I’m 55 years old, been riding seriously since I was, what, 11? And in all that time I’ve never ridden the Mount Hamilton loop. Between 97 & 105 miles depending upon route options, and heads from Livermore (or elsewhere; obviously you can start wherever you wish), over Calaveras and down towards the bay, then up Mount Hamilton, down the other side & finally north on Mines Road. to Livermore.

I’ve ridden up Mount Hamilton many, many times, and sometimes down the back side to the bridge over the creek and then head back up. And I’ve ridden Calaveras and every other piece of this ride at one time or another. I’ve even ridden over Mount Hamilton and on to Livermore, in the Mount Hamilton Road Race, but that was many, many, many years ago. Long enough that I retained dim memories of the backside not being much fun.

Today, Kevin and I decided to test those memories. Besides, as I’ve written before, Kevin likes to try new rides, something that becomes increasingly difficult over time. His first choice was to head to the Sierras and do Sonora Pass, but it’s been busy enough at the shop on Saturdays that I really haven’t felt like a long drive in the dark after work.

We started the ride in Livermore instead of someplace a bit closer because I was concerned about having to continue riding much further after Mines Road. I remembered the main reason I didn’t enjoy the backside- that long run down the valley towards Livermore, punctuated here & there by annoying “junk” climbs (not long enough to really get a rhythm yet incredibly efficient at sapping your strength and making you feel like you’ve spent too much time out in the sun) but, worst of all, steady headwinds that make you fight your way downhill.

The first 25 miles or so went by easily enough, but it did feel a bit weird hitting the base of Mount Hamilton nicely warmed up rather than at the very start of a ride. We stopped at the top for the mandatory coke (remember, crisp $1 bills only, anything soggy from a back pocket won’t work) before heading down the back side.

If you haven’t been down the back (east) side of Mount Hamilton, it’s just like the front (west) side, only a lot steeper. So very bumpy, gravel here & there, and not really a very fun descent. But the climb back up is both challenging and fun, making the descent worthwhile to try someday. But we weren’t coming back up; our car was in Livermore and Mines Road was standing in our way.

The small rises between the bottom on the east side and San Antonio Junction weren’t as bad as I had remembered, but still, by the time we got to the Junction, it felt like we had already put in a tough 100 miles, not 65, and we had another 30 to go. But fueled up with a cookie and coke from the Junction bar, we felt ready to go!

Or not. That last 30 miles was one of the toughest of my life, battling the two remaining (and significant) climbs along with the headwind. Kevin was pretty much cooked by the time we finished the final climb, so it was my job for about 22 miles to just go to the front and fight the wind all the way back to the car. Ouch. The first dozen miles were the worst, because they paint mile markers in huge numbers on the road, and between 22 and 10, it felt pretty discouraging. Somehow I kept it up though, towing Kevin back to the car, both of us more exhausted than anytime in recent memory.

My recommendation? Do this loop if you want a challenge, but if you’re looking for “fun” look someplace else. Or find out what time of year you have tailwinds heading towards Livermore rather than headwinds.