Will Dailey (pictured) may not have won in his vocalist, songwriter or video categories at this week’s Boston Music Awards, but he’s dominated that winner’s circle before, even as he remains one of this town’s most unheralded treasures. He’s a really adept guitar player as well and will air his engaging pop-rock tunes from his latest album, Golden Walker, in the Burren Backroom Series in Davis Square both Friday and Saturday. Rapper Cliff Notez opens and, yes, he just won a Boston Music Award for best new artist.

If you’re in the holiday spirit, tap the source with Darlene Love – the Phil Spector-era hitmaker whose “Christmas (Baby Please Come Home)” was an annual highlight on David Letterman’s late show – when Love comes to town at Medford’s Chevalier Theatre on Friday. The same night, the Cabot in Beverly turns to a dynamic jazz-blues combo in singer Catherine Russell and singer/guitarist John Pizzarelli for a tribute to Billie Holiday and Frank Sinatra.

Punk-rockers the Street Dogs – who also just grabbed a Boston Music Award – continue to ring bells at the Brighton Music Hall on Friday through Sunday with their 13th annual Wreck the Halls shows. And it looks like a great Friday night to catch Club d’elf dropping its experimental grooves at the Lizard Lounge with a dynamic spread of guests that includes saxophonist Dana Colley, guitarist Jeff Lockhart, turntable whiz Mister Rourke and keyboardist Amy Bellamy.

Saturday brings the maverick Ohio folk trio Caamp to Royale, soul vocal firebrand Patti LaBelle to Medford’s Chevalier Theatre, the Weepies (the folk-pop duo of Deb Talan and Steve Tannen) to the Cabot, and Nashville-based singer/pianist Jon McLaughlin to City Winery, dipping into a holiday repertoire on his This Time of Year Tour. For jazz enthusiasts, Saturday also offers the annual John Coltrane Memorial Concert at Northeastern’s Blackman Auditorium. This year’s program, “My Favorite Things,” honors sax masters Bill Pierce and Stan Strickland with a band featuring several additional saxophonists (including musical director Carl Atkins and event co-founder Leonard Brown) as well as pianist Laszlo Gardony, bassist John Lockwood and drummer Yoron Israel.

Speaking of sax spirituality, Sunday offers the summit of the weekend when winds guru Charles Lloyd teams with roots singer/songwriter Lucinda Williams and his all-star band the Marvels (including guitarist Bill Frisell) for an impressionistic Celebrity Series event at the Berklee Performance Center.