FL 32162

Justin Heet Band

Rock at its finest! This band doesn't hold back. Come out and party with this great rock band!
Mon Aug 31, 2026
6:00 pm - 10:00 pm
Brownwood Paddock Square®
2726 Brownwood Blvd, The Villages, FL 32163

Stella Beat

Stella Beat is an energetic Latin/Top 40 party band based in Orlando, FL.
Mon Aug 31, 2026
6:00 pm - 10:00 pm
Eastport
7025 Central Lake Dr The Villages, FL 34762

Boozy Bingo at Sawgrass Grove

Not your grandparent's bingo! From music, to movies, we ask the questions as you place your chips on the answer! Click here to view details.
Mon Aug 31, 2026
6:00 pm - 10:00 pm
Sawgrass Grove
766 Marilee Place, The Villages, FL 34785
September 2026

Trivia Tuesday

Join us at Sawgrass Grove every Tuesday for your chance to win a variety of prizes! Free admission, no ticket required.
Tue Sep 01, 2026
12:00 pm - 2:00 pm
Sawgrass Grove
766 Marilee Place, The Villages, FL 34785

Acoustic Blue

Authentic acoustic experience with a variety of music and amazing paired vocals!
Tue Sep 01, 2026
6:00 pm - 10:00 pm
Sawgrass Grove
766 Marilee Place, The Villages, FL 34785

5.0.1.

5.0.1. lets the MUSIC come first. Playing the best of the Blues, Soul & Classic Rock Music from the '60s and '70s.
Tue Sep 01, 2026
6:00 pm - 10:00 pm
Brownwood Paddock Square®
2726 Brownwood Blvd, The Villages, FL 32163

Slickwood

A Central Florida jamgrass band blending Americana, bluegrass, and folk with exceptional harmonies and energetic instrumentation.
Tue Sep 01, 2026
6:00 pm - 10:00 pm
Lake Sumter Landing Market Square®
1020 Lake Sumter Landing, The Villages, FL 32162

Latin Ambition

Delivering a fast-paced, DJ style approach to live music - offering SOMETHING FOR EVERYONE like no one else can with unexpected twists and turns to excite the crowd every step of the way.
Tue Sep 01, 2026
6:00 pm - 10:00 pm
Spanish Springs Town Square®
1051 Main St, The Villages, FL 32159

Anita Drink Band

Anita Drink Band is a high-energy variety band bringing the best of rock ’n’ roll from the ’60s to today, plus fan-favorite originals, soulful Christian selections, country hits, and blues grooves that keep every crowd singing along and tapping their feet.
Wed Sep 02, 2026
6:00 pm - 10:00 pm
Sawgrass Grove
766 Marilee Place, The Villages, FL 34785

Street Talk

Central Florida's premier dance and party band. Street Talk is a group of musicians dedicated to putting on a great show! Classic rock, '80s and earlier, Top 40.
Wed Sep 02, 2026
6:00 pm - 10:00 pm
Eastport
7025 Central Lake Dr The Villages, FL 34762

Live Effect

High energy dance band with tight vocal harmonies performing ALL the hits from yesterday & today!
Wed Sep 02, 2026
6:00 pm - 10:00 pm
Brownwood Paddock Square®
2726 Brownwood Blvd, The Villages, FL 32163

Big Chief

Big Chief mixes R&B with Mardi Gras party music that makes it impossible to sit down. Always a crowd favorite!
Wed Sep 02, 2026
6:00 pm - 10:00 pm
Lake Sumter Landing Market Square®
1020 Lake Sumter Landing, The Villages, FL 32162

Fancy Reagan

Fancy Reagan is a female-fronted non-stop '80s dance party like no other! Featuring some of the best musicians in Central Florida. Nobody puts the '80s in a corner!
Wed Sep 02, 2026
6:00 pm - 10:00 pm
Spanish Springs Town Square®
1051 Main St, The Villages, FL 32159
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