The BEST OF THE BAY Double Century can be broken down into the following three segments:

• A 53-mile rural and scenic trip from Castro Valley through the East Bay hills, up and over Grizzly Peak, returning through the hills to our headquarters in Castro Valley. You will see panoramic views of the entire SF Bay, first in the dark and then again on the return as the sun is coming up over the bay.

• A 53-mile ride from Castro Valley to Mt. Diablo, climbing up South Gate Road, descending the same road, and followed by a lessor climb up Bollinger Canyon Road to our lunch stop at Las Trampas Regional Wilderness.

• A 91-mile ramble south on Bollinger Canyon Road, San Ramon Valley Boulevard, and Foothill Road to the Sunol-Ohlone Regional Park rest stop. The route then heads through Pleasanton, and continues east through the Livermore vineyards, and north on Collier Canyon Road towards Mt. Diablo. This time you won’t climb Mt. Diablo, but cycle past it to Danville, before heading south to Dublin, and finally descend to the finish in Castro Valley.

Segment 1: Castro Valley to Grizzly Peak and Back

The BOB Double Century begins with a journey north through the East Bay hills to the top of Grizzly Peak, high above Berkeley. The roads are all rural, winding, hilly, and scenic with sweeping panoramic views of the San Francisco Bay, first in the dark and then again on the return as dawn is breaking over the bay.

Warning: early in the morning, many of these roads may be damp and slippery.

The first climb and descent is Redwood Road, a beautiful rural winding road with little traffic. At Skyline Blvd turn right and it will take you through several large parks and lots of miles overlooking the entire bay. After you turn right onto Grizzly Peak Boulevard, you will have even better views of the Bay for several miles, descend to a four-way stop, then you will head up the final climb up to Grizzly Peak. At the top you will pass the popular steam trains (part of Tilden Park) and begin a long fast winding descent through woodlands into Tilden Park to the turn- around rest stop at ISLAND picnic area.

As you return you will again see those majestic views of the San Francisco Bay but this time as the bay is waking up to the sun rising. The descent down from Grizzly Peak is memorable, reminiscent of some descents into Italian and French coastal cities; it is hard to keep your attention on the road. About a third of the way back you will dive down the very steep and curvy descent of Pinehurst Road, into the quaint town of Canyon nestled deep in a hidden redwood forest, then another up and over climb on Pinehurst, and a final up and over climb back along Redwood Road, to BOB headquarters for breakfast (rest stop #2).

Segment 2: Castro Valley to Mt. Diablo to Las Trampas Regional Wilderness

This segment features the greatest challenge of the BOB Double Century – climbing rugged and pristine Mt. Diablo. Bicycling Magazine has noted this ascent on its list of the ten best mountain climbs in the U.S. The climb is difficult, but hugely famous and popular for advanced cyclists. The views from the summit are renowned for how far you can see unimpeded in every direction.

From Castro Valley, travel east through Crow Canyon to Norris Canyon, a hidden cycling gem that takes you across the East Bay hills to the foothills of Mt. Diablo. At the bottom of the Norris Canyon descent, make your way back to Crow Canyon Road and climb up to the city of Blackhawk, where the road changes its name to Blackhawk Road. Climb over a little saddleback before turning onto Mt. Diablo Scenic Road to begin your ten-mile ascent of the mountain.

From here it is just you and the road and the increasingly awesome views in every direction. Pace yourself because the climb is long and steep. You will experience the pattern of steep climbing, levels of relief, and hairpin turns, as you traverse up the mountain. After repeating this sequence , you will arrive at the gatehouse where cars must pay a fee, but cyclists can freely pedal through. After the gatehouse, the road levels for over a mile. At the horse-crossing, you pass the helipad and have a one-mile steep climb up to the junction, where restrooms and water are available,. Continue up the climb another 4.5 miles to the Summit Picnic Area and our rest stop #3 (note: the rest stop is at the lower parking lot that has all of the picnic areas; many riders optionally ride up to the summit first, then return down 500 feet to the rest stop).

