Distance: c. 44 miles 
Elevation gain: 4510 ft

(A Best of the Best ride)

There’s a line of hills and ridges that make up the spine of the East Bay from Tilden Park in Berkeley to Fremont.  Along that line is a series of four nearly-contiguous rides, all outstanding: this ride, Palomares Road, Calaveras Road, and Sierra Road.  The Best of the Bay Century (see the regional introduction) strings them all together, with filler.  As always, I’m going to give you just the good stuff, working north to south.

This ride is really four different roads.  The first, Grizzly Peak Blvd., is one of the few rides on our list that’s city riding on purpose (i.e. not as filler).  In the beginning it’s densely populated residential, and the traffic is dangerous.  It’s not relaxing.  But there’s a magic to the Berkeley Hills that leads hundreds of cyclists to brave the dangers every day, and every time I go to the East Bay I can’t wait to jump on my bike and get up there.  The views of the Bay are unbelievable.    The second road, Skyline Blvd., is less built up, and the views are even better.  The third road, Redwood Rd. is the antithesis of Grizzly Peak Blvd.—a sublime, solitary, and thoroughly unexpected ride through the bowels of a primaeval forest (hence the name).  You’ll expect to see Ents.  And finally the fourth road, Claremont Ave., is a Best-of-the-Best, breath-taking plummet which also figures in our Tunnel Road/Claremont Ave. Loop.

(To see an interactive version of the map/elevation profile, click on the ride name, upper left, wait for the new map to load, then click on the “full screen” icon, upper right.)

https://ridewithgps.com/routes/37929927

Navigation on this route is moderately complicated—you’ll want a map the first time.  Begin where Spruce St. and Grizzly Peak Blvd. intersect and ride south up GPB.  The road is almost entirely up for a long time.  Take the time to enjoy the architecture and horticulture you’re passing.  Each house and yard is a unique work of art.  As you gain elevation, the views of the Bay to your right get better and better and the land becomes less built up.  The best view of the Bay is from a small turn-out on the first curve after you pass Claremont Ave.  The pavement from Centennial Drive (see Adding Miles) to Claremont is brand-new pavement as of 12/2013 and it’s dreamy.

When Grizzly Peak Blvd. T’s loosely into Skyline Blvd., take Skyline to the L.  At the next (very noticeable) four-way intersection, you’ll see Pinehurst dropping down and out of sight at about 10 o-clock while Skyline angles to the right and continues on.  You can take Skyline or Pinehurst.  Whichever road you take, you’ll come back to this point on the other.  Take Pinehurst if you want a short, steep, very curvy descent and, later, a mild ascent up Redwood Ave.   Continue on Skyline if you want a mild descent down Redwood and, later, a short, steep ascent up Pinehurst.

Oakland, San Francisco, and the Bay Bridge between them, from Grizzly Peak Blvd

We’re going down Pinehurst.  Exercise caution on the descent—the corners are sharp and often gravelly (I once met a crew sweeping the road here and a guy hollered at me, “We’re making it nice for you!” as I rode by—very thoughtful.)   At the bottom of the descent you enter a silent fairy-tale forest of redwoods.  This is the East Bay?  Impossible.  Ride past the Canyon School, which will make you wonder why you had to go to that institutional place you called elementary school instead of here.

When Pinehurst dead-ends on Redwood Ave., take Redwood to the L and continue on the way you’ve been going.  The scenery gets steadily less idyllic, because perfection can’t last, and you climb gently into the outskirts of Castro Valley.  Turn around when you no longer love what you’re riding through (the map goes to the edge of Castro Valley) and return to the intersection of Redwood and Pinehurst.  Go back whichever way you didn’t come out.   Since we came down Pinehurst, continue up Redwood, a straight and unvaried but beautiful climb through lovely woods, to Skyline and follow Skyline (don’t miss the almost-immediate R at the Y and go straight onto Joaquin Miller by mistake) back to Grizzly Peak Blvd.

Retrace your steps along GPB to the prominent intersection with Claremont Ave.  If you don’t want to explore (or you don’t want to add another substantial climb to the ride), just ride through the intersection and stay on GPB back to your car.  If you’re up for an adventure, at the intersection go L onto Claremont, a 2-mile curvy, blisteringly fast, hang-on-to-your-hat-exhilarating 10% plummet that is 1/3 of our Tunnel Road/Claremont Ave. Loop.  See that ride for a detailed description.

