The Joy of Scheming
on hatching a plan to hike around the San Francisco Bay Area
Every adventure is lived three times: once in the scheming, once in the doing, and once in the remembering.
I’m a big fan of the scheming stage, which can be a journey in itself—even if I never embark upon the adventure.
Since October 2022, I’ve been happily scheming my next voyage: a hike around the San Francisco Bay Area in June 2023.
In this post, I’ll explain how the idea found me, what attracts me to it, what worries me, and other considerations tumbling around my head.
[Update: I did the hike!]
Where does an adventure begin? In the mind and in the heart.
For me, an adventure must be a love affair. I need to feel a deep, almost romantic connection toward an idea before investing seriously in the research process. Novelty, uncertainty, and emotion are key, as well as the feeling that I’m attempting something “big,” regardless of duration.
At the same time, I’m risk-averse. I like to know that at least one other person has done the adventure before, had a good time, and left behind some kind of roadmap for me to play with. I’m much more of a remixer than a trailblazer.
Finally, I’ve become increasingly wary of the most popular destinations. In the realm of long-distance walking, these include the John Muir Trail, Appalachian Trail, Annapurna Circuit, and Camino Francés. If I suspect that too many people will be sharing my adventure—especially if they’re doing it for the ‘gram—then the romance is gone. Either I need to approach these destinations differently, take an alternate route, or not go at all.
This is all to say: When I stumbled upon the Bay Area Ridge Trail, I felt like Goldilocks finding her perfect porridge.
Clocking in at 400 miles, the Bay Area Ridge Trail (or “RT”, to avoid confusion with the BART transport system) links together the Bay Area’s many picturesque nature reserves and wild spaces.
The first section was dedicated in 1989, and the intended final length is 550 miles. Because the final route traverses valuable private property in the north bay (wine country) and south bay (Silicon Valley), it remains incomplete, and it may stay that way for quite a while.
Maintained by a small non-profit and heavily used by day hikers, the RT has plenty of “beta”—maps, guides, reports—but is not yet a well-known long-distance trail. Bay Area day hikers have seen the blue Bay Area Ridge Trail signs for decades, but almost no one has done the entire trail in one push.
Why? Because the idea is still a bit absurd. You’re not in the wilderness—you’re in the Bay Area! Don’t you have to walk through cities? How will you resupply? How will you camp? Aren’t those campgrounds reserved months ahead of time?
Thus begins the romance.
I feel drawn to hiking the Bay Area Ridge Trail precisely because the trail is incomplete, complicated by private property, and cuts through a densely populated urban area. Where else can you find this combination of factors, or this kind of challenge?
When I imagine myself strolling through downtown San Francisco or ducking under Interstate 580 with nothing more than a backpack, trekking poles, and running shorts… I get excited.
Some unique personal factors up the romance level, too. I spent big parts of my childhood in the north bay, four years of college in the east bay, and have hiked many trails in the peninsula—which means I’ll get to revisit many old haunts. I’ve got friends scattered across the Bay with whom I’d love to crash and reconnect. And as I recently realized, one of my biggest role models in young adulthood—Jack Kerouac’s rendering of Gary Snyder—was very much a wilderness guy in the urban jungle.
Lastly, I actually appreciate the mixed urban/wilderness on the RT, because that means I’ll have more opportunity for socializing. Loneliness was the toughest part of my quickly aborted Pacific Crest Trail attempt at age 22, and it continues to be a challenge on all my solo outdoor adventures. That’s a big reason why I’ve come to enjoy cycle touring—it keeps me more in touch with the social world.
I currently don’t have any friends with the desire + ability to join me on this 3+ week adventure, so I’m going it alone. But that’s fine, because I’ll constantly be passing by friends’ places, convincing friends to join me for short stretches, and meeting tons of nice strangers on trail (as I did on the Tahoe Rim Trail).
For all these reasons, I’ve fallen in love with the idea of thru-hiking the Bay Area Ridge Trail. But what about the logistics? Is it really doable? Thus began the next stage of scheming.
First things first: Who’s done this before, and what route did they take?
On the Ridge Trail’s circumnavigation page, I began to see that while many people have completed the RT in sections, only a few have attempted a continuous hike, and even fewer have completed it. For example, one young hiker started with the intention to thru-hike, used rideshare apps and buses to hop the gaps, and ultimately ended up section-hiking.
I emailed the non-profit to inquire about previous thru-hikers. One of their representatives kindly connected me to KK Fischer, an ultrarunner who completed the entire trail in a week and shared her GPS tracks with me. Very helpful!
