Things to watch for and to watch out for:
General Police Presence
Note that the cities of Orinda and Lafayette are going to monitor our event, so be sure to observe the rules of the road when riding through those cities -- be sure to observe the stop signs, signals, and the speed limit when descending Santa Maria back into central Orinda (at the end of the initial 24 mile loop).
Dangerous Descents and Roads
The Happy Valley descent (the first mile of it) is the most dangerous of the many descents on our route, due to extensive damage to the road as well as being extremely steep and winding. Other dangerous descents are Grizzley Peak, upper Pinehurst, lower Pinehurst, Redwood Road, Palomares Road, and Sierra Road. Grizzley Peak is a great descent, but it is fast, has traffic, and it has fabulous views that you should not let distract you from your attention to the road -- you will see lots of those same views later where it is safer. Upper Pinehurst starts steep and fast, so you speed right into a full 180 degree hairpin, then it levels off and has rough road quality for the rest of the descent. Lower Pinehurst has steep banked S and double-S curves, and at the ending stop sign watch out for bicycles speeding down Redwood Road from your right -- they are much more of a danger than cars you can hear coming. Redwood Road is pretty tame after those others, but it's descent is more than two miles long. Palomares is fine until you reach the last couple of miles, where it gets increasingly steep and winding, with lots of gravel -- you should be ready with your brakes as you go into those steep curves.
Also, the stop sign at Palomares and Niles Canyon signals a sudden transition from country road to high-speed highway, so change your riding style accordingly! That can be quite a dangerous left turn, because the high-speed traffic is not very visible -- and those fast-moving cars are not expecting bicycles to be pulling out in front of them.
The last dangerous descent (optionally) is Sierra Road -- a long and very steep road after your exhausting climb, so you must be extra careful because you will be very tired by that point -- even after resting at the top!
All of these descents are quite fun for advanced riders, and are only dangerous if you ride too fast for the conditions. All of these roads require your full attention if you are going fast: they all have bad bumps and defects, and lots of sharp corners where you should be ready for rocks or gravel on the road.
BOB's Best Places
City of Orinda
This small town is a relatively unknown jewel, with some great shops and cafes, surrounded by great bicycle routes on all sides. It makes a great start and/or finish point to a ride, whether you drive to it or utilize BART.
Three Bears Ride (CCW vs CW)
One of the most popular bicycle rides in the East Bay starts in Orinda and goes around Camino Diablo, Castro Ranch Road, Alhambra Valley Road, and Bear Creek Road. The Bear Creek Road is the hilly part, although it is a little difficult to discern just three main hills there. If you do the loop in the other (CCW) direction the hills on Bear Creek Road are quite different and even more challenging - and they start in a big way after a mere 2 miles to warm up.
Happy Valley (& Lafayette BART)
The ride from Bear Creek Road up and over Happy Valley Road and down into Lafayette is one of the steepest climbs and most fun descents around. It was one of the KOM (King of the Mountain) climbs of the 2006 Tour of California. When you do it you are guaranteed to remember it for a long time. Note that the opposite direction is not a bicycle-friendly route, due to the miles of heavy traffic and lack of road-shoulder -- going down that at high speed is ok, but it's not so good for a slow climb.
You will find this park very nice to ride through: scenic and serene, with endless stands of huge Eucalyptus trees. You will ride past Inspiration Point, the Botanic Gardens, and the Brazil Room - a very popular venue for events such as weddings and funerals. Actually, that is just a part of the park; there are many other areas that are more populated and trafficed. As you go by the Botanic Gardens at the bottom of the Wildcat descent, note the intersection with South Park Blvd. -- renowned among local bicyclists. If you turn left there you will climb up South Park straight to the summit of Grizzley Peak and intersect our BOB route there, but via a much steeper, very long continuous climb.
Pinehurst and Redwood Roads
Pinehurst Road is very popular with bicyclists. But there are actually two parts, generally referred to as upper and lower Pinehurst. Upper is the part from Skyline to the Canyon Road intersection - on the BOB ride it is just one long descent. When ridden in the opposite direction, it is a climb that increases in difficulty to around a 12% slope at the top section. Lower Pinehurst is a climb and descent that takes you to the popular Redwood Road. It is very common to ride both Redwood Road and Lower Pinehurst from Castro Valley to Moraga and to various destinations from there. Other popular variations are to ride Redwood Road and all of Pinehurst up to Skyline Blvd. then go left and later back down Redwood Road (from where it intersects Skyline) or turn right on Skyline (and do the BOB ride in reverse).
Town of Canyon
Located on Pinehurst Road, this tiny picturesque town is stuck in time, isolated by how difficult it is to reach. There are always far more bicycles going through Canyon than cars. All that remains now is the post office and the school, and a very few residents. The school draws from all around - it's quite a different option than the usual public school. And the redwoods that are a wonderful feature of Canyon are still recovering from the logging that decimated them in the early 20th century; it's so nice now: those original giants must have really been impressive..
Another of the popular routes of the East Bay, it is common to ride from Castro Valley BART over the Dublin Grade (frontage road) to Pleasanton, down Foothill to Sunol, then along Niles Canyon Rd. and back up and over Palomares back to Castro Valley.
Niles Canyon is very scenic, and is a great bicycle route except that it suffers from excessive high-speed traffic and little room for bicycles in some areas. Some bicyclists avoid it because of these issues, but many others do use it because it is the best route going East or West in that area.
Town of Sunol
Another quaint town with lots of personality, including old steam trains that run through Niles Canyon on the weekends, a wonderful park, and great bicycle routes going off in every direction. Sunol is also famous for having a dog as their mayor some years back.
This road is among the most popular and well-known of all of the parts of the BOB route. It is the right type of road for great cycling, with little traffic and lots of great scenery. It has the right length, the right amount of climbing, with enough variation to offer a little of all types of riding. It even has a huge, interesting tree farm that you ride by for miles, viewing species after species of trees being raised.
This is simply the most infamous climb around, known far and wide for its seemingly endless and relentless CAT 1 climb. At 4.2 miles of a constant 15 to 17%, it was the most challenging climb on the entire Tour of California of 2006 and 2007. It also offers a fabulous ride along the summit with 360 degree panoramic views and one awesome descent.