At the bottom of Claremont, our route ends, because the great riding ends.  You’ll need to find your way back to your car via Berkeley surface streets, and there is no one right way to do this.  Unless you know Berkeley, you’ll want to have a map to consult repeatedly.  The standard route from central Berkeley to Grizzly Peak Blvd is up Spruce—for a more challenging and rewarding route, try Euclid paralleling it just to the east.  Berkeley has a network of “bike boulevards,” where cars are discouraged and you can ride with confidence—try to map out a route that uses them.  Riding through or above (east of) the UC campus is a bit more work but rewarding.  If riding through a busy city isn’t your bag, below in Adding Miles I’ll show you a lovely climb that takes you from the bottom of Claremont back up to Grizzly Peak Blvd.

There are bathrooms and water at Sibley Volcanic Regional Preserve, on Skyline 100 feet south of the Skyline/Grizzly Peak Blvd intersection.

Shortening the route: Ride the stretch along Grizzly Peak and Skyline starting from the Grizzly Peak/Claremont intersection (for the views); or ride Pinehurst and Redwood (for the woods).

Adding miles: The Greater Berkeley area has a plethora of good cycling roads, so you’re close to good riding in all directions on this route.  Here are five options:

1. At the turn-around point in this ride, you’re a short, urban ride through Castro Valley from the Palomares Road ride.

2. At the start of the ride you’re also at the starting point for our Wildcat Canyon Road/Happy Valley Road/Nimitz Way ride.

3. For a couple of miles our route overlaps the route of the Tunnel Road/Claremont Ave. loop.

SF Bay and the Golden Gate Bridge from Nimitz Way (click to enlarge)

4. What you would never think to do, but what I strongly encourage you to do, is putter around the twisty, quirky streets just below where you started the ride, at Spruce St. and Grizzly Peak Blvd.  This isn’t so much about riding as it is about experiencing the Berkeley Hills.  This is a place as beautiful and as culturally rich as Venice or Montmartre.  Each house is a faery cottage, each tiny front yard is a horticultural jewel, and they’re all different.  If it wasn’t “just a Berkeley neighborhood,” it would be a world-class tourist destination with hourly bus tours full of people speaking foreign languages and snapping photos.  It helps to have a good map for this exploration.  The north/south streets are fairly level, the east/west streets can be quite steep.  Stay off Marin Ave., unless, as they say in Rambo 2, “you wish to test yourself”—it’s one of the steepest city streets in America.  Any street that wriggles and that lies west of Grizzly Peak, north of Cedar, and east of Martin Luther King Jr. Way/The Alemeda/Colusa Ave. is fair game.  The shorter and crookeder the better.  I particularly like Yosemite St. and Mendocino St., and be sure to make a stop at Indian Rock Park to climb on the eponymous rock.

5. A user of Bestrides wrote in to ask, Why didn’t I discuss the leg of the SF Bay Trail that goes along the Berkeley/Emeryville waterfront?   The answer is, to me it’s always been a recovery ride so I never think about how sweet it is.  It’s a dead flat, effortless (unless the wind is blowing) cruise along the waterline of the Bay at eye level.  Most of the time you have Hwy 80 on your elbow, but on the other side the views are unique and grand.  You’ll have a lot of company, and pedestrian dodging is just part of the experience.

The Bay Bridge and the SF skyline from Yerba Buena Island

The Trail loops the entire Bay, so you can ride as far as you like, but the plum leg is Marina Bay marina in Richmond to the Bay Bridge and out the pedestrian/bike path on the bridge itself to Yerba Buena Island and Treasure Island.  You can now ride across Yerba Buena and around Treasure.  Treasure Island itself isn’t great riding (Treasure being dead flat Bay fill full of military base architecture and construction), but the views are spectacular—don’t miss the bike path around the north end of Treasure.  You also get an iconic view of the Bay Bridge from directly overhead as the Yerba Buena road crosses over.  The interesting venues between Marina Bay and the Bridge are too numerous to mention, but my favorite is the UC Sailing Club’s operation on the south side of the Berkeley Yacht Harbor, where small-craft sailors practice their skills.