Be sure on the way down the mountain to go left at the Junction, so you return down South Gate Road – the same way you came up.

Descending the mountain is thrilling and great fun, but also a time for caution. Park rangers enforce the speed limit and will also ticket reckless riders. There are many sharp corners and blind curves that entice you to enter them too fast. Be aware that the descent is long and winding, and that your brakes may overheat.

At the bottom of the descent, after the school, you will come to a stop sign: turn right onto a downhill stretch of Diablo Road. Use caution on this rural road, where motorists tend to speed. After the descent, you will wind through the back streets of Danville and onto rider-friendly San Ramon Valley Boulevard. Continuing on this road for a number of miles, you eventually turn right onto Deerwood.

From Deerwood turn right onto Bollinger Canyon Road which will take you through the hills to the Las Trampas Regional Wilderness (Bollinger Canyon Staging Area) – our rest stop #4. Lunch will be served in a nice tree-shaded picnic area at the end of the road. Along this road you may be able to see several ostriches and a large flock of up to 75 turkeys.

Segment 3: Las Trampas Regional Wilderness to Sunol-Ohlone Regional Park to Robertson Park to Danville to Castro Valley

With all of the major climbing of the BOB Double Century route behind you, the second half of the BOB consists of 91 miles that take you through relaxed top-notch cycling roads. The climbs of this section are short and gentle.

After lunch, you start with the descent down Bollinger Canyon Road. When you get to Crow Canyon Road, look for the special button to trigger the traffic signals and use extreme caution when crossing this intersection. Traffic on Crow Canyon Road frequently travels at high speed.

After turning off Bollinger Canyon Road, you will continue south on two roads that are popular with cyclists, San Ramon Valley Boulevard and Foothill Road. The latter road becomes increasingly rural and scenic as you near the small community of Sunol.

From Sunol, you will continue south for five miles on a flat rural road that is smooth and newly paved. Use caution when crossing Interstate 680 entrances and exits: the cars do not stop! Just where the road starts a steep climb, turn left onto Geary Road. At the end of this scenic road is the Sunol-Ohlone Regional Park – rest stop #5.

You will return along the same flat rural road and turn right on Pleasanton-Sunol Road. After a short, easy climb, you have many miles of smooth, flat pavement that takes you to downtown Pleasanton. You’ll encounter a few blocks of urban traffic before turning right onto Vineyard Boulevard which will take you east past the vineyards of Livermore.

You’ll travel through several miles of vineyards before you reach rest stop #6 at Robertson Park. As you leave the park, you will travel north, passing through downtown Livermore before again heading into the southern Mt. Diablo foothills. You’ll first ride through Collier Canyon Road, a long gentle pastoral road through cow and horse farm country. Turn left onto Highland Road, and continue through the pastoral landscape until you turn right onto Camino Tassajara Road which transitions your experience from rural to suburban. You will stay on this road for about eight miles with some gentle climbing at first, and then a long, shallow descent all the way to Danville.

After turning left onto San Ramon Valley Boulevard in Danville, you will ride for about ten miles until you reach the town of San Ramon and rest stop #7 at the intersection of San Ramon Valley Boulevard and Crow Canyon Road. The rest stop is at the Extra Mile Chevron Gas Station where you can use the restrooms and pick up any fuel you may need for the final sixteen miles to the finish.

From rest stop #7, continue south on San Ramon Valley Boulevard to the town of Dublin. Take a right on Dublin Boulevard and begin your last significant climb on this lightly trafficked road.

After the climb, you will turn left and descend Schaefer Ranch Road. The descent is short but very steep, with a stop sign at the bottom where the road intersects with Dublin Canyon Road. Be sure to stop since there is often high speed cross traffic.

On Dublin Canyon Road you’ll ride a nice long gradual downhill stretch towards Castro Valley. After the descent, you will have about five easy miles that wind through the quiet neighborhoods of Castro Valley and take you to the ride finish.

Note: All locations, times, and distances are subject to change until the day of the ride. The route sheet distributed on the day of the ride is the final and official route.