Top

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. We are invested in our community and give back by speaking to young people and hosting turkey, food, toy, and clothing drives. After each "4 The Cool In You" Wine and Music Festival, a monetary contribution is made to different non-profit organizations. We also donate tickets to non-profit organizations that provide services to men and women in our local area.




Upcoming Event

10th Annual Wine and Music Festival June 13, 2026

10th Annual 2026 Tricky Wine Fest flyer
BUY TICKETS

PAST EVENTS

Bahama Breeze Music Festival

Bahama Breeze Music Fest flyer

9th Annual Wine and Music Festival

Tamia 2025 Tricky Wine Fest flyer

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.

Learn More
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!

Learn More
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.

Learn More
Love My City logo

Copyright 2024 © TRICKY ENTERTAINMENT, INC.