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Welcome to Tricky Entertainment
"Love My City"

Tricky Entertainment is a Washington, DC based curator of live music and entertainment events. Through our company, we provide thousands of patrons with memorable experiences that include national and local artists. Our upscale events always leave our patrons with great anticipation for the next Tricky Entertainment experience.




8th Annual For The Cool In You Wine & Music Festival
Tickets Available Now!

Saturday, May 18 - Sunday, May 19, 2024

Charles County Fairgrounds - 8440 Fairground Rd. La Plata, MD 20646

For The Cool In You Wine & Music Festival 2024
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UPCOMING EVENT

8th Annual For The Cool In You Wine & Music Festival

Hosted by WPGC's Guy Lambert | Music by DJ Shablast

18
May 2024

Day 1: Kenny Lattimore

Sirius Company, Black Alley, and Frank McComb
Charles County Fairgrounds 12PM - Until Dark
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On Sale Now

19
May 2024

Day 2: Big Daddy Kane

Northeast Groover, Push Play, and Kevin Ross
Charles County Fairgrounds 12PM - Until Dark
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On Sale Now

18-19
May 2024

2-Day Festival Tickets

Charles County Fairgrounds 12PM - Until Dark
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On Sale Now

What people are saying about our events

"Summer Breeze was EPIC! It was way more than a party. It was classy and the way the crowd was managed by the Tricky, Inc. staff was OUTSTANDING! Truly the BEST party of the year. Thanks for loving your city."

Vanessa C.

"Had a great time! This is my second Tricky Entertainment event [All Black Extravaganza] and I had a BLAST!!! I will definitely be at the next event."

Diondra D.

"This is my first time coming to a Tricky Event and I was very impressed. Excellent party. My wife and I had a great time! All positive. It was very well put together. Thank you for Summer Breeze."

Aaron S.

EVENT VIDEOS

Watch promo videos and highlights from our events.

Tricky Entertainment's 2023 Summer Breeze
Featuring Tamar, Rare Essence, Top 5, and Black Alley

Tricky Entertainment Celebrates 20 Years at the All Black Extravaganza 2023
Featuring Keyshia Cole/Joe

SummerBreeze 2017 Nationals Park
Featuring Tamia

ANNUAL EVENTS

Events you don't want to miss!

All Black Extravaganza
All Black Extravaganza

Our annual All Black Extravaganza is a chance for stylish and sophisticated ladies and gents to paint the town in ALL BLACK. This event is held at the finest venues, set apart by the best live performances and entertainment making it a night to remember.

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For The Cool In You Wine and Music Festival
4 The Cool In You Wine & Music Festival

4 The Cool In You Wine & Music Festival is Tricky's annual wine and music festival offers amazing food and cigar vendors, local wineries, merchandise and much more! This 2-day event also features five genres of music by local and national artists!

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Summer Breeze
Summer Breeze

Summer Breeze "Linen & Dresses" is one of the most coveted and highly anticipated events of the summer. This outdoor musical experience attracts people from the ATL to L.A. The perfect combination of live performances by national and local artists.

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