Riding Tandem in San Rafael, Mill Valley, and the San Francisco Area

Biking is an amazing medium for learning about landscapes, people, and culture in a closer, more intimate way, and while unique experiences happen on every bike trip, Trish and my Tandem bike trip was chock full of first time happenings for both of us, despite our ever-increasing checklist of multiday trips: it was the first time we’ve had a homeless man ask if either of us ‘have ever experienced a good ol’ fashion ass-whoopin’’ (pardon my language… he said it, not me); it was the first time we’ve ever had a major mechanical error together on a tour; and it was the first time we’ve ever seen so many other bikers in one place.

I personally had some firsts of my own as well. It was the first time I have ever gotten a tick – they’re really gross by the way; it was the first time I’ve ever flipped over my handlebars on a bike; and it was the first time I’ve ever fallen off a ridge (same experience as the handlebar thing).

All these firsts, both the good and the bad, reminded us how lucky we are to be young, healthy, and full of a desire to experience new things. Our tandem bike trip in San Rafael, Mill Valley, and the surrounding area was definitely an unforgettable experience.


The early morning pack job.


With Trish’s road bike crammed in the back seat.


I don’t think a Toyota Echo is made to have this kind of weight in the back, but it did just fine.


We’re not in the Willamette Valley anymore. Wine making is much more of an industry in central California than it is where we’re from in Salem.

It just so happens that my Spring Break for teaching and graduate school break both align perfectly at the end of March, and Trish and I decided it would be the perfect opportunity to pack up some bikes and drive 10 hours south of Salem to San Rafael, California, a biking mecca right next to San Francisco. Trish actually found out about this riding haven and booked us two nights with a Warm Showers host and two nights with a VRBO host. While all of these bookings didn’t pan out exactly as planned, both hosts, Steve Cherry with Warm Showers and Todd Greenberg with VRBO, were absolutely awesome. But let me back up a bit.

If you’ve never used Warm Showers and are a biker, check it out some time. It’s a site that shows different people who are willing to host bikers in their homes for free in various places across the United States and Canada. Some of the places have extra rooms for use while others have tent space, but they allow bikers to use their showers and often many of their facilities as well. VRBO stands for Vacation Rental By Owner, and is a great way to find alternative lodging to hotels and meet great people along the way. Trish and I have never been disappointed with any of our hosts through either site, partly because you can always see reviews of each host to see whether they’re worth staying with in the first place, which we always do.

A sidenote before I continue: San Rafael and Mill Valley are two of the craziest bike-friendly areas I’ve ever ridden. Both are brimming with road and mountain riders, and the cars in the area are incredibly cognizant and patient with the plethora of riders that clog the streets. And these bikers are Svelte! They have to be because San Rafael and Mill Valley are littered with incredibly steep and long ridges that cannot be avoided. Trish and I experienced these steep climbs and treacherous descents numerous times throughout our riding in the area.

Anyhow, our first two nights we stayed with Steve Cherry, a retired math teacher and avid cyclist.  Steve lives a very minimalist lifestyle, renting out the majority of his home and living in a small bottom floor space with very intentional simplicity. Some of his passions include water conservation, lack of carbon footprint, and most of all, biking.


Steve and I about to embark on an epic mountain bike adventure.


Our tent space in the back of Steve’s yard.


His yard was small but had a beautiful view of some of the ridges in San Rafael.

Trish and my first day of riding was spent biking up to the Headlands Center of the Arts, at the top of the Headlands (just outside of San Francisco), where we met one of Trish and my good friends, Vanessa Kauffman, at her work. We also met her partner, Justice, who biked up to the center with us. The ride was beautiful and highlighted some of the incredible vistas of San Francisco and the surrounding area.


Heading out to the Headlands, we traversed through the San Rafael downtown and found multiple bike paths, a refreshing oasis from the busy streets.  Trish and I find that people LOVE seeing us ride on the tandem.  Other bikers smile and wave, and even drivers look at us and smile.  It is also a great conversation starter at stop lights with fellow bikers.


