The week ahead at a glance

JULY

7/2 WED Bibo’s Pizza (Willow Glen) 6:30-8:30pm

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

7/4 FRI  Auto Vino (San Carlos) 5-7pm (Simon & Don)

7/5 SAT Gilroy Market Off First Street.  Debut!  40+ Makers, produce, flowers, local honey, and fresh bread.  10am-1pm.  (Solo show)

AND… Spin A Yarn Steakhouse (Fremont) 7-10pm (Simon & Don)  First duo show here!

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

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

7/10 THU Tessora’s Wine Bar (Campbell) 8-10pm (Simon solo)

7/12 SAT Satori Cellars (Gilroy) 1-4pm  (Simon solo)

AND… Rootstock Wine Bar (Los Gatos) 7-10pm (Simon solo)

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

AND… Byington Winery (Los Gatos) 1:30-4:30pm (Simon solo)

7/18 FRI Los Gatos Coffee Roasting Company (7-10pm) quartet w/ Simon, Don, Dave, and A.J.

7/19 SAT  L&M Vineyards (Gilroy) 5-8pm.  (Simon, Don, and Dave)

NEW VENUE!!!

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 Dave)

7/24 THU Houserockers at Almaden (Graystone Park) 6pm

AND… Tessora’s Wine Bar (Campbell) 8:30-10:30pm (Simon & Don)

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 Testarossa Winery @ Bistro 107.  (Los Gatos) 6-8pm (Simon solo)

AUG

8/1 FRI Mimosa’s (Willow Glen) 6-9pm (Simon, Don, and Dave)

8/2 SAT Mountain Winery (Overlook Lounge pre-show)

Main stage = Rick Springfield w/ John Waite, Wang Chung, and Paul Young)

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

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

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

8/6 WED 414 Cal Ave (Palo Alto) 5:30-8:30pm.  

NEW VENUE!!!

8/9 SAT  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 (Santa Cruz) 6-9pm (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 TUE Mountain Winery (Overlook Lounge pre-show)  main act = Blues Traveler w/ Gin Blossoms and Spin Doctors 

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

8/27 WED Sam’s BBQ (San Jose) 6-9pm   

8/28 THU Mountain Winery (Overlook Lounge pre-show) Main act = ZZ Top w/ Night Ranger

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

SEPT

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)

9/13 SAT 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)

9/20 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) 

AND… Verde Vineyards (Gilroy) 1-4pm

OCT

10/2 THU Private Event (Manteca)

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 Mountain Winery (Overlook Lounge pre-show) Main act = Daryl Hall (Hall & Oates) w/ Glenn Tilbrook (Squeeze)

10/23 Mountain Winery (Overlook Lounge pre-show) Main Act = Garbage w/ Starcrawler

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 Market Off First Street.  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 Winery (Gilroy) 1-4pm

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 7/1/25