top of page

Day 63: The Ballad of Wyoming, Part 4 – The Jackson Roll

Here at the outro to our Wyoming moment, we savor the trails around Teton, navigate a high-end tourist town, then figure out where to hunker down as the weather turns.

Day 63 we're up around 5 — one prereq to stealth camping is that you're packed and away before anyone else is up. Not that anyone's around the Jenny Lake Lodge just now (except maybe bears, which is why we hung our food), but better safe than… Oh, and it's just started snowing.

Packing is quick, partially because we slept in most of our clothes. Pretty soon we're on our way again, though our first stop isn't far (or indoors, even though it's friggin cold). We're going to have breakfast and watch whatever sunrise breaks through the clouds from the Jenny Lake Overlook. And the clouds are thick, covering the tops of the near Tetons, but still the scene is epic. And there's only one other masochist out here, with a DSLR and a tripod, who keeps running back to his car to warm up. So it's probably as uncrowded as a spot like this gets. It is a good morning.

We stay until the creeping cold starts making our fingers and toes numb, even with the gloves and toe warmers and multiple socks and everything else we can think of. But when we do set off again, we're greeted with an excellent discovery: there's bike trail all the way from Jenny Lake to Jackson. And all bike trails are a glorious respite from the road-shoulder life we've been leading, but the fact that this path is rimmed with snow, that the cloud-topped mountains linger to our right, and that we can take this trail all the way to Jackson… Our whole short ride today is entirely on a bike path? This is fucking heaven. (The wider Jackson area is known as Jackson Hole — it's still sinking while the Tetons are still rising. Thus our leisurely roll on down into this valley's central hub.)

Sara tamed a tumbleweed.

We pass through a big old expanse of protected ground that we discover is the National Elk Refuge before we t to town — but, sadly, don't spot an elk. (We're told there can be herds of literal hundreds here at times, though!) Our first stop in Jackson is the Bridger-Teton NPS station. The doors are locked, and there's pictures of all the merch stuck to the front windows. We call inside and someone comes out, shows us a few postcards and other things. They end up not having our sizes in the shirt we like, so we're about to just head out with just a sticker for the collection, but as we're leaving the woman brings us two of these — for free! (She thought we were "cute.")


So that's an exciting start. From here, we try to find a coffee shop to sit, regroup, look for a place to stay. We park the bikes, observe that icicles have formed on the bottom of my guitar and on both our seat tubes, then begin to hunt. This is where we start discovering the true nature of the beast that is Jackson Hole, Wyoming.

First off, there's nowhere to just be. Which is a little bit the result of Covid, but the response to Covid here is mixed — the place is still crowded, mask wearing is about 60%, and the first two coffee options we inspect have lines out the door with little regard for distancing. We quickly give up on our idea of a coffee shop and look for a place to sit and have second breakfast — we climbed a mountain pass in the wind yesterday; we deserve a second breakfast. Eventually we find a place where there's no line, where the tables are a little more spread apart. The food is good but expensive, which we realize will be the way here: most things have a certain degree of quality, but nothing's free or even moderately priced. This is a place for the rich.

We find that one of the local hotels has a hostel in its basement, the cheapest bed in town. We book a bed and head that way, but they won't let us check in yet. We wander over to the bike shop, where the people are finally chill — they loan us a pump with a pressure gauge, and help adjust my shifter tension gratis. Thanks, Hoff's Bikesmith.

We get a call that we can check in, so we head to our still-expensive hostel bed. Check-in is weird and they make us leave our bikes on the street. The hostel space is cavernous, but everything is roped off, despite the fact that there's no one else here. We find our slightly-taller-than-waist-high space and cram our bags into a locker. There's no food or drink allowed, so we'll be cast back out to seek our next calories. We don't like complaining, focusing too much on frustrations, but we're not exactly loving Jackson's vibe so far. The whole town is like one of those benches in New York that's designed so you can't rest on it.

Number 9? Number 9? Number 9?

Well, we make the best of it. We go to a "cowboy bar" that's more like the bar in a cowboy-themed casino, but it grants us some space where we're allowed to be upright (and seated astride saddles-as-bar-stools) while we consider our plans for the next few days — there's a nasty-looking cold front pushing through this weekend, and we aren't quite sure what to do. It's supposed to snow heaps and stay well below freezing for days. We look at the weather up in Missoula — it's even colder there, and has been, and looks like it's been snowing. Apparently certain roads in Yellowstone are already closed. This has all been happening, been coming at us in the background for days and days, but we've been focused more on the wind and cold and snow that was already on our heels instead of on the stuff that may or may not be rolling down out of Canada. Well, now Canada's coming for us.

This isn't exactly a surprise, though. And proof of this is the mere fact that we're in Jackson — Jackson's not actually on the TransAm, it's just at the end of a little down-and-back detour that some people take. For us, as the cold closes in, we realize that Jackson is going to be the last place on the official map that we see for a while. Ya'll, we're going rogue. We're skipping Montana and cutting straight across Idaho. We've realized that, if we don't do it this way, we probably won't be able to do it at all.

Well, we drink about this a little while. We finish our one beer each at the cowkid club, then grab a flask-size Jameson and take it back to the "room", stupid rules be damned. And it's around now that a few pleasant events occur: first, we hear back from a Warm Showers host that Sara's reached out to — they live about 50 miles SSW of Jackson, and they're willing to put us up for the next two nights while the storm blows through. Second is that I finally get into touch with a buddy I was in the Peace Corps with, whom I haven't seen since 2011 but who did the TransAm back in 2018. Mike was actually driving from Seattle to Denver while we were in Wyoming, and we'd intended to stop and grab a drink or something, but he passed on the exact day (at the exact hour, in fact) that the wind defeated us and we accepted the ride to Lander. Since then, we've lacked either time or reception, but today we got in touch finally, and talked for a good long while about the last decade of our lives, but more specifically about the TransAm. Mike offered us some real solace, least of which was, "Don't worry — your hands will keep going numb for another month after you stop, but that'll go away eventually." Thank fucking goodness.

In better spirits, we try to take Jackson for what it's worth. First, we walk our bikes over to Hoff's Bikesmith, where they kindly let us stow them for the night. Then we acquiesce to the fine-dining industrial complex: we pick a nice Italian place, accept that it'll be a pricier meal than we're used to, and we have a great early dinner. Then we head back to our room again because I've bought tickets to a concert — a digital concert by The Mountain Goats. And I'm a huge Mountain Goats fan (the first messages between Sara and me, back when we met on a dating app, were about the fact that we'd both been to the same Mountain Goats show in Brooklyn two weeks before we met). I'm a huge Mountain Goats fan but… not an uncritical one. I get really annoyed by the show. (Sara, who also digs the Goats, does, too.) But it turns out that we have a little of the special chocolate left over from Colorado. So we both eat some of that. And then the show ends, and we watch Bake Off. Emphasis on the bake. And we pass the F out.

Day 63: Jenny Lake Lodge to Jackson, WY, 25 miles, 425 (!) feet of climbing, a fantastic non-sunrise, a fantastic bike trail, a fantastic meal, a fantastic route change, a not-so-fantastic town.

All for now.

Recent Posts

See All


bottom of page