Lower Hutt-born Crayford and his band will also play his latest work in Wellington and Auckland before he travels to Australia later this month for the release of his latest jazz trio album Dark Light, which features Crayford, Ben Street and Dan Weiss playing tunes he composed in London early last year.
Crayford is also recording two albums of solo piano music in Spain and has a cinematic opera project he is writing and directing, with a teaser already shot in New York.
Crayford will be joined on his Biggish Band dates by Rick Cranson on drums, Rio Hemopo on bass, Daniel Ryland on guitar, Rachelle Eastwood on flute, Dan Yeabsley playing baritone, Terry Crayford on sousaphone, Bridget Kelly on bass clarinet, Lucien Johnson on tenor saxophone and Crayford himself on keyboards.
Crayford said he was eager to play his debut in Masterton after only ever passing through the town on a motorcycle.
"I've not been to Masterton to play before but I ride my motorbike through there often.
"I've been living and playing in Spain, Austria and New York and while it sounds like a kind of glamorous life, the reality is you've got to move a bit with music. I'm kind of a nomad."
He had first collaborated musically with Maxwell, when he played several years ago as a guest artist alongside Chris O'Connor on a TrinityRoots tour.
Biggish Band member Hemopo is also a founding member of the TrinityRoots group and band drummer Cranson also plays in Little Bushmen.
"There's connections here and, even though it's not a directly musical relationship with Warren, it's nice to be putting this together around his Masterton venue," he said.
"We're putting a lot of effort into it."
Crayford said he planned to continue developing his ensemble work and his musical connections in New Zealand.
"It's great to have had the time and opportunity during this trip to get these players together and put it in a setting in which I had always intended it be in. It's something I'm going to keep working through over the next few years."
He said his present live repertoire was influenced by his time in New York, when he visited Harlem to hear Guinean singer Natou Camara.
"It's a big book of music and a huge amount of work went into writing it, as always for a lot of instruments, and it's kind of afro-funky music you can listen to and music you can dance to as well. It's good high art fun."
Presale tickets are available for Jonathan Crayford's Biggish Band at King Street Live at $25 each from www.eventfinder.co.nz. Door sales also will be available and the music plays from about 8.30pm.