The week ahead at a glance

7/26 SAT  Mountain Winery  Patio/wine tasting (2-4pm), and Overlook Lounge 5:30-7:30pm Main Stage:  Smokey Robinson

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  Mountain Winery Overlook Lounge pre-show: Lynyrd Skynyrd 

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

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

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

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

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

NEW VENUE!!!

8/8 FRI  Mountain Winery Overlook Lounge pre-show: Andy Grammer

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)

8/12  TUE  Mountain Winery Overlook Lounge pre-show: 

Buddy Guy

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

8/15 FRI Spin A Yarn restaurant (Fremont) 7-10pm (Simon & Don)

8/16 SAT private party (Hayward) 1:30-3:30pm (Simon solo)

AND…  Mountain Winery Overlook Lounge pre-show: Diana Ross

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

AND… Mountain Winery Overlook Lounge pre-show: Beach Boys

8/19 TUE Mountain Winery (Overlook Lounge pre-show)  Blues Traveler w/ Gin Blossoms and Spin Doctors 

8/20 WED Bibo’s NY Pizza (Willow Glen) 6:30-8:30pm (Simon solo)

8/21 THU  Mountain Winery Overlook Lounge pre-show: Trampled By Turtles & Shakey Graves

8/22 FRI  Mountain Winery Overlook Lounge pre-show: 

Air Supply

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

8/26 TUE   Mountain Winery Overlook Lounge pre-show: 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) Main act = 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: 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)

9/6 SAT private party (Willow Glen) 6-8pm (Simon, Don, Dave, Paul)

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

9/10 WED (hold fo Campbell Chamber)

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)

9/19 FRI  Auto Vino (San Carlos) 5-7pm.  (Simon & Don)

9/20 SAT 

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 

10/10 FRI  Devil’s Canyon Brewery (San Carlos) 6:30-9:00pm (Simon solo)

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  Private Event LG (*Spin A Yarn)

10/19 SUN Campbell Oktoberfest (First St. stage) 10am-12pm (Simon, Don, and A.J.)

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

10/22 WED  Mountain Winery (Overlook Lounge pre-show) Main act = Daryl Hall (Hall & Oates) w/ Glenn Tilbrook (Squeeze)

10/23 THU  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)

10/31 FRI  Auto Vino (San Carlos) 5-7pm.  (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)

11/9 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)

11/28 FRI  Auto Vino (San Carlos) 5-7pm.  (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)

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

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

* Last updated on 7/22/25