A lot has happened since chapter one, a lot of miles have passed. I’m up to 169 miles of IAT since I out and back’ed (o/b’ed) the Brooklyn Wildlife segment on July 16 of this year. I recently revisited that segment when Sara, my sweetheart, was getting the last of the miles she needed for the Mammoth Challenge. She totaled 42 miles and I totaled 72 for the month of October. My original goal was to get 100, but as is the case with some goals, the trying to get there is more important than actually getting there. There’s a life lesson there, and one I’ve been putting some intentionality towards learning as I try and get better at being process and not product orientated.
One process I thoroughly enjoy is the planning that goes into my hikes/backpacking trips. I spend a lot of time creating plans, doing math, coming up with options A through F, talking to Sara and Nic about which segments I’m looking at doing next, falling asleep thinking about packing lists and weather forecasts, ignoring customers to look at the IAT atlas and think about multi day trips to finish Lincoln county. This practice serves at least two purposes: 1 it gives me something to think about/look forward to/pass the time, and 2 it takes all of the thought-work out of adventure time, so when I show up at the trail head I can put my phone on airplane mode, stop thinking, and tune into the trail.
This past Monday, when I set out on the Cross Plains segment with my dear friend D-Rock, he commented on how effortless my careful planning made everything. “It takes all of the anxiety out of the trip and I feel like I can just show up and have fun.” Which is pretty much the point. Perhaps my time guiding has made a lot of those things second nature. In fact, I know it has.
D was a last minute addition to my trip. We had plans to go climb on Sunday, the day before I stepped off, but as those plans fell apart we made new ones for him to join me. “I’ve got everything figured out.” I told him. “I have all your food and weed covered, and likely any gear if you need something. You literally just need to show up and walk,” I told him. “You’re on your own for snacks, though.” He was impressed with the four-screenshot-long master list that covered packing, to do, and itinerary. “That’s only one of my lists for this trip.” I boasted.
The Cross Plains segment is a perfect stretch of trail for a one night trip. From the southern trail head it’s 8.3 miles to the dispersed camping area (DCA) and then .7 miles to the other trail head. And that’s what the plan was: Hike to the DCA, make camp, make a “summit push” to the trail head, then back to camp for the night. Option B was to push on past the norhtern trail head and hike the connecting road to the Table Bluff segment for no other reason than to make a longer contiguous highlighted line in my guide book.
I have the goal of hiking every segment of the IAT in both directions and I track my progress by highlighting segments in my IAT guide book: Yellow for one direction, blue when I hike it in the other direction, and green when I out and back it. It’s a trick I use to keep track of the road trips I took one year in my U.S. road atlas. That first year I used yellow, the next year I used blue, green being the roads I did in twice… and then I began using different colors for subsequent years. And so, one by one I’ve been obsessed with highlighting segments green in my guidebook.
Perhaps I ought to go back and rename this collection of adventures “Chasing the Green Line” or something as the Tolkien reference, a well intended but perhaps misguided homage to my mother, nearly cost me twenty dollars to D-Rock; as it is, I owe him a snaky bar. And that’s fair.
We met up at the parking lot on Old Sauk Pass Rd. at 11. We decided to leave our packs in the car and do a 2.2 mile warm up by heading south to the trail’s terminus and then back to the car to get our packs and finish the trail. I did this when my cousin Mike and I hiked Harrison Hills. Before we hit the trail fully loaded we out and back’ed Alta Junction. A proper stretch and warm up are vital to longevity especially now that I’m in my middle ages. There wasn’t anything remarkable about this part of the trail, that I recall. There are a couple potential boulder problems along the way. They were those random cottage sized sandstone boulders you see in the Driftless region of Wisconsin. Perhaps they are the shaved off tips of spires or towers somewhere up north near Gibraltar Rock, but we did not bother sending them. The day was about hiking, and we were on the move, averaging nearly 3 miles an hour when we took the alternate raised wooden walkway from the spur trail back to our car.
That’s a thing I really like about out and backs. On the way back, I have a chance to hit all the spur trails and see where they go. And so it was that D-Rock and I took the other way back to the parking lot and sang made up songs and tapped our sticks in time over the wooden bridge.
