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Nightly Entertainment: Brownwood Paddock 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 Brownwood Paddock Square® calendar or the full calendar.

ENT395 Entertainment Schedule Logo Blocks-Brownwood
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

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 May 27, 2026
5:00 pm - 9:00 pm
Brownwood Paddock Square®
2726 Brownwood Blvd, The Villages, FL 32163

Hayfire

A fun, energetic country band with superb vocals! Hayfire is one of The Villages' best and dubbed one of Orlando Weekly's Best Cover Bands.
Thu May 28, 2026
5:00 pm - 9:00 pm
Brownwood Paddock Square®
2726 Brownwood Blvd, The Villages, FL 32163

Uncle Bob’s Rock Shop

Live in Concert – This is Uncle Bob's Rock Shop. Playing iconic classic rock hits with a genuine concert feel.
Fri May 29, 2026
5:00 pm - 9:00 pm
Brownwood Paddock Square®
2726 Brownwood Blvd, The Villages, FL 32163

Cable Cars

Cable Cars is a dynamic cover band ready to transport audiences to the hits of decades past and today!
Sat May 30, 2026
5:00 pm - 9:00 pm
Brownwood Paddock Square®
2726 Brownwood Blvd, The Villages, FL 32163

Bar Fly

Bar Fly raises the bar with a buzz-worthy mix of rock, soul, and swagger playing hits from the '70s, the '80s and beyond!
Sun May 31, 2026
5:00 pm - 9:00 pm
Brownwood Paddock Square®
2726 Brownwood Blvd, The Villages, FL 32163
June 2026

Greg Warren Band

High energy country, classic rock, rock and dance band. We like to keep you dancing all night!
Mon Jun 01, 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.
Tue Jun 02, 2026
6:00 pm - 10:00 pm
Brownwood Paddock Square®
2726 Brownwood Blvd, The Villages, FL 32163

Scooter The DJ

Audience participation is required! Popular dances and Scooter Originals!
Wed Jun 03, 2026
6:00 pm - 10:00 pm
Brownwood Paddock Square®
2726 Brownwood Blvd, The Villages, FL 32163

Second Slice

This band pumps out the hits from the '70s, '80s, '90s, and music of today. Come on out! Bet you'll come back for a Second Slice!
Thu Jun 04, 2026
6:00 pm - 10:00 pm
Brownwood Paddock Square®
2726 Brownwood Blvd, The Villages, FL 32163

The Edge Of Rock

A Villages homegrown rock band delivering thrilling, high-energy renditions of classic rock and crowd favorites.
Fri Jun 05, 2026
6:00 pm - 10:00 pm
Brownwood Paddock Square®
2726 Brownwood Blvd, The Villages, FL 32163

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 Jun 06, 2026
6:00 pm - 10:00 pm
Brownwood Paddock Square®
2726 Brownwood Blvd, The Villages, FL 32163

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.
Sun Jun 07, 2026
6:00 pm - 10:00 pm
Brownwood Paddock Square®
2726 Brownwood Blvd, The Villages, FL 32163

Blonde Ambition

Blonde Ambition is an international special event show band based out of Orlando, FL. American Top 40, pop, rock, Motown, '70s, '80s, '90s, Latin cross-over, and more!
Mon Jun 08, 2026
6:00 pm - 10:00 pm
Brownwood Paddock Square®
2726 Brownwood Blvd, The Villages, FL 32163

Hacksaw Hamlin

Hacksaw Hamlin is a dynamic and versatile four piece band that combines danceable elements of '70s rock, blues, and country.
Tue Jun 09, 2026
6:00 pm - 10:00 pm
Brownwood Paddock Square®
2726 Brownwood Blvd, The Villages, FL 32163

Jerico

Leaning to the southern side of rock, Jerico celebrates the sounds of the last 6 decades!
Wed Jun 10, 2026
6:00 pm - 10:00 pm
Brownwood Paddock Square®
2726 Brownwood Blvd, The Villages, FL 32163
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