Touring the East Bay Hills

By Chris Kostman

Originally published in City Sports, April 1992

This hilly ride offers spectacular views of the entire San Francisco Bay Area and Mt. Diablo, as well as wooded, windy roads with generally little traffic. It also intersects an excellent off-road riding area, offering the possibility of a combined on and off road ride.

Begin at the bottom of Tunnel Rd. (0.0 mi. / 750ft.) immediately adjacent to the west end of the 13 Freeway's Caldecott Tunnel above Berkeley and Oakland. Park at the park parking lot across the freeway or right at the beginning of the ride at the Caldecott - Tunnel - Hiller intersection on the north side of the freeway. Be sure you've got two bottles of drink and the requisite spare tube and pump, then reset your computer to zero and head east up Tunnel Road. You'll know you're in the right place when you see "Is Greg LeMond Really God?" painted on the road as you begin the climb.

Tunnel Road is the most popular road in the area for club and solo rides, so you're bound to find somebody heading your way. Be careful of construction trucks as these first few miles take you through the heart of the recent East Bay conflagration. As you continue up the climb the road changes names to Old Tunnel Road, then to Skyline Blvd. as you round the bend at Broadway Terrace (2.2mi. / 1300ft.) and leave the fire zone behind. Enjoy the spectacular views of the Bay as you finish the climb, then stay straight on Skyline at Grizzly Peak (3.0mi. / 1500ft.). After the .6mi. downhill, you'll continue along the rolling and wooded Skyline and stay straight at the Pinehurst - Shepherd Canyon intersection (4.7mi. / 1320ft.). You're now on what is known as "the Pinehurst Loop" by the locals and you'll return to this point later in the ride. You'll be riding the loop counter- clockwise, the most common direction. Riding it clockwise is known as "a reverse Pinehurst" for obvious reasons.

Redwood Gate of Redwood Regional Park on your left (5.0mi.) has water, restrooms, and payphone and provides access to "the Redwood Loop." This 9 mile mountain bike loop (south on West Ridge, up Canyon Trail, north on East Ridge) is completely encircled by the Pinehurst Loop and is always ridden counter-clockwise by those in the know.

Skyline continues to afford spectacular views all the way to San Jose and out past the Golden Gate Bridge to the Farallon Islands. At 7.0mi. you'll pass nice picnic areas and Roberts Regional Park, then head down a fast downhill with two sharp turns to the Skyline - Joaquin Miller intersection. The many parked cars on this downhill attest to the area's popularity with hikers and trail runners. Turn left at this intersection (8.1mi. / 1230ft.) and take the divided four lane road to the light at Redwood Road (8.8mi. / 1070ft.) for another left and downhill. Portions of this curvey, shaded, and bumpy road can be damp and cool, so be careful. Redwood Gate of Redwood Regional Park on your left (10.9mi. / 700ft.), has water, restrooms, payphone, and an apple tree (in season) near the Ranger Station. The south end of the Redwood Loop is accessed via Canyon Trail, the steep climb to the right at the trailhead at the main parking lot.

Continue down Redwood Road to the left onto Pinehurst (11.3mi. / 630ft.) to a 1.2mi. climb which takes you into one of the quietest and nicest regions of the area. At the summit (12.5mi. / 920ft.) you'll find the southernmost end of East Ridge Trail on the left (if you hopped on here and stayed straight, you'd pass Canyon Trail and eventually end up back at Skyline Gate). The downill on Pinehurst is a blast, but very curvey and occasionally damp, so be alert. Stay straight at the bottom at Canyon Road; Moraga and Orinda are to the right (14.0mi. / 600ft.). This section's overhanging trees provide shade and the feel of a tropical forest. Riding here, it's hard to believe that so much of humanity is just over the hill.

The hairpin to the left (16.6mi. / 900ft.) signals the start of the climb back up to Skyline. The climb does get steeper as it continues, but the view of Diablo immediately before the summit makes it worth it. At the top you'll be back at the Pinehurst - Shepherd Canyon - Skyline intersection (17.9mi. / 1300ft.) and you'll make a right onto Skyline and retrace your steps back to the start of the ride.

Enjoy the views of the Bay, especially as you begin the last climb of the ride and head back to the Grizzly Peak intersection. At the summit (19.6mi. / 1500ft.), head straight back down Skyline, AKA Tunnel Road, and return to the start. Watch out for construction trucks and cars pulling in and out of driveways. Great ride, or what?