Wallet User Shopping-cart
Wallet User Shopping-cart

Nightly Entertainment

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.

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.
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

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 May 18, 2026
5:00 pm - 9:00 pm
Sawgrass Grove
766 Marilee Place, The Villages, FL 34785

Paisley Craze

Paisley Craze is a Rockadelic '60s music anthology band from Sarasota FL! Celebrating the music.
Mon May 18, 2026
5:00 pm - 9:00 pm
Spanish Springs Town Square®
1051 Main St, The Villages, FL 32159

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
Anita Drink Band Photos

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.
Mon May 18, 2026
5:00 pm - 9:00 pm
Brownwood Paddock Square®
2726 Brownwood Blvd, The Villages, FL 32163

X Girlfriend

This fierce, female-fronted crew brings the party, the attitude, and the anthems of rock and pop-punk hits!
Mon May 18, 2026
5:00 pm - 9:00 pm
Eastport (Main Stage)
7025 Central Lake Dr The Villages, FL 34762

Trivia Tuesday

Join us at Sawgrass Grove every Tuesday for your chance to win a variety of prizes! Free admission, no ticket required.
Tue May 19, 2026
12:00 pm - 2:00 pm
Sawgrass Grove
766 Marilee Place, The Villages, FL 34785

SSnakeyez

Classic/Southern rock! 3 piece band of high energy!
Tue May 19, 2026
5:00 pm - 9:00 pm
Spanish Springs Town Square®
1051 Main St, The Villages, FL 32159

Steve Hogie Band

Classic rock and timeless tunes.
Tue May 19, 2026
5:00 pm - 9:00 pm
Sawgrass Grove
766 Marilee Place, The Villages, FL 34785

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

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.
Tue May 19, 2026
5:00 pm - 9:00 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.
Wed May 20, 2026
5:00 pm - 9:00 pm
Spanish Springs Town Square®
1051 Main St, The Villages, FL 32159

Justin Heet Band

Rock at its finest! This band doesn't hold back. Come out and party with this great rock band!
Wed May 20, 2026
5:00 pm - 9:00 pm
Sawgrass Grove
766 Marilee Place, The Villages, FL 34785
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

Penta

Penta is an exceptional Daytona Beach rock, blues, and funk band.
Wed May 20, 2026
5:00 pm - 9:00 pm
Brownwood Paddock Square®
2726 Brownwood Blvd, The Villages, FL 32163

The Alan Ross Karaoke Roadshow

Karaoke with host Alan Ross brings a spotlight to your inner star. Enjoy a wide variety of songs with some guidance from our host, who knows how to keep the energy just right to make every performance feel like a hit!
Thu May 21, 2026
12:00 pm - 2:00 pm
Sawgrass Grove
766 Marilee Place, The Villages, FL 34785
No event found!
Load More