Looking to take your road riding in the Bay to the next level? Hunt down Old Railroad Grade as it winds up to the eastern peak of Mount Tamalpais in Marin County. This picturesque trail offers an exhilarating combination of far-reaching views, history and challenge for road and mountain cyclists alike following the route originally carved out for the Mt. Tamalpais Scenic Railway, which opened in 1896 as the "Crookedest Railroad in the World."
At 2.5 miles in, you'll come to the West Point Inn - a great place to recharge, have a snack, and take in the view that includes part of East Bay, the Golden Gate Bridge and San Francisco. The West Point also has pancake breakfasts..! (See link below!) Most riders include a stretch on Railroad Grade as part of a larger ride, but its certainly worth a spin no matter what.
From San Francisco, take Highway 101 North across the Golden Gate Bridge. Continue on Highway 101 to the Highway 131/Tiburon Boulevard/East Blithedale exit toward East Blithedale Avenue. Continue on East Blithedale Avenue for about 2 miles. Turn left at Throckmorton Avenue, and soon after that turn left on Lovell Avenue. Turn right to stay on Lovell Avenue, then turn right again onto Summit Avenue. Make a sharp left onto Tamalpais Avenue and continue on Tamalpais. Make a slight right onto Summit Avenue and continue on Summit. Turn left on Fern Canyon Road. The trailhead is at the end of Fern Canyon Road; look for the gate. Park on the street.