Upcoming Shows

These days, you’ll find (and hear) Michael playing both solo and with His New Best Friends. AND Michael hosts a weekly trivia night. There’s a lot going on.

End-of-2024 Update: It was an amazing year with 45+ music gigs (solo, New Best Friends, etc.), 90+ trivia nights, and more than a few appearances by Krampus here in the holiday season. A few gigs are already on the horizon in the new year, and Michael and his pals will be recording some new material in early 2025. Sign up on his mailing list (in the panel above) to keep up to date on all events as they roll in.

Music & Trivia Dates

Thursday March 27th
Weekly Trivia @ El Vaquero Winery
This week’s theme: “Happy Birthday Ron Howard!” Game starts at 7:00pm.

Sunday March 30th
De Tierra Vineyards
Mission 3SE, 5th Ave, Carmel-By-The-Sea

Michael returns to his favorite Carmel winery. Playing solo from 3:00 to 5:00pm.

Thursday April 6th
Weekly Trivia @ El Vaquero Winery
This week’s theme: “I Want Candy.” Game starts at 7:00pm.

Saturday April 12th
Meder Street Barn (house concert), Santa Cruz

Michael & His New Best Friends (full band) play an early evening of all-original tunes – including some newly recorded songs – in this intimate local venue. Potluck at 2:30pm followed by music at 4:00pm concert. $25 donation at the door. Reserve your seats by going to mederstreetbarn.com.

Sunday May 25th
Damm Vineyards (and Pinnacles Brewing Company)
3028 Cienega Road, Hollister 

Michael Gaither and His New Best Friends (in trio mode) play from 12:30 to 3:30pm. No cover and no reservations required.

Saturday May 31st
Snazzy Productions @Kuumbwa Jazz Center
320-2 Cedar Street, Santa Cruz

A full evening of musical laughs as the duo Schoolcraft & Murray celebrate their new record. Michael opens the show with a short set of original tunes! Music at 7:00pm. Tickets available at snazzyproductions.com. 

Sunday June 1st
Woody & Arlo Guthrie Tribute Concert
Cambria Center for the Arts
1350 Main Street, Cambria, CA 93428

An afternoon of Central Coast and Santa Cruz artists celebrating the music of Woody and Arlo. Each artist performs three songs. Music from 2:00 to 4:00pm. Tickets are $25 in advance and available at my805tix.com.

Ongoing Trivia Nights

  • Trivia Thursdays at El Vaquero Winery, 2901 Freedom Blvd in Corralitos. One long game with four categories, including visual and audio rounds, and usually centered around a trivia theme for the evening. Wine to the three top-scoring teams. Game starts at 7:00pm. No reservations necessary.
  • TIP: Check Michael’s Instagram @michael_gaither on game each Thursday for hints about that evening’s theme and topics.

View Page