The Mid-Aughts Millennial Urge to Build a Cabin in the Woods

Around 2014 we were desiring more. Our third-story San Francisco apartment was an increasingly poor lifestyle fit. Small projects had evolved from arts and crafts to hammering that threatened neighbor relations. We took a stab at a rooftop garden, but it lasted all of a week before our liability-minded landlord demanded it dismantled. We’d hosted some workshops and events for friends (even butchered a whole pig in the apartment) and attended others’ as well. All of this was further stoking our desires for impactful experiences. But we needed more quality time and more space.

To scratch the itch we rented cabins over long weekends. And there were the frequent camping trips, or the occasional lengthy stay at a friend’s family property. But these were piecemeal solutions...if only that Airbnbs frowned on tree house construction. What we really craved was a place we could shape—ideally in the woods. We yearned to spend days together, charting our time tinkering and playing. We wanted to bond over problem solving and projects. And Molly deeply longed to plant a fig tree.

So we thought about moving. Someplace where acreage or even an ample yard could be had. We toured some far-flung options, but ultimately circled back around to the reality that so much of our day-to-day happiness was owed to our local community. We liked San Francisco. We loved California. Moving outside Boise would provide plenty of affordable space and some notable nature, but little else. So we resolved that we weren’t leaving any time soon… but then what?

We pivoted to searching for some kind of weekend getaway to purchase. There were all sorts of properties within a few hours drive. Empty lots, vacation homes, dilapidated cabins. All required major concessions or major money, but we reasoned that splitting the cost with friends could make the math work. 

Conversations about some sort of communal thing had been mounting. A romantic refrain among similarly-minded friends was a collection of small cabins scattered across a large plot, but we talked through a variety of options as they came across everyone’s real estate radar and one dreamy vision would flow into the next. 

I saw a version of this at Beaver Brook, a communal getaway a few hours outside of New York City, while taking a timber framing workshop there in the fall of 2015. In some ways the version—the cabin I slept in graces the cover of Cabin Porn, a book that hits all the inspirational notes for those romanticizing the woods from their city apartments. When I asked Zach Klein [Ed Note: a former Dwell CEO], for advice on pursuing something similar (Zach and his wife, Courtney, owned the property and shared it with a dozen or two of their friends) Zach cautioned that, despite seemingly earnest desires, he had found it difficult to get everybody moving in a singular direction at the same time.

Those words resonated. At that time in our lives with few friends buying homes, throwing down cash on any kind of real estate was a larger financial commitment than anyone had seen. Sure, a number of friends had shown interest—our friend Charlie had even written up a founding document with a cover photo of a tree house drawn onto some woodland real estate we’d recently toured. But getting everyone—anyone—to pull the trigger at the same time was a hurdle. We hadn’t made meaningful headway on any of the properties we’d mulled over, or with the friends we’d had substantive conversations with. Lots of talk, little action.

Zach offered two bits of advice. To make a venture like this real, it takes one person to step up and spend the money, and then offer their friends the opportunity to opt in and share. Second, he strongly recommended buying a home, even if it was a teardown. Getting a loan on a house would be far easier than a loan on raw land. It would already have utilities, and the hurdles for renovations would be greatly reduced from the onerous start-from-scratch model of a vacant lot.

Over the next year we took the first bit of advice to heart and settled into the idea that buying property would likely be a solo venture. But that meant our entry had to be cheap, so for better or worse, we ignored the second bit and opted to search for undeveloped land and build from the ground up.

In late 2016, after checking out dozens of properties up and down the California coast and into the Sierra Nevada Mountains, we were shown a ten-acre parcel at the end of a rowdy dirt road. It was less than two hours south of San Francisco, in the Santa Cruz Mountains—home of California’s first state park, grizzly bears a century removed, and many banana slugs today.

The rutted and steep drive into the property required a running start in our two-wheel drive Honda. Once the road crested there was only a single scrape of flat ground about the size of a U-Haul truck, occupied by a tarp and plywood drying-shed for a small weed grow. Higher above, the realtor bushwhacked us to a tiny sliver of south-facing ridge where, if you stood in juuust the right spot, you could peer through the redwood, fir, oak, and madrone and barely make out the potential of a view. This was billed as a possible building site for a shed-sized cabin, but we were all clinging to branches and slipping off the hillside as we had this conversation, so it was hard to envision just how feasible that was. Still...it was something.

