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.

Directions

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. Continue reading →