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From the Campanile, ride campus paths to Hearst and Oxford. Take Oxford north to Rose; turn left on Rose and right on Shattuck. Just before the tunnel to Solano, turn right on Del Norte; there's a short climb to the Marin Circle. Marin is the second street on the right (the steep climb).
Marin is simply ridiculous; one advantage of doing it first is that all the rest of the hills will look easy by comparison. The main disadvantage is that it could kill you before you get a chance at any of the other hills. I plan to ride it as slowly as I possibly can, and I recommend you do as well. It crosses a number of quiet streets, which people often use as an opportunity to rest without getting off the bike; just turn down the side street and coast for a while as your heart rate comes back under your anaerobic threshold.
The first block is rather steep, perhaps a 14% grade. After that it eases up for 3 blocks, hanging at around 10% until the block before Spruce. That block is again above 15%, and it looks a little like it might be the road's peak--it's so steep you can't see the road above it.
Of course, it's not the peak. Crossing Spruce gives you a little break (remember to take advantage of CVC 57492.1: "the right-of-way must be yielded to people in extreme pain"), and then the next couple blocks again aren't quite so bad. Then the block before Euclid is pretty nasty, pushing 20% grade, but really it's just letting you know that you're about to begin the hard part.
Past Euclid is where the road gets really absurd. The average grade from Euclid to Grizzly Peak is 22%, but that includes the flat intersections. Actual riding is closer to 25%, and that first block is probably near 30%. I don't care how low your gears are, or how light your bike is; either you have the leg strength and aerobic capacity to ride up this hill, or you don't. Good friggin' luck.
The first block, as mentioned, is the steepest. The second block is a little less steep but still ridiculous. The final block is about the same as the second, but it's also much longer than the other two. I always feel tempted, if I have anything left in my legs, to power up the last few meters just to get the damn thing overwith; I recommend against doing that, because we have a lot more climbing to do today.
I also recommend not stopping right at the top of the hill; turn left and coast down Grizzly Peak for a while, and try to keep your legs moving a little so you don't cramp up. Take Grizzly Peak down to where it intersects with Spruce and Wildcat Canyon; turn right on Wildcat Canyon. There are a few good places to turn out and rest there.
Take Wildcat Canyon about 3km, past the Brazil Building; South Park Boulevard will be on your right after a short downhill.
Mild Discomfort Climb 1
Spruce Street, from Hearst to Grizzly Peak
Take campus paths to Hearst and Spruce. Spruce is a fairly gentle climb, averaging a little over 4%, up to the intersection of Grizzly Peak and Wildcat Canyon (about 6km). If you plan to ride Death Climb 2, go straight across Grizzly Peak; if you want to take Mild Discomfort Climb 2, turn right on Grizzly Peak.
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South Park is the fastest descent in the East Bay (with the possible exception of Moeser for those with death wishes); the top part has curves but isn't twisty enough to slow you down, and then you can blast out of the last turn into the steepest part of the descent, a straightaway near a parking lot. I hit 88.5kph once (my fastest recorded speed anywhere). Today, though, we are going up it.
South Park is actually probably the easiest of the five climbs. It starts out fairly easily, then gets rather steep around the end of the straightaway. It continues steeply basically until the top of the hill, but with only 200 meters total climb, and grades which will look easy after Marin, it shouldn't be that difficult.
South Park ends at Grizzly Peak near the steam trains; turn right and descend on Grizzly Peak to Shasta (about 3km) and turn left on Shasta. Take Shasta down to La Loma; there are a number of turns on the way down; just keep choosing the direction that doesn't have a "No Outlet" sign. Take La Loma across Hearst, where it becomes Gayley.
Gayley takes you by the east side of campus and past the Greek Theatre. Turn left just before you reach Kleeberger Field and Memorial Stadium.
Mild Discomfort Climb 2
Grizzly Peak, from Spruce (or Marin) to South Park
Grizzly Peak is a pleasant road which climbs gently towards the top of the hill. It's about 7km to the intersection with South Park Boulevard, just past the highest point on the road. When you get there, turn around; we're going back to Shasta (follow route above back to Shasta and down).
