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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.

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.

Cloud 9 Adventures

Holy Ship! Wrecked

Wed, 01/22/2020 to Sun, 01/26/2020
Punta Cana, Dominican Republic

The premier electronic dance music cruise takes to the shores for an epic all-inclusive resort adventure. Lineup coming in June!

Cloud 9 Adventures

The Avett Brothers At The Beach

Thu, 02/27/2020 to Mon, 03/02/2020
Punta Cana, Dominican Republic

The third edition of The Avett Brothers At The Beach is headed to the DR for four nights of music in paradise.

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...

Cloud 9 Adventures

Wilco's Sky Blue Sky

Sat, 01/18/2020 to Wed, 01/22/2020
Riviera Maya, Mexico

A brand new destination vacation featuring 3 shows by Wilco plus a talented group of artists. On Sale Now!

Live Music Nights

Wed
Sat
Tue, 05/08/2018 to Tue, 12/31/2019
6:00pm - 10:00pm
104 NE 2nd Avenue - Pineapple Grove

Each Wednesday Night 6-9pm & Saturday Night 7-10pm
we feature various live music artists. From Blues to Gypsy Guitar. Always...

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...

Cloud 9 Adventures

Brandi Carlile Girls Just Wanna Weekend

Wed, 01/29/2020 to Sun, 02/02/2020
Riviera Maya, Mexico

An inspiring event featuring 3 shows by Brandi Carlile & an all female-fronted lineup performing in Mexico on the coast of the...

Festival Management Group

21st Annual South Florida Garlic Fest

Sat
Sun
Sat, 02/08/2020 to Sun, 02/09/2020
11:00am - 11:00pm
John Prince Park, Lake Worth, FL

The "Best Stinkin’ Party in South Florida" returns for 21 years of garlicky goodness!