1. If you begin by BARTing from Fremont to Orinda in the morning, you will be met by a Cherry City member with your BART ticket and Route Sheet – which you can study while riding to the start. See our BART information pages for the best times and tips for the BART trip. From the Orinda BART station you ride ¼ mile North along a set of pedestrian paths bridges and paths to the Community Park (by the library and Café Teatro).
2. The ride starts at Orinda Community Park (¼ mile North of Orinda BART) between 6:00 and 8:00 AM. You will travel North 12 miles along a nice level warm-up with great scenic views of the reservoir and hills – then back East and South through winding oak-grassland hills. There is a big climb along Bear Creek Rd. (mama bear of the popular “Three Bears” bicycle route) and an even steeper one as you go up and over Happy Valley Road. You will find the Happy Valley climb and descent very memorable, and you should be extremely careful on the descent as it is steep and winding with a dangerous road surface until you get to the level part. From Happy Valley you turn right and return back to the Orinda starting point through some pleasant Orinda neighborhoods.
3. After visiting the Orinda Park foodstop (where you started) go North again for two miles on Camino Pablo. This time you turn left and climb for 3 miles up Wildcat Canyon Road to Inspiration Point. You can go into the parking lot there to see a great view of the oak-grassland hills as far as you can see to the North and East. Then a gentle descent through the Eastern part of Tilden Park, bottoming at the Botanic Gardens and The Brazilian Room. This whole section through Tilden Park is through impressive groves of Eucalyptus trees.
4. Next you will climb Grizzley Peak. You can go up along Shasta Road then left onto Grizzley Peak Blvd. Or you can take a very difficult shortcut by turning left at the bottom of Wildcat and go up South Park -- this will take you straight up in just two miles instead of 5 miles: a very difficult climb. From the top of Grizzley Peak, the great panoramic bay views start -- but on the descent you must be cautious – to enjoy any of these views you should stop at any of the many pull-outs; you cannot pay proper attention on this high-speed dangerous descent and watch the views at the same time. There are lots of good places a little further along where you can enjoy these bay views more easily and safely.
5. At the bottom of Grizzley Peak Blvd. there is a 4-way stop. At the very top of the first hill after that stop sign, as you go around the corner, you can pull off on the right for the very best bay view. Here you can see all four main bridges – and even the Farallon Islands on a very clear day.
6. Continue South up and down along Grizzley Peak Blvd. At mile 30 it intersects with Skyline Blvd. A short distance down Skyline is The Sibley Volcanic Preserve. There are good restrooms with sinks and running water here (important to know if you are riding these roads without our support).. Continue South down Skyline – another nice descent with panoramic views.
7. At mile 32 look for Pinehurst Road: a hidden left turn at a 5-way intersection. This is where you leave the ridgetop and dive down into the redwood forests of Canyon. This is a steep descent with a poor quality road surface, and three or four 180 degree hairpin turns that you should watch out for. Then at the bottom it is level for a couple of miles, after which you will find our Canyon School food stop (mile 44). This stop is deep in the cool and beautiful redwood forests of the tiny town of Canyon.
8. Next up and over lower Pinehurst Road – climb #6. This descent is fairly dangerous, because the steep double-S turns are banked allowing you to build up much higher speeds than you would normally enjoy – so be very careful here.
9. Up and over Redwood Road – climb #7. Just the usual dangerous winding descent. Be watchful for loose gravel and rocks.
10. After the last short steep climb on Redwood (past the golf course),
you descend into the city of Castro Valley. Observe the speed limits
and switch to urban-defensive riding mode as you pass through the city.
Turn left onto Heyer just before the big new Center for the Arts on the
right – to avoid the downtown traffic. In a few more miles you
go onto Paloverde Rd., then turn right into the Palomares School food
stop (mile 60).
11. Climb up and over Palomares – climb #8 – 5 miles up; a long, fun descent – but note that as you reach the bottom of the long descent it keeps getting steeper and steeper, so the sharp winding turns are suddenly coming very fast -- watch for that and be ready to brake when you reach that part.
12. Next you will transition suddenly from a deserted rural road to a high-speed highway. Make that left turn very carefully, and ride along the beautiful but dangerous (due to speeding traffic) Niles Canyon Road. Be especially cautious on the two bridges that have no bicycle lanes at all. When you reach the small town of Sunol, the exit takes you right to the Community Park where we have our food stop.
13. Next you will climb up and over Calaveras – climb #9 – 12 miles up; with a false summit at 8 miles, another at 10; and a short steep descent. At mile 93 you will find our next Beverage/Food stop – at Mt. Olive Church, on right at E Calaveras Blvd and Evans Rd.
14. If you are considering the optional extra loop that climbs the CAT 1 Sierra Road then descends back to the same Mt. Olive Church stop, you should carefully evaluate your status at this time. Unlike the previous climbs, the CAT 1 climb can damage you if you are not up to it! Be sure to notify the Cherry City Registrar at the Mt. Olive Church stop if you intend to go on the extra 16-mile loop, and then check back in on your second time through. If you turn around on Sierra and proceed on to the finish, be sure to notify the Registrar there so we are not conducting a Search and Rescue effort looking for you on Sierra Road while you are eating at the restaurant in Fremont!
15. Proceed about 16 miles along level and light rollers back through Fremont to the finish – at Walnut and Paseo Padre. We provide valet bicycle parking while you eat in the restaurant. Be sure to check in with the Cherry City Registrar even if you don’t plan on eating there – you can exchange your wrist band there for your BART ticket back to Orinda.