Day Trips and Sips: Pair a Hike with a Winery on Cupertino’s Montebello Road


By Ben Lilly

Jan. 2, 2024—Hilltrompers, we have good news: you don’t have to schlep to Napa or Sonoma to enjoy a day brimming with rural landscapes and local wines. Instead, just hit the vineyards of Cupertino.

This corner of the Santa Clara Valley is a well-kept secret. Since Montebello Road dead-ends at the top rather than connecting to Skyline Boulevard, it’s not on the way to anywhere. But the trails that start from the end of the road are precisely our destination on this Trips & Sips adventure.
There’s only one parking option for hikers at the top of Montebello Road—the Water Wheel Creek Permit Parking Area, managed by the Midpeninsula Regional Open Space District (Midpen). The gate to the lot is kept locked, but Midpen will share the code with prospective visitors free of charge as long as they apply for a parking permit for the day they wish to hike. Permits generally take two business days to process; this means that to do this trip on a Saturday or Sunday, you should ideally apply for a parking permit by Wednesday. Get your permit here.
As a Plan B, Ridge Vineyards and Vidovich Vineyards are both close enough to the trailhead that you could park at one of them and start your hike from there. Please only park at one of these wineries if you also plan to taste, and always check with them that it’s okay to park early for your tasting (or stay parked late). And please note that Vidovich is open only on Saturday and Sunday.
If you’d rather use a taxi, contact the winery you plan to visit for a recommendation. Do not rely on rideshare services, as it’s often impossible to get a Lyft or Uber from the top of Montebello Road.
Suburban Cupertino is not exactly café country, but Voyager Craft Coffee (20807 Stevens Creek Boulevard, (408-320-2325) proudly carries the torch. Surrounded by strip malls, the shop’s terrace nonetheless manages to feel inviting with its pastel-colored tables and chairs—and it’s pleasantly packed at all hours of the day. Depending on where you’re traveling from on your way to Monte Bello, this pit stop is likely about a 10-minute detour.
If you parked at Water Wheel, you’ll start hiking on the Waterwheel Creek Trail, which hugs the hillside and alternates between sweeping views and more shaded sections as it passes over a series of wooded arroyos. In spring, the open fields and the tall hedges of chaparral plants such as chamise burst with wildflowers. In winter, the same fields serve up a neon filigree of the rainy season’s eye-popping greens; in summer the grass is baked golden-gray, from which the arroyos offer a mossy, fragrant reprieve.
After 1.5 miles you’ll come to a T intersection and turn left on the Montebello Road Trail, a wider fire road shared with mountain bikers. From here it’s another mile of gradual climbing up to the summit of Black Mountain, a wide hilltop marked by a series of cell phone towers and a field of boulders where you can sit and have a snack. 
The views are expansive, taking in the waters of the San Francisco Bay and iconic Peninsula buildings such as the Moffett Field hangars and Stanford University’s Hoover Tower. In the other direction you can glimpse the ocean in the distance.
Return on the Montebello Road Trail, a much more direct route back to the end of Montebello Road, for a 3.2-mile loop. Or you could about-face on the Waterwheel Creek Trail for a 5.2-mile out-&-back. If you’re looking for more miles, continue past the summit to the Black Mountain backpacking camp (0.3 miles one way) to use the restrooms and snack at picnic tables. Or add a lollipop loop of your choice on one of the many Monte Bello Open Space trails that branch off from this spot (a map can be found here).
Vidovich Vineyards
The newest vineyard on Montebello Ridge and the closest one to the trailhead, Vidovich Vineyards (18101 Montebello Road) was planted in 1996 as a project of the Vidoviches, a land-owning family with deep roots in the Santa Clara Valley farming industry. The project is managed by a winemaker originally from New Zealand, Steve Timmins, and the calling card of their tasting room is big views. 
Since opening, Vidovich has focused on cabernets, a grape which grows best on rocky and well-drained soil like the kind found on mountaintops. Their cabernets are rich, bold and thick with tannins, and get excellent reviews. Open Saturday & Sunday 12 noon–5 p.m.; tastings $25 per person by appointment only; charcuterie available for sale separately.
Ridge Vineyards
Ridge Vineyards (17100 Montebello Road; 408-868-1320) is Montebello’s illustrious grande dame. One of their wines was a contestant in the 1976 Judgment of Paris, the blind tasting in Paris, France, which put California wine on the map when top French wine critics unknowingly rated California wines as the best in every category. 
Everything about Ridge is understated: the simple black-and-white labels on the bottles are unchanged in design since the ’70s, and the barn-style tasting room is rustic and calming, with only the occasional chic touch to remind you of the property’s prestige. 
Ridge is no one-trick pony: they’re known for their Cabernet Sauvignons, Zinfandels and Chardonnays, but create a number of intriguing blends from both their Montebello vineyard and properties in Napa County. Often these blends showcase less well-known grape varietals. The best part: the tasting menu changes every few months, so you can visit throughout the year and discover different types of wines from Ridge’s inventory. Open every day 11am–4pm; “Estate Tastings” $30 per person; “Private Library tastings” $75 per person at 11am and 2pm; both by appointment only; charcuterie available for sale separately.
Picchetti Winery
If Ridge is the grande dame of Cupertino winemaking, Picchetti Winery (13100 Montebello Road, 408-741-1310) is the charming nonna and matriarch. The Picchetti brothers, Vicenzo and Secondo, were the ones who named the ridge on which they built their ranch “Monte Bello.” Feral peacocks roam the garden, the descendants of a bird-keeping hobby started by Vicenzo's son. 
(What were once the estate's extensive grounds are now a small preserve, Picchetti Ranch Open Space. This property is much closer to the bottom of the mountain than the other two, so if you opt to come tasting here you might consider a short hike directly from the winery rather than our recommended one atop Black Mountain.)
Sadly, the winery ceased to be profitable during Prohibition and the Picchetti family had to sell. It was preserved as a historical monument for many years (and even used as a filming location for a spaghetti western with Julia Roberts, Blood Red) before being purchased and re-bonded by Leslie Pantling in 1998. 
To taste Picchetti’s wines—which are only sold on site— is to taste a phoenix of the oenological world: once vanished, now reborn from the ashes. Open every day 11am–4pm; tastings $25; reservations not required.