ALL UPCOMING GIGS
All upcoming gigs…
8/19 TUE Mountain Winery (Overlook Lounge pre-show) 5:00-7:45pm (Simon & A.J.)
Main stage: Blues Traveler w/ Gin Blossoms and Spin Doctors
8/20 WED Bibo’s NY Pizza (Willow Glen) 6:30-8:30pm (Simon solo)
8/24 FRI Mountain Winery (Overlook Lounge pre-show) 5:00-7:45pm (Simon solo)
Main stage: Air Supply
8/23 SAT Cinnabar Winery (Sip & Shop event) (Gilroy) 1-4pm (Simon solo)
AND… Los Gatos Coffee Roasting Co (Los Gatos) 7-9pm (Simon, Don, and A.J.)
8/24 SUN Cloud City (Campbell Farmers Market)
9-11am (Simon & Don)
AND… Overlook Lounge at Mountain Winery pre-show (5:00-7:45pm) Simon solo
Main stage: Gipsy Kings
8/26 TUE Mountain Winery Overlook Lounge pre-show 5:00-7:45pm (Simon solo)
Main stage: Michael Franti
8/27 WED Sam’s BBQ (San Jose) 6-9pm (Simon, Don, and A.J.)
8/28 THU Mountain Winery (Overlook Lounge pre-show) 5:00-7:45 (Simon & Dave)
Main stage: ZZ Top w/ Night Ranger
8/29 FRI Auto Vino (San Carlos) 5-7pm. (Simon & Don)
8/30 SAT Mountain Winery (Overlook Lounge pre-show) 5:00-7:45pm.
Main Stage: LOST 80’s
8/31 SUN Cloud City (Campbell Farmers Market) 9-11am (Simon & Don)
SEPT
9/2 TUE Chaminade Resort & Spa (Santa Cruz) 5:30-8:30pm (Simon solo)
9/3 WED Mountain Winery Overlook Lounge pre-show 5:00-7:45pm (Simon & Dave)
Main stage: Post Modern Jukebox
9/5 FRI Davenport Roadhouse
6-9pm (Simon solo)
9/6 SAT private party (Willow Glen) 6-8pm (Simon, Don, Dave, Paul)
9/7 SUN Cloud City (Campbell Farmers Market) 9-11am (Simon & Don)
and… Mountain Winery
(Overlook Lounge pre-show) 5:00-7:45pm (Simon & Dave)
Main stage: Chicago
9/9 WED Mountain Winery Overlook Lounge pre-show (5:00-7:45pm) Simon & Dave
Main stage: Jackson Browne
…. **** (Bibo’s) NY Pizza (Willow Glen) 6:30-8:30pm (Simon solo)
9/11 THU Lamella Tavern (Willow Glen) 7-10pm (Simon solo)
9/12 FRI Sheraton (Palo Alto) 3-5pm (Simon & Don)
9/13 SAT (hold Napa party)
AND… Spin A Yarn Restaurant (Fremont) 7-10pm
9/14 SUN Cloud City (Campbell Farmers Market)
9-11am (Simon & Don)
AND… Satori Cellars (Gilroy) 1:30-4:30pm (Simon solo)
9/16 TUE Mountain Winery Overlook Lounge pre-show (5:00-7:45pm) Simon solo
Main stage: 38 special
9/17 WED Bibo’s NY Pizza (Willow Glen) 6:30-8:30pm (Simon solo)
9/18 THU Campbell Winewalk 6-9pm (Simon, Don, and Dave)
9/19 FRI Auto Vino (San Carlos) 5-7pm. (Simon & Don)
9/20 SAT Cinnabar Winery (Gilroy) 1-4pm (Simon solo)
AND… L&M Vineyard (Gilroy) 5:30-8:30pm (Simon & Don)
9/21 SUN Cloud City (Campbell Farmers Market) 9-11am (Simon & Don)
9/22 MON Mountain Winery Overlook Lounge pre-show 5:00-7:45pm (Simon solo)
Main stage: Band of Horses / Iron & Wine
9/24 WED Mountain Winery Overlook Lounge pre-show (5:00-7:45pm) Simon solo
Main stage: UB40
9/25 THU Lamella Tavern (Wilow Glen) 7-10pm (Simon solo)
9/26 FRI Sheraton Palo Alto 3-5pm
AND… Private event (school
fundraiser - Schaeffer) 7-9pm
9/27 SAT Mountain Winery Overlook Lounge pre-show 5:00-7:45pm (Simon solo)
Main stage: Common Kings
9/28 SUN Cloud City (Campbell Farmers Market) 9-11am (Simon & Don)
AND… *** Verde Vineyards (Gilroy) 1-4pm
AND… Mountain Winery Overlook Lounge pre-show (5:00-7:45pm) Simon solo w/ special guest: Jackie Chavez
Main stage: America
OCT
10/2 THU Private Event (Manteca) 11am-3pm
AND… El Jardin/Zazil (Santana Row) 6-9pm (ME Duell & Simon)
10/3 FRI Private event: Venture CC (Los Gatos) 4-8pm
10/4 SAT Verde Vineyards (Gilroy) 1-4pm (ME Duell & Simon)
AND… Venture CC (Los Gatos) 5:30-8:00pm
10/5 SUN Cloud City (Campbell Farmers Market) 9-11am (Simon solo)
AND… Solis Winery 1-4
AND… Mountain Winery Overlook Lounge pre-show 5:00-7:45pm (Simon solo)
Main stage: Rumours of Fleetwood Mac(Fleetwood Mac tribute)
10/9 THU Mountain Winery Overlook Lounge pre-show 5:00-7:45pm (Simon solo) Main stage: Marshal Tucker
10/10 FRI Mountain Winery Overlook Lounge pre-show 5:00-7:45pm (Simon solo) Main stage: John Mulaney
(Simon & Paul)
10/11 SAT Cinnabar Winery (Gilroy) Grape Stomp special event. 1-4pm (Simon solo)
*** (Hold for Spinayarn)
10/12 SUN Cloud City (Campbell Farmers Market) 9-11am (Simon solo)
AND… Clos La Chance (San Martin) 12-3pm (Solo show)
10/15 WED State Street Market (San Carlos) 6-8pm (Simon solo)
10/16 THU Lamella Tavern (Willow Glen) 7-10pm (Simon solo)
10/17 FRI Sheraton Palo Alto 3-5pm
*** (hold for Spinayarn)
10/18 SAT Private Event LG
10/19 SUN Campbell Oktoberfest (First St. stage) 10am-12pm (Simon, Don, and A.J.)
