He might also perform “Limehouse Blues,” from “Cannonball Adderley Quintet in Chicago.” Like “Little Niles,” the Davis and Adderley albums were released in 1959, and Mr. Cobb, who appeared on both, has been revisiting them in recent years with Mr. Jackson playing parts originated by John Coltrane.

“He loves John Coltrane,” Mr. Cobb said. “He says John is the only guy he ever dreamt about. Since he knows that I played with John Coltrane, we do a lot of those tunes.”

Mr. Jackson, the festival’s artistic director, said he works to strike a balance as he interprets music associated with venerated artists like Coltrane. “The spirit is strong in those recordings,” he said. “It’s going to be coming through me. Hopefully, I can find a way of being me but still distilling the influence of my heroes.”

Rounding out the program on the main stage will be the trombonist Craig Harris and the singers Chico Alvarez, with the Palomonte Afro-Cuban Big Band, and Charenée Wade. A nearby pavilion will host lesser-known acts, among them the guitarist Slam Allen and the singer Stephanie Hancock, as well as the Dutchess County Community College Jazz Ensemble.

The festival is a relatively small affair, but it has attracted the attention of heavy hitters like George Wein, who founded the Newport Jazz Festival. Mr. Wein praised the founder of Jazz in the Valley, Greer Smith, for her knowledge and advocacy of jazz, adding that small events of quality play a part in the festival ecosystem, raising the profile of young musicians and giving a lift to the locales in which they are held.

“We encourage these things,” he said.

Ms. Smith pointed to the social and psychological benefits to the community, including the residents of the Rip Van Winkle housing project, which is perched on a hill above Waryas Park. While many of the housing project’s young residents had little awareness of jazz history before visiting the festival, she said, they discovered a shared cultural heritage, as part of the African diaspora, with distinguished artists onstage.

“That’s the whole point,” said Ms. Smith, the president of Transart and Cultural Services, a Kingston nonprofit that promotes art of African descent and is presenting the festival.