The IAT has some truly incredible wooden walkways and other mobile skills projects. They’re a unique human made touch to the whole experience. I think I love them so much because they serve as a profound link to myself and the community of volunteers that make the IAT a reality. I’m not big on crowds, groups, strangers, or most people in general, but I try and remain grateful at all times while I’m on the trail for the folks that create the opportunity for us.
After a quick snack, we prepared to hit the road… er, trail… my feet feeling good in the Oboz Sawtooths I got at the REI Garage Sale the other day, and my Baltoro 65 riding semi-comfortably on my back. I’d had this pack out a few times, and after a couple shake downs (see Ch. 1) and a couple trips (see upcoming chapters) I’ve got it dialed in, though I’ve been sort of wishing I had gotten a 75 liter. Colder weather requires a thicker sleeping bag and I am all about sleeping in comfort, so I pack a Nemo 15 with a cheap liner and a Switchback mat to put under my Cosmo 3D pad. — the combined R-value of those is 5.2, making it good enough for what I’ve done so far. With my Comfort Plus SI mat in place of my Cosmo, I’ve slept in 26 degrees and was quite comfortable, though I do have dreams of getting a better liner and proper 0 bag so I can get out and do some backpacking this winter. (If you’re wealthy and feeling generous and want to donate, those are a couple things on my wish-list. )
So the funniest thing happens before we even leave the parking lot. My sternum strap broke on the right side, where it connects to the shoulder strap (FYI: I’ve seen a lot of bags in the REI garage sale because this happens. It’s a design flaw: The place where you snap your drinking tube to your sternum strap is the same piece of plastic that clips your sternum strap to your shoulder strap. After X amount of use, it breaks along the spine and comes right off. Gregory will send you a new strap if when this happens to your pack. My advice: Be forward thinking and tell them it broke before it does, that way you’ve got a spare with you if when this happens to you on the trail.
What I did to keep me moving: A trucker hitch out of a piece of para cord. It’s solid, doesn’t slip, and most importantly it’s quick to get untie and retie, so getting in and out of my pack wasn’t an ordeal.

As soon as we got to the road and back on the IAT proper we were quickly confused by a well meaning ranger. He was trying to tell us that over the summer they’d created a new portion of the segment that left the road and takes hikers through a field instead of down a busy highway. Some people are not gifted communicators and after a little frustration and way too many words, D and I pressed on figuring if there was some sort of addition to the trail, we were astute enough to find it. (Given the signage, the presence of the familiar yellow trail blaze, and obvious foot path, we literally could not have missed the turn off unless both of us had tried, or had been looking left for a full quarter mile.)
The new piece of trail takes you through a couple clover fields that I only assume are defunct corn fields, but it’s better than walking down the highway. Once we crossed HWY P the trail took us up a moderately steep wooded hill and along a densely wooded ridge. Peak colors for the fall season have since passed through this region of Wisconsin, but there are still a few true believers out there holding on to their colors for as long as they can as they shiver against the cooling winds.
A couple tight switchbacks and we were on the other side of the hill, crossing a boardwalk, turning right along Black Earth Creek — a body of water in which D’s father had built a notable reputation as a fine fly fisher. D knows a lot about fishing and hunting, so it’s great to listen to him talk about those things as I never have partaken in either. A birder, he also knows quite a bit about birds which I (as a birder) truly appreciate.
D and I are very, very different people. We’ve only hung out once other than climbing together, and after he took a pretty serious ground fall early this season we didn’t see much of each other over the summer. Our differences make for great conversation and forms this sort of Laurel and Hardy, Abbot and Costello sort of relationship. We play a lot off one another and spend a great amount of time making jokes, goofing off, and having plain old fun. We bring out the youth in one another, I feel. Something about adventuring with D-Rock makes me feel like I’m 12.
And I don’t think a pair of unruly 12 year olds would have made much more of a (good natured) commotion than he and I did when we all but rolled over one another to get through the doors of the IATA HQ. We wated hot instant coffee from plastic camp cups, pets from the office dogs, and trail merch. The staff there was gracious, caring, fun, knowledgeable and very sweet to a couple weirdos that were likely a bit more dirtbaggier than most of the customers they get. Though we completely forgot to resupply our water, we did make some coffee, buy some IAT merch, get new hats, and become members of the IATA (doing so included a free stocking cap (which would replace the stocking cap that went missing when Sara and I did Monches)… So D went from having one hat on the trip to three, and I went from three to five.)