AND… Verde Vineyards (Gilroy) 1-4pm (Simon, Don & Dave)
10/22 WED Mountain Winery (Overlook Lounge pre-show) 5:00-7:45pm (Simon & Paul)
Main act = Daryl Hall (w/ opener Glenn Tilbrook)
10/23 THU Mountain Winery (Overlook Lounge pre-show) 5:00-7:45 (Simon solo)
Main Act = Garbage w/ Starcrawler
10/24 FRI Auto Vino (San Carlos) 5-7pm. (Simon & Don)
AND… hold SAA
10/25 SAT Lamella Tavern 7-10pm
10/26 SUN Cloud City (Campbell Farmers Market) 9-11am (Simon & Don)
AND… Satori Cellars (Gilroy) 1:30-4:30pm (Simon solo)
10/29 WED Crows Nest (Santa Cruz) 7-10pm (Simon solo)
10/30 THU Testarossa Winery (Los Gatos) 6-8pm (Simon solo)
10/31 FRI Sheraton Palo Alto 3-5pm (Simon & Don)
NOV
11/1 SAT Gilroy Market Off First Street. 10am-1pm (Simon solo)
11/2 SUN Cloud City (Campbell Farmers Market) 9-11am (Simon & Don)
11/5 WED 414 California Ave (Palo Alto) 5-8pm (Simon solo)
11/7 FRI Devil’s Canyon Brewery (San Carlos) 6-9pm solo
11/8 SAT Lamella Tavern (Willow Glen) Simon solo
11/9 SUN Cloud City (Campbell Farmers Market) 9-11am (Simon & Don)
11/12 WED 414 California Ave (Palo Alto) 5-8pm (Simon solo)
11/14 FRI Auto Vino (San Carlos) 5-7pm (Simon & Don)
11/16 SUN Cloud City (Campbell Farmers Market) 9-11am (Simon & Don)
11/19 WED 414 California Ave (Palo Alto) 5-8pm (Simon solo)
11/20 THU Testarossa Winery (Los Gatos) 6-8pm (Simon solo)
11/21 FRI Sheraton Palo Alto (3-5pm) Simon & Don
11/22 SAT Lamella Tavern (Willow Glen) 7-10pm (Simon solo)
11/23 SUN Cloud City (Campbell Farmers Market) 9-11am (Simon & Don)
11/26 WED 414 California Ave (Palo Alto) 5-8pm (Simon solo)
11/28 FRI Sheraton Palo Alto 3-5pm (Simon & Don)
11/29 SAT Solis Winery (Gilroy) 1-4pm (Simon solo)
11/30 SUN Cloud City (Campbell Farmers Market) 9-11am (Simon & Don)
DEC
12/3 WED 414 California Ave (Palo Alto) 5-8pm (Simon solo)
12/7 SUN Cloud City (Campbell Farmers Market)
9-11am (Simon & Don)
12/10 WED 414 California Ave (Palo Alto) 5-8pm (Simon solo)
12/13 SAT DeAnza holiday party (Santa Cruz) 5:30-8:00pm (Simon, Don, and Dave)
12/14 SUN Cloud City (Campbell Farmers Market) 9-11am (Simon & Don)
12/17 WED 414 California Ave (Palo Alto) 5-8pm (Simon solo)
12/18 THU Testarossa Winery (Los Gatos) 6-8pm (Simon solo)
12/21 SUN Cloud City (Campbell Farmers Market) 9-11am (Simon & Don)
12/26 FRI Auto Vino (San Carlos) 5-7pm. (Simon & Don)
12/28 SUN Cloud City (Campbell Farmers Market) 9-11am (Simon & Don)
12/31 WED (available)
* Last updated on 8/14/25d