The week ahead at a glance

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 TUE Mountain Winery Overlook Lounge pre-show (5:00-7:45pm)  Simon & Dave

Main stage: Jackson Browne

9/10 WED private event (Campbell)  4:00-5:45pm

AND… Bibo’s NY Pizza (Willow Glen) 6:45-8:45pm (Simon solo)

9/11 THU Lamella Tavern (Willow Glen) 6:30-9:00pm (Simon solo)

9/12 FRI  Sheraton (Palo Alto) 3-5pm (Simon & Don)

9/13 SAT  Spin A Yarn Restaurant (Fremont) 7-10pm

(Simon & Don)

9/14 SUN Cloud City (Campbell Farmers Market) 

9-11am (Simon & Don)

AND… Satori Cellars (Gilroy) 1:30-4:30pm (Simon solo)

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) 9am-12pm (Simon & Don)

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

9/22 MON  Mountain Winery Overlook Lounge pre-show 5:00-7:45pm (Simon solo)

Main stage: Band of Horses / Iron & Wine

9/25 THU Lamella Tavern (Wilow Glen) 6:30-9:00pm (Simon solo)

9/26 FRI Sheraton Palo Alto 3-5pm

AND… Private event (school

fundraiser - Schaeffer) 7-9pm

9/27 SAT  Spin a Yarn (Fremont) 7-10pm (Simon & Don)

9/28 SUN Cloud City (Campbell Farmers Market) 9-11am (Simon & Don) 

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  (temp hold) Private event

10/4  SAT Verde Vineyards (Gilroy) 1-4pm (ME Duell & Simon) 

AND…  Venture CC (Los Gatos) 5:30-8:00pm (Simon & Don)

10/5 SUN Cloud City (Campbell Farmers Market) 9-11am (Simon solo) 

AND… Solis Winery 1-4

AND… Mountain Winery Overlook Lounge pre-show 5:30-7:45pm (Simon solo) 

Main stage: Rumours of Fleetwood Mac(Fleetwood Mac tribute)

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)

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 (San Carlos) 6-8pm (Simon solo)

10/16 THU  Lamella Tavern (Willow Glen) 6:30-9:00pm (Simon solo)

10/17 FRI Sheraton Palo Alto 3-5pm 

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)

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 solo

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

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)

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

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)

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 7-10pm (duo)

12/7 SUN Cloud City (Campbell Farmers Market) 

9am-12pm (Simon & Don) 

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

12/13 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)

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

12/31 WED (available)

* Last updated on 9/10/25