Back on the trail we cut through the neighborhood, departing on Lewis St. and began the steep pitch to the top of the hill. This side of the hill, I feel, is what gives the segment a 4 for elevation in the guidebook. It’s a pretty decent little jaunt, and reminded me of the CCC at Devil’s Lake, if the CCC were a steep dirt path that instead of grease coated stairs that are trying to kill you.
We timed our trip absolutely perfect and met the sunset as we passed the first lookout bench we came to and crested the hill through the woods. The sun was lowering behind the hill across the valley and lit the forest orange. The Ice Age provides some genuine beautiful sights, but the sunsets that I’ve seen this fall from various hills on the Trail have been some of the most stunning I’ve ever seen. A combination of the warmer temperatures than usual, and the extraordinarily long change in leaf colors have created some fantastic cloudscapes over breathtaking sunsets. The one I saw with D that night was one of my absolute favorites.

By headlamp, we made camp and ate dinner, then struck out the last .7 miles to the trailhead on Hickory. Like I said, I’m chasing the end of that long green line, so it didn’t take much deliberation for us to choose option B and press on to the Table Bluff segment. Likely due to D’s youthful zeal, I felt great as we sped through the dark streets, discussing in hushed voices the dead battery situation in D-Rock’s blinking red light. I took the rear guard with my Petzl Tikka lighting the way from behind D and my Black Diamond Spot for a blinking red light on the back of my head, while D-Rock got things going on the charger so we could be safer on the way back.
We only hiked to the top of the hill at the south end of Table Bluff. An incredibly fine piece of gear if you can come across one for a good deal like I did, my Garmin Instinct Solar said we had done13.12 miles for the day, I felt we’d found the perfect turn around point as I’m a lover of high irony, and the whole 1312/ACAB thing just couldn’t be ignored. We sent the boulder at the top and agreed that even from a sit start, it went at V-Easy. I’ve retroactively named the problem Goat Yodel and don’t claim a FA, nor did I bother to put it on Mo. Pro.

From the top, D played some music on his pocket synth while I contemplated existence and reveled in the glory of what I’d just accomplished: Cross Plains was the last segment I needed to complete Dane County and earn the Dane Drifters patch that I’ve been gunning for since I found out about it in October. I cannot explain exactly how much and for how many reasons I love the term “drifter”.

And so there I was… a drifter. I had stood atop that rock a few weeks earlier, yet I felt like a profoundly different person that night, and I can’t really explain why. But there had been a shift inside my chest over the few dozen miles between the last time I climbed that boulder and this time, looking down at the moonlit valley and noticing the stream I had somehow forgotten about, or hadn’t originally noticed. What I felt went way beyond feeling accomplished, I felt somehow more legitimate. In the month between, I had ticked off my 100th mile on the IAT, my Mammoth Challenge, and my Dane Drifter challenge all within the same month.
I listend to D and let his song carry my thoughts beyond the recent past to when I was living in Texas and I dreamt of being a backpacker. If I’m not mistaken, I may have wanted to take up backpacking before I wanted to take up climbing. In an ironic twist, it was all of the trips up and down the CCC with a rope and a pack full of gear that got me thinking “you know, I could probably do ok taking up backpacking…” The journey between there and here, between the deserts of west and south texas and this here boulder in Wisco, was best measured in wisdom and experience instead of miles and years. I had become far more competent, capable, confident, and… happy.
That night I discovered something, washed in D’s red light, I realized there was a feeling I’d been living with that I didn’t have a word for. But there it was, somewhere down there in the valley, the knowledge of something I didn’t fully understand yet. But like a rock in my shoe, I knew it was there, and now that I was aware of its existence, I couldn’t stop thinking about it.
D-Rock finished his song, we climbed down, and I called my sweetheart to talk for a few minutes as we started our trek back to camp, walking a long portion of the way with our headlights off.
The next morning we took our time making breakfast and breaking down camp. The hike back was sort of a blur, as it usually is. It was a short 7 miles and we stopped at the IATA HQ to see our old friend Gandalf again and refill our water. We made good speed on the way back, running into a gal I used to work with and her friends.
