It’s a weekend bookended by far-ranging vocal stylists, with adventurous instrumentalists in the middle that span prog, avant-jazz and jam worlds. Friday kicks off with the still-spry-at-91 singer Tony Bennett at the Opera House, Afro-pop dynamo Angelique Kidjo (who just released her bold version of Talking Heads’ Remain in Light album) at Sanders Theatre, and the harmonies of locally bred bluegrass-folk combo Della Mae at the Sinclair with snappy peers Barnstar!

Cambridge’s cozy Lily Pad in Inman Square goes big for two nights this weekend. First, orchestral New York prog-rockers Edensong take over the space on Friday with the Ben Levin Group, led by the guitarist for Bent Knee. Then Saturday offers an especially rare treat for avant-garde diehards when Bay Area guitar hero Henry Kaiser makes his first appearance in decades with Plane Crash, a trio with upright bassist Damon Smith and drummer Weasel Walter that will be joined at the Lily Pad by drummer Ra-Kalam Bob Moses and LA multi-reeds player Vinnie Golia. Kaiser’s known for other collaborations with Wadada Leo Smith, Fred Frith and Derek Bailey as well as an album where he tackled the Grateful Dead’s “Dark Star/The Other One.” Which brings us to another Saturday pick at Somerville’s Thunder Road: the local debut of Ghost Light (pictured), a buzzed-about new jamband that boasts Joe Russo’s Almost Dead guitarist/singer Tom Hamilton, his American Babies guitar bandmate Raina Mullen, classically trained keyboardist Holly Bowling (known for her solo piano recreations of Dead and Phish jams), bassist Steve Lyons and Dopapod drummer Scott Zwang. Ghost Light‘s been developing originals in addition to covers on tour. And Saturday brings jiving, resolute Southern rock mavericks Rainbow Kitten Surprise to Royale.

Saskatchewan singer/songwriter Colter Wall, who graces the Sinclair on Sunday, possesses a striking, classic country voice that he brings to his autobiographical country-folk Americana. The same night offers very different stylists in Rodriguez, the Detroit-born singer/songwriter who found fame in South Africa documented in the film “Searching for Sugar Man,” at the Wilbur, while House of Blues rolls back to ’80s nostalgia with the suave, sassy English hitmaker Rick Astley.