The week ahead at a glance

MAY

5/14 WED State Street Market (Los Altos) 6-8pm (Simon solo)

5/15 THU Lamella Tavern (Willow Glen) 7-10pm (Simon solo)

5/17 SAT Campbell Boogie (First Street Stage)  10am-12pm (Simon solo)

AND… Capitola Wine Bar “VDUBS in the Village” event (Capitola)  1-4pm (Simon solo) & 5:30-8:30pm  (Simon solo)

5/18 SUN Campbell Boogie (First Street Stage) 10am-12pm (Simon, Don, and A.J

AND…. Verde Vineyards (Gilroy) 1-4pm (Simon, Don, and Dave)

5/21 WED  private event  (Cupertino) 6:00-8:30pm.  (Simon solo)

5/22 THU 20 Twenty Cheese & Wine Bar (Willow Glen) 6:30-8:30pm (Simon solo)

5/23 FRI 

5/24 SAT Rootstock (Los Gatos) 7-10pm  (Simon & Don)

5/25 SUN Cloud City (Campbell Farmers Market) 9-11am (Simon & Don)

AND…  Byington Winery (Los Gatos) 1-4pm solo

5/28 WED Bibo’s Pizza

5/31 SAT private event (Tracy) 5-7pm

JUNE

6/1 SUN Cloud City (Campbell Farmers Market) 9-11am (Simon & Don)

6/4 WED hold (private event)

6/5 THU Lamella Tavern (Willow Glen) 7-10pm (Simon solo)

6/6 FRI Saki’s Spin A Yarn (Fremont) 7-10pm (Simon solo)

6/7 SAT (Campbell Car show 9am-12pm) Trio

AND second set 12:30-3:30pm (Simon solo)

AND… private party (Willow Glen) 6-8pm

6/8 SUN Cloud City (Campbell Farmers Market) 9-11am (Simon & Don)

AND… Testarossa Winery (Los Gatos) 11:30am-1:30pm 

6/11 WED Bibo’s Pizza

6/14 SAT Car Show @ Venture CC (Los Gatos) 9am-1pm (Simon & Dave)

6/15 SUN Cloud City (Campbell Farmers Market) 9-11am (Simon & Don) 

AND… Horse Thief Vineyard (Morgan Hill) 1-4pm (Simon solo)

6/17 TUE Santa Clara University.  2:30-4:00pm.  (Simon solo)

6/18 WED Bibo’s Pizza

6/21 SAT 

6/22 SUN Cloud City (Campbell Farmers Market) 9-11am (Simon & Don)

1:30-3:30pm Ainsley House garden - Tony Lindsay)

4:30-6:30pm private party (Ashby) (Simon and Don)

6/24 hold mw

6/25 WED Bibo’s Pizza

6/28 SAT Boardwalk Bowl (Santa Cruz) 5-8pm (Simon solo)

6/29 SUN Cloud City (Campbell Farmers Market) 9-11am (Simon & Don) 

AND… Horse Thief Vineyard (Morgan Hill) 1-4pm (Simon solo)

JULY

7/3 THU private party RQ (San Jose) 6-9pm

7/5 SAT Gilroy Farmers Market 10am-1pm.  (Solo show)

AND… Spin A Yarn Steakhouse (Fremont) 7-10pm (Simon solo)

7/6 SUN Cloud City (Campbell Farmers Market) 9-11am (Simon & Don)

AND… Solis Winery (Gilroy) 1-4pm (Simon solo)

7/13 SUN Cloud City (Campbell Farmers Market) 9-11am (Simon & Don)

7/19 SAT  L&M Vineyards (Gilroy) 5-8pm.  (Duo/trio tbd)

7/20 SUN Cloud City (Campbell Farmers Market) 9-11am (Simon & Don)

AND… Cinnabar Winery (Gilroy)  1-4pm.  (Simon solo)

7/23 WED Little Lou’s (Campbell)  6-9pm   (Simon, Don, and ___)

7/24 THU Houserockers at Almaden (Graystone Park)

7/26 SAT Boardwalk Bowl (Santa Cruz) 5-8pm (Simon solo)

7/27 SUN Cloud City (Campbell Farmers Market) 9-11am (Simon & Don)

7/30 WED State Street Market (Los Altos) 6-8pm (Simon solo)

7/31 THU Lamella Tavern (Willow Glen) 7-10pm (Simon solo)

AUG

8/1 FRI Mimosa’s (Willow Glen) 6-9pm (trio)

8/2 SAT Spin A Yarn Restaurant (Fremont) 7-10pm (Simon solo)

Hold mw

8/3 SUN Cloud City (Campbell Farmers Market) 9-11am (Simon & Don) 

AND… Verde Vineyards (Gilroy) 1-4pm (Simon and)

8/9 SAT hold mw

Private Event (SCCLPA) 8-10pm

8/10 SUN Cloud City (Campbell Farmers Market) 9-11am (Simon & Don) 

AND… Clos La Chance (San Martin) 1-4pm (Simon solo)

8/13 WED Crows Nest (Simon solo)

8/14 THU Lamella Tavern (Willow Glen) 7-10pm (Simon solo)

8/17 SUN Cloud City (Campbell Farmers Market) 9-11am (Simon & Don)

8/19 Hold mw

8/23 SAT Cinnabar Winery (Gilroy) 1:30-4:30pm (Simon solo)

8/24 SUN Cloud City (Campbell Farmers Market) 

9-11am (Simon & Don)

AND… Ainsley House “garden grooves” (Mary Ellen & Thom Duell w/ Simon Santiago) 1:30-3:30pm

8/28 hold mw

8/31 SUN Cloud City (Campbell Farmers Market) 9-11am (Simon & Don)

SEPT

9/7 SUN Cloud City (Campbell Farmers Market) 9-11am (Simon & Don)

9/13 SAT Spin A Yarn

9/14 SUN Cloud City (Campbell Farmers Market) 9-11am (Simon & Don)

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

9/20 SAT Relay For Life (San Jose) 5-7pm

9/21 SUN Cloud City (Campbell Farmers Market) 9-11am (Simon & Don)

9/26 FRI Private event (school

fundraiser - Schaeffer)

9/28 SUN Cloud City (Campbell Farmers Market) 9-11am (Simon & Don) Verde Vineyards 1-4pm

OCT

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

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 & Don)

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

10/18 SAT Spin A Yarn

10/19 SUN Cloud City (Campbell Farmers Market) 9-11am (Simon & Don)

AND… Verde Vineyards (Gilroy) 1-4pm  (duo)

10/22 hold mw

10/23 hold mw

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)

NOV

11/1 SAT Gilroy Farmers Market 10am-1pm (Simon solo)

11/2 SUN Cloud City (Campbell Farmers Market) 9-11am (Simon & Don)

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

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

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

11/29 SAT Solis 

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

DEC

12/7 SUN Cloud City (Campbell Farmers Market) 9-11am (Simon & Don) 

12/14 SUN Cloud City (Campbell Farmers Market) 9-11am (Simon & Don)

12/21 SUN Cloud City (Campbell Farmers Market) 9-11am (Simon & Don)

12/28 SUN Cloud City (Campbell Farmers Market) 9-11am (Simon & Don)

* Last updated on 5/10/25