This weekend, Friday through Sunday, Boston’s World Trade Center and the adjacent Seaport Hotel will be the scene for a lavish musical fundraising event that has become an annual institution over the past 15 years. It’s "Steppin’ Out," a benefit to raise money for the Dimock Community Health Center in Roxbury. "Steppin’ Out" starts Friday with a Young Professionals Kickoff Party featuring actress Victoria Rowell, but it spreads its wings Saturday with a black-tie Crystal Ball that offers 12 different venues under the Trade Center roof, with "re-creations" of such famed Boston clubs as the Jazz Workshop, Hi Hat, Storyville, and the Savoy. More than 25 acts will perform, including the Cab Calloway Orchestra, T.S. Monk Jr., Chuck Mangione, Charles Neville & Hilary Noble, Jerry "Iceman" Butler, David Gilmore, Andre Ward, Angela Bofill, La Timba Loca, Semenya McCord, Motown Express, Laszlo Gardony, and Patricia Smith. The weekend comes to a close Sunday morning with a Gospel Brunch featuring Freda Battle & the Temple Worshippers.

The line-up was put together by veteran local promoter Fred Taylor, who ran Boston’s legendary Jazz Workshop and has kept busy in recent years booking the Tanglewood Jazz Festival and shows at Scullers Jazz Club, among other concert events. Taylor’s involvement accounts in part for the jazz-oriented line-up, the historical re-creations of clubs-gone-by, and the inclusion of acts like the up-and-coming Cab Calloway Orchestra and the local Cuban music group La Timba Loca.

Led by Cab’s grandson C. Calloway Brooks, the Orchestra aims to carry on the traditional swinging sounds associated with Cab Calloway. Brooks has adopted the gruff voice and swank Cotton Club suit of his big-band-leading grandfather, whom he remembers he started watching and listening to when he was just five. "I loved to watch him rehearse. You can find what an artist intends to create at a rehearsal." Brooks met Duke Ellington when he was three, Louis Armstrong at nine. Dizzy Gillespie called every year to wish them a Merry Christmas. "I was surrounded by titanic musicians. Only when you look back can you see how special it was."

After graduating in 1980 from the New England Conservatory, Brooks performed with the Lionel Hampton and Duke Ellington Orchestras, Rufus Reid, and Cyrus Chestnut, among others, and released a CD of solo guitar. Content that he had established his own musical voice, he picked up Cab’s baton. "Granddad told me about these great charts he did that had never been recorded. A few years after he passed away in 1994, I decided it was time to perpetuate his legacy."

Under Brooks, the 13-piece CCO focuses on the golden era of the orchestra, the 1930s through 1950s, when Cab led bands that featured Dizzy Gillespie, saxman Ben Webster, and drummer Cozy Cole. Brooks has made the first recordings of some of Cab’s classic charts as well as a few surprise finds. "Generally, the music that was unrecorded is more sophisticated material." Still, he insists that there’s much more to be mined from even Calloway’s best-known material.

La Timba Loca, an 11-piece powerhouse who’ll play in Steppin’ Out’s "Western Front" room, also strive to shine new light on traditions that leader Gonzalo Grau first learned from his grandfather. "I learned the old salsa songs at home in Caracas with him, and that showed me the true essence of the style."

A 1995 graduate of Berklee, Grau scored parts for the salsa numbers in Osvaldo Golijov’s La Pasión segundo San Marcos, and he plays piano and percussion in the touring company. Despite the success of such traditional salsa musicians as Buena Vista Social Club in the last decade, Grau felt the genre was getting lost and needed a modern twist. He discovered that twist in timba, a hard-edge mix of salsa syncopations with street-filtered funk, jazz, hip-hop, and rock.

"Timba is the new salsa," he explains. "It’s a younger, more freestyle approach to salsa and dancing from Cuba, where it’s played by people like Isaac Delgado, Los Van Van, NG La Bamba, and Bamboleo. With older salsa, the performance was largely confined to the stage, the players separated from the audience. Timba breaks down that barrier. We can stretch out the story line of a song to really involve the audience and go crazy with it."

Steppin’ Out takes place this Friday through Sunday, November 8 through 10, at the World Trade Center, 164 Northern Avenue. Call (617) 442-8800.