The week ahead at a glance

OCT

10/10 FRI  Mountain Winery Overlook Lounge pre-show 5:00-7:45pm (Simon solo) Main stage: John Mulaney

(Simon & Paul Keller)

10/11 SAT Cinnabar Winery (Gilroy) Grape Stomp special event.  1-4pm (Simon solo)

AND… Tessora’s Wine Bar (Campbell)  7-9pm (Simon solo)

10/12 SUN Cloud City (Campbell Farmers Market) 9-11am (Simon solo)

AND… Clos La Chance (San Martin) 12-3pm (Solo show)

AND… The District (San Jose) 5:30-7:30pm (Simon, Don, and Dave)

10/15 WED State Street Market (Los Altos) 6-8pm (Simon solo) 

10/16 THU  El Jardin/Zazil (Santana Row) 6-9pm (Mary Ellen Duell & Simon)

10/17 FRI Sheraton Palo Alto 3-5pm (Simon & Don)

10/18 SAT  Campbell coffee shack 11am-2:30pm (Simon solo)

Private Event (Hapa’s, Los Gatos) 6-10pm (Simon solo)

10/19 SUN Campbell Oktoberfest (First St. stage) 10am-12pm (Simon & Don) AND… full band 12:30-2:30pm (w/ Simon, Don, Dave, and A.J.)

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… Spin A Yarn (Fremont) 8:30-10:30pm (Simon & Don)

10/25 SAT Lamella Tavern 7-10pm (Simon solo)

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)

AND… HR 7pm

11/2 SUN Cloud City (Campbell Farmers Market) 9am-12pm (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 (Simon solo)

11/8 SAT Verde Vineyards (Gilroy) 1-4pm (Simon & Dave)

AND…. Lamella Tavern (Willow Glen) 7-10pm (Simon solo)

11/9 SUN Cloud City (Campbell Farmers Market) 9am-12pm (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)

11/15 SAT Campbell Coffee Shack 11am-2:30pm (Simon solo)

11/16 SUN Cloud City (Campbell Farmers Market) 9am-12pm (Simon & Don)

11/17 MON Chaminade (Santa Cruz) 5:30-8:30pm (Simon solo)

11/18 TUE West Gate Villa (San Jose) 5-6pm (Simon solo)

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

AND… Spin A Yarn (7-10pm) duo

11/22 SAT Lamella Tavern (Willow Glen) 7-10pm (Simon solo)

11/23 SUN Cloud City (Campbell Farmers Market) 9am-12pm (Simon & Don)

(HOLD afternoon/sub at Solis)

11/25 TUE  Sam’s BBQ (San Jose)  6-9pm (Simon, Don, and Dave)

11/26 WED  414 California Ave (Palo Alto) 5-8pm  (Simon solo)

11/28 FRI  Sheraton Palo Alto 3-5pm (Simon & Don)

AND… Spin A Yarn 7-10pm  (duo)

11/29 SAT Solis Winery (Gilroy) 1-4pm (Simon solo)

11/30 SUN Cloud City (Campbell Farmers Market) 9am-12pm (Simon & Don)

DEC

12/3 WED  414 California Ave (Palo Alto) 5-8pm  (Simon solo)

12/6 SAT Morgan Hill Library (holiday & pop/rock mix)

2pm (Simon solo)

AND…. Spin A Yarn (Fremont) 7-10pm (Simon & Don)

12/7 SUN Cloud City (Campbell Farmers Market) 

9am-12pm (Simon & Don) 

12/10 WED  414 California Ave (Palo Alto) 5-8pm  (Simon solo)

12/11 THU Chaminade (Santa Cruz) 5:30-8:30pm (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) 9am-12pm (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)

12/20 SAT Spin A Yarn 7-10pm (solo/duo)

12/21 SUN Cloud City (Campbell Farmers Market) 9a-12pm (Simon & Don)

12/26 FRI  Auto Vino (San Carlos) 5-7pm.  (Simon & Don)

12/27 SAT Rootstock (Los Gatos) 7-10pm  Simon & Don

12/28 SUN Cloud City (Campbell Farmers Market) 9am-12pm (Simon & Don)

12/31 WED (available)

* Last updated on 9/14/25Tlm