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Centennial is the road most frequently used by strong cyclists to get out of Berkeley. It starts fairly gently, then starts to climb steeply near the Botanical Garden and past LBL. It's a fairly constant 11% grade from the LBL gate to the rest point at Lawrence Hall of Science. There, it flattens out for a while, and then climbs a little more, less steeply, to reach Grizzly Peak.
Go straight across Grizzly Peak onto Golf Course Drive. This descends sharply for a while, then has a short climb and a further descent to Wildcat Canyon (keep to the right at the forks in the road). Take Wildcat Canyon about 2km to Inspiration Point, then descend to the stoplight at San Pablo Dam Road/Camino Pablo. Turn right on Camino Pablo. Take Camino Pablo about 3km to El Toyonal, the last light before entering Orinda; turn right on El Toyonal.
Euclid, from Hearst to Grizzly Peak to Golf Course Drive When you get to the bottom of Euclid, turn around and head right back up (if you're looking for even milder discomfort, you can hang out at the top and eat blackberries or something). Euclid is similar to Spruce, but slightly steeper in parts (the block before Marin is a tough one). When it ends at Grizzly Peak, turn right. Take Grizzly Peak about 3km to where it intersects with Centennial and Golf Course Drive. Turn left on Golf Course drive, then follow the instructions above.
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El Toyonal is a pretty rough climb, about as steep and long as the hard part of Centennial. But then the hard part starts. You can continue on El Toyonal and go over a partially washed-out bridge and hook up with Wildcat Canyon, but we're turning left and going up Lomas Cantadas, which is the hardest climb to Grizzly Peak from the east. It has about three switchbacks where you're already working pretty hard, and you see the hill getting steeper into the switchback, but then instead of easing off it actually gets steeper on the next straightaway. The straight climb towards the stables is the hardest part; once you make the right turn past the stables towards the llama pen, you have pretty much made it.
After the top of the hill, the road flattens and descends a little to Grizzly Peak by the steam trains. Turn left on Grizzly Peak and take it about 6km to where it ends at Skyline/Tunnel. Turn right on Tunnel and take it 6km; turn right at the stop sign and continue descending past the Claremont Hotel. Turn right at your first opportunity after the hotel; that's Claremont Boulevard.
Mild Discomfort Climb 4
Wildcat Canyon to Grizzly Peak
When you get to the bottom of Wildcat Canyon, go back up. Wildcat Canyon is a varied, woodied climb, with pitches up to about 9%, and a lot of longer, slight grades. After you pass Inspiration point and the Brazil Building, it descends slightly to Grizzly Peak. Cross over Grizzly Peak to Spruce; take Spruce down to Hearst and turn right, then left on Oxford. Take Oxford about 3km south to Ashby (it's called Fulton at this point); turn left on Ashby and take it up to where it intersects Claremont, then turn left, or go straight for Mild Discomfort Climb 5.
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Claremont is the least steep of all the hills we're climbing today, but it's harder than Centennial or South Park because it's longer. Unlike most of today's climbs, it comes at you in waves; there are sections which are well above 10%, particularly the first of two switchbacks near the top. There are pitches which are less steep, but really nowhere you can get a rest until after the last switchback.
Turn left on Grizzly Peak at the top of Claremont. This continues to
climb, but less steeply, to the top of the hill. Turn right after
about 4km on Lomas Cantadas, then turn left onto South Park Drive, and
bear right onto a small footpath with a gate across it. We'll have to
dismount to get around the gate. This footpath climbs fairly steeply
for a while, then flattens out. Keep bearing to the left; at one
point there's a fire trail to the right and a barely-paved path to the
left, stay to the left again. After that fork, there's another
switchback and then the final climb begins. It's not very long, but
it's extremely steep (in two pitches) and often covered with pine
needles or gravel. After you're past the second steep pitch, it's
only a short ride to the very top of the hill (Vollmer Peak).
Congratulations!
Mild Discomfort Climb 5
Tunnel Road to Grizzly Peak
Stay on Ashby as it becomes Tunnel and passes the Claremont Hotel. Bear to the left where it exits onto Highway 13, and then make a left turn about half a klick up the road, where Tunnel continues. Tunnel is a fairly steady 5% grade with some nice views. At the top, turn left on Grizzly Peak and take it to Claremont, then follow the directions above to get to the peak.