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Entertainment

If you love live entertainment, you are in for a treat. As you stroll down Atlantic Avenue in Downtown Delray, the music spills into the streets. From classic rock to cool island reggae, there is a venue suited for everyone! We don't believe that entertainment is something that must be scheduled, we believe in making it happen on a daily basis. Nothing showing up on a local events calendar? Take a peek at what some of our merchants have going on; not to mention the exceptional events that are constantly drawing crowds at Old School Square or the Arts Garage. Seven nights per week, Downtown Delray is just what you want.

Old School Square

Classic Albums Live: Beatles, Sgt. Peppe

Sat
Sat, 12/28/2019
8:00pm - 10:00pm
Old School Square Pavilion

CLASSIC ALBUMS LIVE takes the world’s greatest musicians to faithfully recreate albums exactly the way they were recorded.

Old School Square

Free Friday Concerts – Higher Ground

Fri
Fri, 12/20/2019
7:30pm
Old School Square Pavilion

Higher Ground has one of the most diverse song lists of any cover band.

Delray Hideaway

Pool Tournament Mondays

Mon
Thu, 09/13/2018 to Sat, 12/31/2022
8:00pm - 1:00am

Every Monday with enough participants our lovely Lauren will host a single elimination pool tournament. Win prizes $$$

Delray Hideaway

Trivia Thursdays

Thur
Thu, 02/21/2019 to Mon, 02/21/2022
8:30pm - 10:30pm

Show off your big brain and win, get a group of friends together and come up with a clever team name, compete against other teams and...

Cloud 9 Adventures

Closer to the Sun

Thu, 12/05/2019 to Mon, 12/09/2019
Puerto Aventuras, Mexico

Leave your cares behind for four nights of music, all-inclusive amenities, and tons of extras with Slightly Stoopid and friends.

Old School Square

Free Friday Concerts – JM and The Sweets

Fri
Fri, 12/06/2019
7:30pm - 10:00pm
Old School Square Pavlion

Dallas Texas born/ Palm Beach Florida based singer/songwriter whose brand of Soul music encompasses a wide range of influences

Old School Square

Free Friday Concerts – Valerie Tyson Ban

Fri
Fri, 09/27/2019 to Fri, 12/27/2019
7:30pm - 10:00pm
Old School Square Pavilion

Valerie Tyson Band is a soulful and electrifying band that perform classic and modern music.

Delray Hideaway

Beer & Bingo Tuesdays

Tue
Thu, 02/21/2019 to Mon, 02/21/2022
7:00pm - 9:00pm

Free to play, prizes given out for every round...the most fun you can have on a Tuesday!

Delray Hideaway

Karaoke Fridays

Fri
Thu, 02/21/2019 to Mon, 02/21/2022
8:55pm - 1:00am

The most fun weekly singing event on the Ave! Participate or just watch and enjoy the show

Cloud 9 Adventures

Strings & Sol

Thu, 12/12/2019 to Mon, 12/16/2019
Puerto Morelos, MX

Join this tropical bluegrass vacation with a main stage on the beach, all-inclusive amenities, and a concert experience unlike any other...

Old School Square

Free Friday Concerts – The Clique

Fri
Fri, 12/13/2019
7:30pm - 10:00pm
Old School Square Pavilion

A dynamic new band…playing the hits from every genre…keeping the party moving!

Old School Square

4th Annual Carols by Candlelight

Sat
Sat, 12/07/2019
7:30pm - 10:00pm
Old School Square Pavilion

Gloria Gaynor with special guest performances by Mary Gaines Bernard (sister of Donna Summer) and the Holiday Voices.

Delray Hideaway

Poker Night!

Wed
Thu, 02/21/2019 to Mon, 02/21/2022
7:30pm - 10:30pm

No limit Texas Hold ‘em every Wednesday. Prizes to winners nightly, build your score every week for a chance to win the grand prize!

Delray Hideaway

Industry Night

Sun
Thu, 02/21/2019 to Mon, 02/21/2022
11:00pm - 2:00am

Where the locals go after work on Sunday, free pool and a good time. Industry workers enjoy 50% off with proof of employment after 11pm...

Cloud 9 Adventures

Jam Cruise 18

Tue, 01/07/2020 to Sun, 01/12/2020
Miami, FL • Bahamas • Costa Maya

Jam Cruise features a fully stacked lineup of artists performing nearly around-the-clock on multiple stages, while cruising the...