Quick Take
San Francisco has lots of themed walking tours. Monterey has a few as well. Why not Santa Cruz? At least, that's the thinking of local artist and product designer Matt O'Leary, who is putting together a business offering walking tours of downtown Santa Cruz, maybe to expand to great surf spots and the UCSC campus.
Every city, every neighborhood, every street has a story. And, perhaps in some more neighborly, pre-internet, pre-digital-nomad world, most locals knew the stories of their hometowns and ’hoods.
But these days, when it’s just too easy to find yourself isolated and anonymous, even in a place where you’ve lived for years, cities need more storytellers to connect people with the stories that make up that ever-shifting, always hard-to-grasp thing we call “community.”
Into that space steps Matt O’Leary, whose latest venture, Walk Santa Cruz, aspires to create a series of informative walking tours in and around Santa Cruz, where he grew up and still lives.
San Francisco, unsurprisingly, has many guided walking tours. And, when O’Leary spent a couple of years living on the Monterey Peninsula, he was impressed by the tours offered there. And that led to a question:
Why not Santa Cruz?
O’Leary, 59, has already been leading tours, on an informal basis for friends, for years. “I worked over the hill for 10 years,” he said, “I commuted a lot and so a lot of people [over there] would say, ‘Oh, you live in Santa Cruz. Wow, it’s so mysterious and cool there.’ So I invited them to come over and I would show them around.”
Now, he is turning his casual invitations into a business offering a number of tours — the campus of UC Santa Cruz, the local state parks, and surf spots on the Westside and Eastside. But he’s launching with a tour of downtown Santa Cruz, including the Mission Hill district, that area around Holy Cross Church that is one of the most overlooked and underrated spots in downtown.
He said he is tailoring the tour to appeal to anyone who wants to learn more about the history and culture of the city, whether they live and/or work downtown or are tourists with little knowledge or experience in Santa Cruz.
“I want to do a blend of architecture, nature and culture,” said O’Leary. It’s through these three elements that he plans to tell a fuller and broader story about Santa Cruz and how it came to be — everything from the Indigenous people of the area, to the Spanish and Mexican periods, on through to post-statehood settlement and more recent decades.
O’Leary also brings his own personal experience with local history to the tours. He grew up in the 1970s on the Westside, a short walk from downtown, and attended Santa Cruz High School in the 1980s. He is a living witness to pre-earthquake Santa Cruz.
“The focal point back then was the Cooper House,” he said of the former county courthouse at Pacific Avenue and Cooper Street that was demolished shortly after the 1989 Loma Prieta earthquake. “I would go down there as a kid and just listen to the music and see all the people just hanging out.”
In the mid-2020s, with all the construction and grand plans in the works, a walking tour can be a valuable moment-in-time experience as well. O’Leary is careful to keep his tour from sinking into nostalgia. “I like to celebrate the past, but I’m not one of those people who’s only looking back,” he said. “I’m open to new people coming in to bring new energy and ideas, which makes this town what it is. I think, within reason, I’m OK with these [new] buildings going up. As you look at history, you’ll see that this town used to be a bunch of potato pastures. It’s always changing.”
Walk Santa Cruz’s 90-minute downtown walking tours take place Friday, Saturday and Sunday, at 10 a.m. and 2 p.m. each day.
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