Drive Monterey Road between San Martin and Morgan Hill on a Saturday in October and you will pass, in the span of about two miles, a pepper farm dressed up as a pumpkin patch, three wineries that could not be more different in scale, a golf resort hosting a country music series, and a small airport where strangers pay to jump out of an airplane for fun. None of these places started out trying to be a destination. That is the thing worth understanding about how fall actually works here. San Martin's calendar was not planned by anyone chasing foot traffic. It was assembled, almost by accident, out of businesses that scaled up from something smaller and just kept going.
The Farm That Grows Peppers Ten Months a Year
The pumpkin patch most people know as Uesugi Farms Pumpkin Park is only open for one month. It opens October 1 and closes after Halloween. The rest of the year, that same ground and the operation behind it are doing something else entirely. Uesugi Farms' real business is peppers, along with Napa cabbage, sweet corn, strawberries and beans, farmed across roughly 1,500 acres in California and another 700 in Mexico, most of it leased land stretching from Coyote Valley down to Gilroy. The pumpkin seeds go into the ground in late May and the harvest wraps by early fall, timed so the crop is ready right when families start showing up for hayrides.
The name itself carries history that most visitors driving past the marigold fields never hear. The farm is named for George Uesugi, a Japanese-American grower whose land was taken from him and who was sent to an internment camp during World War II, despite having fought for the United States. He rebuilt a vegetable business in the 1950s and sold it to the Aiello family in 1979. Joe Aiello started the pumpkin side of things in 1985, mainly to give his sons Pete and his brother something to do after school. It worked. What began as a way to keep two kids out of trouble is now a fixture with a two-acre corn maze, a hayride through fields of marigolds and sunflowers, pumpkin cannons, a mini train and an annual Giant Pumpkin Weigh-Off sanctioned by the Great Pumpkin Commonwealth. Past contests have produced entries topping 1,900 pounds, including a world-record 2,032-pound pumpkin weighed here in 2013.
None of that scale was the point when it started. It grew because people kept coming back.
Three Wineries, Three Different Sizes, One Road
San Martin's wine scene tells a similar story of things that got bigger than planned, except here you can see three different stages of that growth within a few minutes of each other.
Clos LaChance Winery started in 1987 when co-owners Bill and Brenda Murphy planted a few rows of Chardonnay in their Saratoga backyard. The wine was good enough to sell, and by the time the winery released its first vintage in 1992, the operation had grown from 200 cases to 80,000 and from three quarters of an acre to 150 planted acres. Today the tasting room sits on Hummingbird Lane in San Martin, next to the sixth hole of CordeValle Golf Club, open to the public Wednesday through Sunday for tastings, tours, picnicking and bocce ball.
A few miles away, Lightheart Cellars is what Clos LaChance looked like decades ago. It is a genuinely backyard-scale operation, with a tasting room set up at a residence, and it shows up alongside places like Ross Vineyards during a countywide passport weekend, when small producers across the valley open their doors together for a run of tastings. If Clos LaChance is proof of what a backyard vineyard can become, Lightheart Cellars is the reminder that most of them stay exactly what they started as, and that is fine too.
The Concert Series That Didn't Have to Travel Far
CordeValle, the golf resort that shares a property line with Clos LaChance, runs a recurring outdoor concert night called the KRTY Song and Wine Series. It is not a one-off festival. It is a Thursday and Friday habit that has run through the summer and into fall, with 2026 dates that included shows on August 6 and 7, September 10 and 11, and running through October 1 and 2. Past KRTY nights at the property have brought in touring country acts, and the series works precisely because it doesn't ask anyone to drive far. You can watch a set, walk the grounds, and be back on Monterey Road in the time it would take to find parking at most Bay Area amphitheaters.
That is the pattern again. Nobody built a concert venue from scratch out here. A golf resort with a wine-country backdrop already existed, and the series slotted into a Thursday night slot that was sitting open.
Watching Strangers Fall From 18,000 Feet on a Saturday Afternoon
The oddest entry on this stretch of road is also the one most locals have driven past without quite registering what it is. San Martin Airport, a small county-operated airfield right off Highway 101, is home to Skydive Silicon Valley, a full-service tandem skydiving operation whose founders, Ronaldo and Vitor, started their skydiving careers back in 1996. The business has been under new ownership since 2017 and now flies its tandem jumps out of San Martin Airport's south entrance.
What makes it worth mentioning here, rather than in a list of things to do, is that it is not framed as a tourist stop at all. It is a working drop zone that happens to run open to the public. Jumps go up to 18,000 feet, described as the highest skydive and longest freefall available in California, with views that stretch to the San Andreas Fault, Monterey Bay and, on a clear day, the Sierra Nevada. The drop zone is closed only on Tuesdays. You do not need to jump to get something out of it. Plenty of residents just pull off and watch, because a parachute opening over a farm road on an otherwise quiet Saturday is the kind of thing that is hard not to look up at.
What Actually Ties This Together
None of these places set out to be part of a shared fall season. A pepper farmer's sons needed something to do after school. A backyard Chardonnay hobby got good enough to sell. A golf course booked a concert series to fill Thursday nights. Two skydivers who started jumping as teenagers turned it into a career. Add them up and you get a stretch of Monterey Road that does more on a single October Saturday than most planned entertainment districts manage in a season, and it does it without anyone trying to build a destination.
That is worth knowing if you already live here and have only ever driven this road on the way to somewhere else. This year, the overlap lands squarely on the first weekend of October: Uesugi Farms opens its gates for the season on October 1, the same weekend CordeValle runs its October 1 and 2 Song and Wine shows next door. Pair that with a Saturday tasting flight and a Sunday morning watching jumpers drop over the airport, and you have covered the whole stretch in one long weekend, something that does not line up the rest of the year.
If San Martin's mix of working farms, small wineries and wide-open parcels is part of what drew you here in the first place, and you are curious what that same character looks like on the real estate side, from ranchettes to vineyard-adjacent lots, Erica Trinchero and the SoldByErica team are always glad to talk through what is actually on the ground in San Martin right now. Book a Consultation whenever you are ready.