Of the ten acres for sale, only about two of them were semi-accessible via the drive that cut to the upper bounds of the property. That path wove around redwood groves that dotted the parcel—all secondary growth from logging in the late 1800s. Ancient stumps, and a few larger malformed trees that had been passed over during milling, were still blackened like stone from the last wildfire a hundred years back.

The woods were thick, owing to that century without fire and the boon of wet seasons. In the summer the Santa Cruz Mountains can dry out to occasional hundred degree days that nearly beg for a blaze to spark up. But in the winter the hills get about fifty inches of rain—more than Seattle sees in a year. We couldn’t know it standing there, straining for our theoretical-view from our barely-a-cabin-site, but that upcoming winter would be one for the record books… a hundred inches packed into a single season. Creeks would spring up, trees would fall, land would slide, and roads would close for years. We didn’t intimately understand those risks at that moment—we didn’t intimately understand anything—but we did recognize that the region gets no snow and temperatures rarely drop to freezing. So even with the occasionally hot summers and rainy winters, the fairly temperate climate would make our time there—and any building projects—all the more manageable.

We spent a few hours exploring the property and its possibilities, dodging poison oak and sliding down gullies through a carpet of redwood duff and tanoak leaves, trying to locate each boundary flag. There were bits of track and sign from the animals occupying the hills. Our game cameras would eventually establish the larger critters as mostly bobcats and foxes, with the occasional deer and turkey passing through, and even a few mountain lions. But the odds of seeing any of these through the undergrowth of fern, lilac and French broom was slim. California newts and western fence lizards, however, were abundant. You could really hang your hat on those newts...

The land had no power and no water, but an easement could be secured to bring water from a neighboring property. That felt crucial—generators and batteries seemed easy to tote, but any water beyond a few gallons for drinking would be prohibitively heavy. The asking price was all the cash we had, plus another thirty-five thousand we didn’t. But it was a reasonable drive from our apartment, in a region we already enjoyed on motorcycle rides. It was private and wild and abutted even more wilds, yet fairly close to services and civilization. With the tucked-away do-what-you-please freedom, the romance of the redwoods, and the potable water, it was a property that felt compelling. More than any other we’d looked at.

After a couple more visits to poke around and a few weeks of asking probably-too-many questions, we finally decided to make an offer. Getting a loan wasn’t possible. Lenders generally aren’t interested in backing land purchases unless you’ve got a business plan to match it. So we bid the asking price, proposing to pay a majority in cash while seller-financing the remaining balance over the next five years. Then we nervously waited.

When our offer came back as accepted we weren’t quite excited. Not in the way one might expect. Mostly we were filled with uncertainty. Even at a tenth the cost of a home it was the most expensive purchase we’d ever made and felt like a huge gamble—especially for an undeveloped patch of dirt and a handful of newts. There was no clear vision. No obvious Hell yes. A little thrilling for sure. But mostly a nervous Fuck, now what?

The one thing that was clear was the small size of our experiment. Per Zach’s advice, we’d abandoned pooling cash with friends, but this meant buying at the scale we could afford and reducing the scope of aspirations. We weren’t poised to break off parcels or offer our friends the opportunity to build their own cabins (we could barely see a spot to build ours). This property was destined to be more of an experimental entry point than some grand communal living solution. But, from day one we wanted to make it clear that this was still intended to be a community asset, freely available for friends to use, and something we hoped we could all collaborate on.

As we announced the purchase to friends, it was often phrased as "We bought dirt"— wording that betrayed how little of a plan we had. We saw the place as a means to satisfy our desires for projects in the woods. A campsite, and an adventure in rural property ownership that would permit us to remain in the city and maintain a close connection to our social network. We viewed it as a play-space. A canvas. And that outlook remained shockingly consistent over the years.

So, as time ticked by and various structures and gatherings took shape, our plot never took on a formal name. No one would say I’m going to Newt Ranch or even to The Cabin. The property wasn’t referred to by its features or roads or nearby peaks or streams. Everyone just called it The Land.

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Editor’s Note: This excerpt has been lightly edited for clarity.

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Related Reading:

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