Wynah Krew Entertainment was conceived in the summer of 1995 in Beltsville, Maryland, when a group of friends, known back then as the "Wynah Krew Boyz" hosted a low-key backyard get-together for family and friends. The get-together promised plenty of good food, music, and company, to one and all. Attendees tipically brought a beverage of their choice to share amounst friends. After several years of repeat performances, the get-together evolved into an annual tradition of socializing, on the weekend before Washington, DC Caribbean Carnival. Word eventually spreadthroughout the Metropolitan DC Caribbean community, of the the enjoyable event, and the practically free backyard "lime" grew into an eagerly anticipated event called "De Cookout". After five successful years of De Cookout, interest and attendance swelled. By the summer of 2003, De Cookout attracted approximately 2000 folks in search of a good time. The event's increased popularity overwhelmed the backyard in which it was conceived. It was time for a change.

In late 2003, the Wynah Krew Boyz established Wynah Krew Entertainment (WKE). De Cookout became a highly organized function, hosted at venues capable of accomodating all revelers seeking a good time. It was also change to an all-inclusive event. WKE goal is to provide the most entertaining "all-inclusive" party on the weekend prior to Washington DC's Caribbean Carnival. Over the years, the event has attracted several sponsorship from the likes of Heineken, Courvoisier, CaribUnited LLC, and Zanzibar On The Waterfront Nightclub.

In 2004 and 2005, the all-inclusive event, still affectionately known as De Cookout, was hosted at an estate in Boyds, Maryland. In 2006, WKE formed a partnership with Lake Arbor Country Club in Mitchellville, Maryland, and the event was hosted there for the first time in 2007. The event's time was also changed to 3pm to 12 midnight, and became The Official 'All-Inclusive' Day Fete.

In addition to De Cookout, Wynah Krew Entertainment, together with CaribUnited, LLC. hosts a "Family Picnic & Sports Day" as a way of giving back to the caribbean community, and fostering fellowship. This event encourages families with children to participate in various organized sports and activities. Wynah Krew Entertainment provides all food, gifts, and games, as well as officiates the sports and activities.

Wynah Krew Entertainment's 2008 All-inclusive Cookout event will take place on June 21, 2008, at the Lake Arbor Country Club in Mitchellville, Maryland.