Heading up to the Headlands, with the Golden Gate Bridge in the background.


I’ve never experienced anything like this road. For those of you fellow tandem riders: don’t ride down an 18% grade hill. It’s terrifying.


Beach spot in the Headlands.

Trish and I split up on the second day of riding. She did a road ride around much of San Rafael while I went on the most intense mountain bike ride of my life with Steve Cherry, who professionally raced both road and mountain bikes in his younger years. He took me to a bunch of unmarked trails on San Pedro ridge, and it was quickly apparent that I was a bit outmatched in terms of technical skills. I found myself riding with reckless abandon simply in an attempt to keep up with Steve as he rocketed down the narrowest singletrack I’ve ever ridden, with a ridge drop-off on one side the entire way. In my attempts to keep up with Steve at one point, my back wheel slipped in some loose dirt on one of the narrower sections of the trail, and before I knew what had truly transpired, I found myself turned 90n degrees and heading straight down the ridge and off the trail. I quickly was thrown over my handlebars and looked up in time to watch my two water bottles slingshot out of their cages as my bike somersaulted down the ridge about 30 feet below me. Other than some scratches, I was fine, and amazingly, so was my bike. The hardest part of the whole situation was retrieving my two water bottles which had been thrown further down the ridge than my bike. Other than this little adventure, I fell one other time, but it was a slow-rolling fall on a switchback, which hurt my pride more than it hurt my body. Still, this ride would end up being the highlight of my rides in the San Rafael area.


Steve and I decided to test each others’ bikes out on the road a bit before switching back to our preferred steeds on the trail.


Views quickly began popping up as we traversed up, up, and up San Pedro Ridge.


The trails were narrow and left little room for error. This one was wide enough that I felt I could take a picture while riding. Others were less so.



Shoddy bridge.




The ride was almost completely singletrack, but even the fire roads were fun to ride.


More views.







A bit different styles of riding, but both worked great on the trail.


This trail never ceased to inspire.


San Pedro is the ridge on the right.

Our final day of riding ended rather abruptly. We had planned on doing a 55 mile ride from Mill Valley to Port Reyes and then Stinson Beach. At this point, we had stayed our first night with Todd, a real estate agent and incredible conversationalist to boot. Although both of us were feeling strong, 10 miles into the ride our chain began missing the cog teeth and we had to quickly unclip before falling over on a particularly steep pass we were climbing. Upon close inspection, it was clear that something was majorly wrong with our back cogs and hub in general, and after limping three miles back into the nearest town, the bike shop regretfully informed us that the rear hub was completely shot, and that our axle was actually broken. This cut short our dreams of a long and challenging day of riding, and we had to call up a taxi to pick us up and bring us back to our host home in Mill Valley.


One of the hills we traversed early on in the ride. Bikers were in abundance throughout.


More of the hill.

Rather than sticking it out the rest of the day in Mill Valley with Todd, Trish and I decided to pack our things and cut short our stay by one day. We thanked our host, who seemed a bit sad about our early departure, and packed our things, headed for Redding that evening and home the next day.


Our hotel, with the disfigured tandem missing its broken rear wheel.


Consolation prize.

Overall, the ride provided us with a glimpse of what the area has to offer to bikers, and Trish and I both would like to head back to San Rafael and ride the area more extensively another time. But alas, Spring Break has come and gone and we’ll have to wait for another long work break before thoughts of our return can begin to percolate.

Categories: Pedals and Packs

2 replies »

  1. Hi Ben, Great blog. I’m sorry you didn’t get to enjoy your final day of riding. I was thinking about you and looking for you guys that day. Now I know why I never saw you. I loved showing off some of the awesome trails. BTW-I was never a pro. You and Trish were fine guests and you’re welcome here anytime.

    • Thanks Steve. We may well be back in the area some time in the not so distant future. Riding in San Rafael and Mill Valley was a whole different level of enjoyment for Trish and me, partly because of the camaraderie we felt with the numerous fellow bikers in the area. Thanks so much for accommodating us – and I’ll fix the ‘pro’ epithet I gave you.

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