I told D about my recent trip up north where I nearly took a job at a place that labeled itself a “wilderness therapy center” but was, in fact, nothing more than a scared straight program that used poorly behaved dogs and the wilderness as a form of prison to conduct behavioral modification. Though the establishment claims they do nothing of the sort, I have a piece in the works that details how that place is nothing short of a dumping ground for the (usually) brown or black adopted children (most often from other countries) of rich white folks who are tired of dealing with their “troublesome kids”.
See, me and D both believe that healing is a team sport, that recovering from trauma works better when you’ve got people to work through it with. He and I are very similar in that we both use the outdoors as a form of therapy and a way to process trauma, heal from it, and grow. So, when he and I (and our good buddy Mark) are out climbing together, it can get pretty serious, pretty heavy.
But the bulk of that emotional weight we left up there, on those winds on top of that hill, and by the time we crested and descended the hill across town we were feeling far younger than we were again. At least, I was. D’s younger than me, so I guess he likely feels young by default, but he’s an old old soul. I felt young enough to dance, in fact, and I did. Pantomiming the stage performance of every member in the band as we jammed Radar Love on the bluetooth speaker. D had never heard it, and as it’s one of my all time favorite love songs, I had to make sure it was as memorable an experience as possible. I even did that cool thing where the lead singer jumps in the air, using my hiking stick as a mic stand, and with my Baltoro on my back. How much more sore that performance over our last half mile made me the next day I don’t know, but it was totally worth it. By the end of last night (I had returned the prior afternoon) I was mostly hobbling around in good form and I’m sure that if we were still on the trail and had we taken a long morning to rest, I had another 7-10 miles in me for day three.
But we’ll have to save those miles for another segment, another time. Right now, I’m still slightly recovering, having returned the day before yesterday. I missed an interview today because I was up puking and shitting all night, and then again early this morning. Likely I won’t get that job, and that’s ok. That’s the way she goes, I guess. I’ve been really liking my retail job these days. Being out in public is probably good for me, I can be pretty reclusive. And when my internship ends I’ll likely pick up more hours at the store and use my down time to do some winter hiking/backpacking and write about it.
See, the thing I came to up there on the hill the other night, that rock in my shoe, is something I was talking about with my friend who’s name also happens to be Sarah. So here’s the concept: “What if I’ve been happier than what I was aware of these past few months. Is it possible that I’ve gone so long being so miserable, and due to the fact that until recently I didn’t believe I deserved happiness, that happiness, contentment, fulfillment were all such foreign concepts that I didn’t know what they felt like?” It’s possible, she said.
And I believe it is. I think trauma can break parts of you that make it difficult to impossible to identify, feel, and hang onto positive emotions. Especially if you’ve bought into the lie that you haven’t earned it, don’t deserve it, are too damaged, too dark, to mean, too… whatever. And all of that is a lie, you know. You do deserve love. No matter what.
What I’ve found is that backpacking, hiking, climbing, kayaking, adventuring, those things erode that inability to feel goodness. It’s like, I’ve somehow walked off the callouses that had gronw over emotional nerve endings. The wilderness has worn all that down, taught me to heal, made it impossible to ignore joy and beauty and good feelings. Once I began recognizing what feeling good feels like, it made it easier for me to see, these past few months, hard as fuck though they have been, that holy shit… I’ve been kind of happy. I just didn’t know that all these feelings had a name.
It’s weird, it feels so awkward and makes me feel so alien saying that: that it took me time to realize that what I was feeling was happiness. It was contentment, it was satisfaction and pride and self love, and it’s weird that it took me 40 odd years to really figure out what those feelings feel like. But that’s just how it is, I guess. That’s the way she goes.
And so it was easy to have fun that day, on the way back to the car. It was easy to just walk with my friend, be goofy, be happy, and have fun. as I said to Sara, my sweety, “It was an incredible amount of fun! The quality, amount, and sustained level of that trip is, was and will always be un-fucking-precedented.”
Thanks for coming with, D.

(this is the song that’s supposed to be playing while the credits roll)
https://music.youtube.com/watch?v=g5i6duhB9mk&list=RDAMVMg5i6duhB9mk