Google led me to a handy Caltopo map, which I combined with the non-profit’s official map to realize that… no one really knows what constitutes a “thru-hike” of the Bay Area Ridge Trail!
The whole trail is so broken into bits and pieces, it really seems to be up to individuals to determine which sections to tackle, how to connect them, what’s worth the time, and what’s not. In other words… perfect! A clear license to hike your own hike. (Not that I needed one in the first place.)
Now to decide: Which route should I take? How far should I hike?
After a few hours of messing around on Caltopo, figuring out how I might piece together disconnected RT sections via road-walking and private property crossings of dubious legality, I ultimately decided to only attempt the most established routes in Marin, the east bay, south bay, and the peninsula.
Sonoma and Napa are awesome, but the RT is just too incomplete up there. I would also be worried about high daytime temperatures, inaccessible private lands, and long road walks. So I’ll stick to the core Ridge Trail, designated in red below.
How long will this take? The total mileage of the red line is 318 miles. I’ll need to skip a section in the north bay (between the Highway 37/121 junction to Vallejo) where there’s no safe pedestrian access.
Removing those 11 miles leaves 307. But I’ll also be detouring to visit friends, buy groceries, access campsites, follow bunny rabbits, and who knows what else. So let’s say I’ll actually hike ~320 miles.
Divide that by 20 miles/day (a reliable average for me), and we have 16 days. Throw in five “zero days” for rest + friends, and we have 21 days.
I happen to have 3-4 weeks to dedicate to this adventure, from June 8 - July 8, 2023. That leaves me with a healthy buffer in case I want to take a side-trip, or hang out with cool people I meet, or spend a whole day eating Double Stuf Oreos in my tent. (Which of those is most likely? Who knows… 🤤)
Now I have a route and a timeframe.
Next up: Food, water, transport, and sleeping.
Food: Easy. There are grocery stores and convenience stores everywhere. I’ll need to detour to reach them, but I’m confident I’ll be able to stock up frequently, and I don’t anticipate needing to carry more than two days worth of food. For camping dinners, I’ll take an ultralight stove and cookpot. One trip to REI should suffice to resupply my cooking fuel.
Water: A possible concern. On the high ridgelines of the peninsula and east bay, I may not encounter a water spigot or stream for a long time. I’ll need to bring plenty of water-carrying capacity and be prepared to purify stream water (with iodine tablets) or ask nearby homeowners to use their taps.
Transport: To visit friends or distant resupply spots, I’ll either ask friends to drive me, take public transport, or use a rideshare app (💸). I anticipate having cell phone service almost everywhere.
Sleeping: Tricky! Here’s my plan.
Whenever I’m near a friend’s place, I’ll attempt to stay with them. Or cool friends of friends... maybe you know someone, dear reader?1
If I can arrange a Couchsurfing host, I’ll do that. (To be clear: I really like beds, showers, toilets, and electricity!)
If I’m camping, my first option will be to find a legit campsite that I can reserve.
If the campsite where I want to stay is totally booked (quite likely), then I’ll go there anyway and see if I can join a group that’s already there. (I did this successfully on my bike trip in Montana this summer, in a crowded campsite outside of Yellowstone. Because most campsites allow for large groups with multiple tents, if I can just befriend one small group, I’m set!)
Finally, if all else fails, I’ll stealth camp. This means: I’ll pick an out-of-the-way site, camp when the sun goes down, and leave when the sun comes up, without a trace.
Stealth camping is a time-honored tradition among thru-hikers. In other parts of the world, it’s called “wild camping,” and it’s totally legal. In the United States, it’s… well… yeah. It’s what you sometimes must do to complete a long, non-traditional hike. Performed with care and respect, it doesn’t harm a soul.
Could stealth camping get me in trouble? Yes. Could I manage that trouble? Probably. Do I have enough experience to avoid the worst trouble? I think so. Is there another way to tackle this challenge without massive detours and expensive accommodation + rideshares? Not that I’m aware of. So, there you go. A little exciting, a little anxiety-provoking… just like any real adventure.
That’s it! My scheme to hike around the Bay Area.
It was a delight to write this post, as it was to dream the idea, gather the resources, and weigh the risks and benefits.
While this adventure may certainly evolve between now and June, I already feel like I’ve lived one version of it.
Look forward to the trip report! ☼
But really, get in touch: yourstruly@blakeboles.com
I'm in Oakland, I love your plan and ambition, and if the timing works out I'd be interested in joining you for a portion of your hike and/or assisting a resupply. I'm a mapper and hiking-logistic planner too, and have been daydreaming about doing the East Bay Skyline Trail in one day for a while. I know the East Bay segments really well and can help with any beta you're stuck on. Hope you can make this happen!