Rolling out on a two-up bike lane on Sandhill Road, this route crosses I-280 to cruise on tree-lined roads with minimal traffic. After emerging from shady Manzanita Way, embark on a 14-mile out-and-back stretch on Cañada Road. The shoulders are wide on Cañada Road, but the road is especially bike-friendly from 9 a.m. to 3 p.m. on Sundays -- it’s closed to auto traffic. This stretch past the Crystal Springs Reservoir is perfect for working in a paceline. On the return, head south to loop through Portola Valley's verdant hills. This route is a favorite of the Stanford University Cycling team.