The Black Watch, at 145 N. Santa Cruz Ave., is located in what used to be a Greyhound bus station. Until the early ’40s, behind that long bright green tile facade, buses would drive into what is now Mr. Pickle’s Sandwich Shop to pick up passengers—exiting at the other end. Very old-timers remember how, as children, they could catch buses here to get around town or head “over the hill” to the beach.
Jennifer Anzalone, a third generation Anzalone, tends bar at the “Watch,” offering a warm welcome to those who enter.
(Los Gatos Library archives / courtesy of librarian Henry Bankhead)
The full bar is known for its Kamikaze special. Longtime bartender Robert Killion is an ordained minister and can perform marriage ceremonies.
The Black Watch has occupied this space since March 14, 1959, when Anthony “Tony” Anzalone Sr. and a Scottish co-owner opened it.
Hence the name “Black Watch,” which originally is a famous Scottish military regiment known for bravery (and their distinctive dark plaid tartans).
All in the family
The Black Watch has been an Anzalone family business since Sr. opened it. I wandered into the Watch on a quiet weekday afternoon.
Jennifer Anzalone, Tony’s granddaughter, was at the other end of the bar taking care of the local late afternoon crowd.
I sat at the bar next to two construction workers, off for the day, talking about anything but work.
In the early days, with Anzalone Sr. behind the bar, local WWII survivors, better known as “grumpy old men,” frequented the Watch.
Most weekdays, Jennifer’s uncle Brad opens the Watch up at 11am. If you would like a bit more local history, drop by.
These days there may be a few “grumpy old men” at the Watch.
However, it is mostly a mixed crowd and a great place for a drink before a movie down the avenue.
Before the Watch
The Black Watch is now the oldest bar in Los Gatos, and a favorite watering hole for locals and tourists. Tourists go in for tips on what to do while in Los Gatos. Locals enjoy the quiet, cool interior and friendly atmosphere. Some find it’s a great spot to wait out the beach traffic and to catch up on local news.
“They really know how to take care of us locals,” said Jim Blackburn, who amongst other things builds cajon drums.
Learn how the Pet Rock was born in one of these booths, and made a local a millionaire.
Black Watch co-owners Steve and brother Brad Anzalone survived the big quake. And they were closed for almost a year during the Covid-19 pandemic. But the bar has soldiered on.
