This terrifically difficult 29-mile ride is a brutal test of strength and stamina! Although it features the same overall elevation change as the Skyline Blvd route, Montebello Rd gains all 2,000 vertical feet within a short span of 5 miles.
Leave your fixed gear at home for this one, unless its gear ratio is set for intense climbing. You’ll be thankful the mechanical advantage. Bring a paper map or cached electronic map with you – internet and GPS is non-existent when it matters most up on the mountain.
The reward for your efforts is a series of wine tastings at Picchetti Winery (11-5 daily, $5 flight) and Ridge Vineyards (11-4 weekends, $5-$20 flights), and quiet vistas of vineyards nestled between mountains. Pack your own picnic, as the 5.6-mile stretch of suburban wind and dust from Caltrain to the foothills does not yield much in the way of fine cuisine, though there are a few options farther from the outlined path. When we went, clouds and rain descended by the time we arrived at the top, but on a clear day, you will be able to see miles and miles of landscape from the route.
START at Sunnyvale Caltrain stop, EXIT on southbound side of platform (towards San Jose). LEFT on W Evelyn Ave.
In 400 feet, RIGHT on S Sunnyvale Ave.
In 0.6 miles, S Sunnyvale Ave becomes Sunnyvale Saratoga Rd.
In 2.5 miles, LEFT onto Sunnyvale Saratoga Rd. This is a major traffic intersection. You will see S Mathilda Ave to your right.
CONTINUE STRAIGHT for 5.6 miles. (In 1.7 miles, Sunnyvale Saratoga Rd becomes N Sunnyvale Saratoga Rd, then in another 0.1 miles it becomes N De Anza Blvd. In 3.1 miles, N De Anza Blvd becomes Saratoga Sunnyvale Rd.)
If you want to stop for lunch or picnic supplies, there are a couple of restaurants and stores along this stretch. Additionally, you may want to continue another 2 miles south on Saratoga Sunnyvale Rd and turn RIGHT at Big Basin Way. There are more options here, including Falafel at Vienna Woods Delicatessen & Restaurant (14567 Big Basin Way), which was closed for renovation the day we went and will open again in March. We stopped at Blue Rock Shoot (14523 Big Basin Way), which had a nice selection of Fair Trade and Organic coffee. Although their food options were just standard (including a couple vegetarian sandwiches), they had cozy outdoor seating in front and on their back porch. After lunch, we took Toll Gate Road, RIGHT on Pierce, and LEFT on Mt. Eden to continue towards Montebello Rd. I would not recommend this route, as the 20-30 degree slopes were tough to climb. Instead, return to S Saratoga Sunnyvale Rd via Big Basin Way, and turn LEFT onto Pierce Rd.
RIGHT onto Pierce Rd.
In 1.4 miles, RIGHT to stay on Mt. Eden Rd.
In 0.9 miles, continue onto Stevens Canyon Rd.
In 1.4 miles, you will come around the tip of the Stevens Creek Reservoir on your right. LEFT onto Montebello Rd. Step on the gas for an intense switchback ramp that’s almost a full 180 degrees. You’ll come back down this road and continue around the rest of the reservoir on your way back to Caltrain.
You will pass signs for the Picchetti Ranch Open Space Reserve, and Picchetti Brothers Winery (13100 MonteBello Road) will be on your LEFT in 0.5 miles. The property includes picnic grounds, a nice place to rest, and a chance to fill your water bottle. If you’re already tired from the ride, or if you choose to enjoy your wine such that your motor skills are no longer at top notch, mosey back down the mountain and continue following Stevens Canyon Road around the reservoir. Doing so will save you 7.4 miles from the ride. Otherwise, go easy on the grape juice, as the hardest part of the ride – 2,000 ft of winding, bumpy road to the top of the mountain – lies ahead.
Exiting Picchetti, turn LEFT to continue on Montebello Rd. Let the climbing intensify! Follow the road for 3.7 miles until you reach Ridge Vineyards (17100 MonteBello Rd) on your LEFT. On your way up, you will pass the Mikulaco family vineyard across the street from the Monte Bello Elementary School. These grapes were used in Ridge’s 2009 Mikulaco Chardonnay. Keep your eyes out for the junked vintage cars in the ravine below.
Ridge has a beautiful picnic area at its high elevation, and you can purchase a bottle of wine to drink with your snack. The Estate Single-Vineyard flight with Monte Bello is just $20, and you can get a well-rounded taste of Ridge’s offerings.
Now that the hard part is over, you get to coast down Montebello Rd in the direction you came, and it lasts only a couple of minutes compared to the hours of climbing you put in to to the top. Turn RIGHT out of Ridge Winery, and follow Montebello Rd for 4.2 miles.
SHARP LEFT on Stevens Canyon Rd to continue around the reservoir. In 1.8 miles, continue onto S Foothill Blvd. Continue straight as S Foothill Blvd turns into Foothill Expy in 1.2 miles.
After passing two Junipero Serra Fwy on ramps, take the FIRST SHARP RIGHT onto W Homestead Rd.
In 1 mile, LEFT onto Mary Ave, which becomes S Mary Ave after you cross over S Fremont Ave.
In 3.2 miles, RIGHT onto W Evelyn Ave.
END at Caltrain on your LEFT in 0.8 miles.
This ride was inspired by “Montebello Loop” from Bay Area Biking (Brown 2007, pg 160)