On September 5, neighbors gathered at Westwind Community Barn for the town's annual Hoedown: bluegrass from a live band, barbecue smoke drifting past the arena, kids watching riders put horses through their paces before dinner. Nobody walking in that evening was thinking about pathway easements. They were thinking about dinner and the band.
But the paths that got most of those neighbors to Altamont Road that evening are not fixed the way the barn's hitching posts are fixed. Los Altos Hills built its identity on roughly sixty miles of unpaved trail instead of curbside sidewalks, a trade the town made decades ago to protect its one-acre zoning and rural feel. Ask a longtime resident what makes this town different from Los Altos or Portola Valley, and the pathways come up before the schools or the lot sizes. What most residents don't track, because there's no reason to unless you sit through the meetings, is that this system is still being built and still being argued over, one street at a time, by a volunteer committee that meets in a conference room at Town Hall.
One-Acre Lots, Zero Sidewalks, One Standing Committee
The town's founders made a specific bet: keep the one-acre minimum lot size that defines the community, and route pedestrians, runners, cyclists, and horses through a shared path network instead of paving sidewalks along every road. The town's own description of the system frames it around what it calls the three C's: common sense, courtesy, and communication, since bicyclists are expected to yield to horseback riders and pedestrians yield to horses in turn.
That informal code works because a standing Pathways Committee exists to handle the cases where common sense runs out. The committee met through the spring and summer of 2026 with members Nick Erndt, Mike Orlando, John Lewis, and Marc Gurwith working through a backlog of signage requests, easement disputes, and construction timelines, often with a Town Council liaison sitting in. This isn't a body that convenes once a decade to redraw a map. It's active, and its decisions this year are shaping which paths residents can actually use.
The Case of Chaparral Road
The clearest example of a path still being negotiated rather than simply maintained is Chaparral Road. Residents there have maintained that stretch of gravel for nearly sixty years, and this year they brought a formal complaint to the Pathways Committee over cyclists using the unpaved road in ways they consider unsafe, describing past near misses on a road with a documented seven-foot pathway easement that, in their account, the town never widened or maintained to match.
The committee walked through several fixes: a modified speed limit sign, a dangerous-curve warning, a private-road marker. No option produced consensus in the room, and the matter was sent up to the full Town Council rather than resolved at the committee level. That's not a bureaucratic footnote. It's the system working exactly as it's designed to work when a shared, unpaved trail absorbs more bike traffic than it was ever built to carry, and the people who show up to argue about it are the same residents who'll use whatever gets decided.
A few miles away, where the Robleda and Conception paths meet at a summit with limited sightlines, the committee handled a similar problem with less friction this year. New warning signage was installed for the stretch where bikes, horses, and pedestrians all converge, and after a positive early report on the install, staff placed an order for additional signs. Same underlying tension between trail users, a much shorter path to resolution.
Where the Money Actually Comes From
Here's the part that surprised me most in the research: the pathway fund isn't drawn from general property taxes. It's financed by a fee charged whenever a property owner redevelops or expands a home enough to trigger the town's pathway dedication requirement, and it currently brings in roughly $900,000 a year. That means the pace of pathway construction tracks local remodeling and rebuilding activity, not a fixed municipal budget line. When building slows, so does the path system's expansion.
Right now that fund is financing three concrete projects. A roughly 2,000-foot pathway on Magdalena Avenue, estimated at $350,000 to $400,000, is slated for construction this summer, with the committee also voting to preserve an existing homeowner-built pathway at 10285 Magdalena Avenue while the work proceeds. A parallel project on Summerhill Avenue is targeted for the same window, pending county comments and an encroachment permit. And on Altamont Road, between Moody Road and Corbetta Lane, the segment has been staked, the right-of-way confirmed, and a biological study commissioned ahead of tree removal, with a first phase built in-house by town crews and the project expected to reach the Planning Commission and Town Council by mid-summer.
None of this means the system is broken. It means it behaves less like finished infrastructure and more like a running civic project, funded steadily but built in fits and starts tied to the town's own growth.
The Paths Actually Go Somewhere
For all the committee business, the reason residents care is that these paths connect to places worth walking to. Westwind Community Barn, where the Hoedown was held this month, sits on land the town has owned since 1976, when Countess Margit Bessenyey donated the property she had used to breed and train Hungarian horses alongside renowned trainer Linda Tellington-Jones. A 2009 renovation brought a new dressage court and jumping arena, and the barn's interscholastic equestrian team finished last season as Region 4 high-point champion for both its middle school and high school divisions.
Directly adjacent sits Byrne Preserve, grassland and oak woodland that holds the headwaters of Moody Creek. Whatever is or isn't resolved on Chaparral or Magdalena, the preserve's Artemas Ginzton Path keeps working: a loop of roughly 3.1 miles that crosses the creek, climbs through bay laurel and oak, and passes open pasture where Westwind's horses are turned out to graze. Grassroots Ecology leads volunteer restoration days there through the year, and the nonprofit occasionally schedules after-dark outings built around spotting the preserve's nocturnal residents.
Further out, the same trail network eventually reaches Hidden Villa, the 1,600-acre working farm the Duveneck family founded in 1924 and donated to the public upon Frank Duveneck's death in 1985. Its trails connect onward into Rancho San Antonio, and for residents who visit often, Hidden Villa sells an annual Access Pass good for free, unlimited admission from September through May, a season that just opened.
Reading the System Through the Rest of This Year
If you're planning a fall walk and want to skip the committee drama entirely, the Byrne Preserve loop via the Artemas Ginzton Path is the safest bet regardless of what's happening on Chaparral or Magdalena. If you're a regular on Robleda or Conception, expect to see more signage before winter. If you live near Altamont between Moody and Corbetta, this summer's completed biological survey is the signal that construction is close behind. And this spring's 24th annual Pathways Run/Walk, which started at Westwind Barn and looped through Byrne Preserve before extending into the wider path system, will be back again next May, the one weekend a year when the whole network gets used at once instead of one committee agenda at a time.
None of this is a reason to think less of the system. It's the opposite. A town that could have paved sidewalks decades ago and called it finished instead built something that still requires neighbors to show up and argue about a gravel road, and that argument is, in its own way, what keeps the paths worth walking.
Dana Rae Stone has spent years building relationships across Los Altos Hills, Woodside, Atherton, and the rest of the Peninsula, the kind that come from paying attention to a town's actual rhythms rather than its market summary. If you're thinking about your own place in this community, Dana Rae Stone would love to talk about your home.
