Where we find Sisyphus, the old dog, learning a new trick—and then checks the trick’s math.
Day 1–SisyphusDW7 and SMAP leave Merced in the cool blue of early morning, the San Joaquin Valley still quiet, and within an hour you’re climbing into the Sierra foothills on CA J-59 to CA-108 where the road tilts and coils through oak-studded hills the color of dry wheat. As we climb, the mountain towns— Sonora, Twain Harte, Long Barn, and Strawberry will be filled with summer tourists seeking relief from what will likely be summer’s emerging torridness. Then it’s up and over Sonora Pass down to Bridgeport— unhurried, the kind of place where the hardware store has been open since 1887 and the diner still has a pie case. By the time you drop into the basin and range topography of Nevada passing through Yerrington, at the end of Day 1, you’re already in a different California than most people ever see. New Pine Creek Campground puts you lakeside under the pines, quiet enough to hear the water.

Adventures in AI
That’s how Anthropic’s Claude conceived the first day of what would come to be known as “An Epic Western States Ramble.” This would be on my Moto Guzzi, with SMAP on his Suzuki sometime in mid-June. In the event you don’t know what a Moto Guzzi or a Suzuki are, they are motorcycles and not an Italian/Japanese boy band, Moto Guzzi and the Suzukis. I was impressed by Claude’s idyllic sketch of the first day. But there was something fishy about the day beginning in Merced and ending at the California/Oregon border. That’s a long day…
Though I had dipped a toe in using ChatGPT’s LLM, for planning the Anza-Borrego/Salton Sea ramble last March, this was my first full-on foray into AI planning for a moto ramble. In March, I was still wedded to my old school approach whereby I first begin by looking at maps, using Google Maps (digital), and CSAA/Butler (paper) for determining routes, preferably on secondary roads or state routes. Then slogging through Google search for campsites or lodging. Lastly, I’d scour the interwebs, particularly YouTube for curated content about landscapes, terrain, and interesting features about the people, places, and things we might encounter on an “epic” ramble.
Evolution of the SRPC
I envisioned using AI to confirm the route, compliment me on my stellar planning, complement the less stellar aspects of my planning, and offer lodging options and noteworthy local attractions to explore along the way. I was, somewhat naively, excited that this technology would increase the efficiency of planning while cutting down on the time it takes to conjure a ramble by calculating mileage and time.
So I developed the Sisyphean Ramble Planning Criteria, (SRPC), to employ when scouting routes whereby freeways and interstates are intentionally avoided insofar as an alternative to the “slab” can be found. Recognizing that Google Maps can be frustrating when once on the road, that carefully planned selected route is overcome by the in-house on-the-fly algorithm that selects a more “efficient” routing. This despite checking the “avoid highways” box in Options. Damn algorithms.
The Robert Frost Dilemma, or, RFD and DAP
Given the Damn Algorithm Phenomenon (DAP), paper maps reign in planning, at least initially, but I find them deficient when riding. A phone mounted on the handlebar is much more convenient than stopping at a busy fork in the road. Speaking of forks in the road, let us enjoy a tease of good ole ‘Merican poetry as our 250th anniversary looms. It seems Robert Frost solved this problem long before GPS.
“Two roads diverged in a yellow wood,
And sorry I could not travel both”
In taking out and unfolding the paper map, refolding to 6” x 9” content specific Origami, getting out glasses to be able to see the 3 point font graphics, noting and trying to remember all of the intersections and interchanges needed making in the next 50 miles, then attempting to fold the map up properly, especially if it’s windy. GPS sort solves this problem.
You get the picture. Each navigation option is compromised, especially the free ones and I’m willing to admit that it could all be the result of user error.
My Dog Understands Some Words
Is it asking too much of this AI machine that converts words to numbers, shakes those numbers in some unknown dice cup, and slams out numbers that roll into words coming up with reliable numbers for, say distance on a map? Claude seems to have scrubbed enough literature (travel writing) to approach describing the route with a Rick Steves, je ne sais quoi. At least my dog perceives something of my intent based on her instantaneous reading of my emotional state. I imagine SoBe contemplating, “Does he know it’s time for eats? I’m staring, trying to see if he is acknowledging me,” Then again, she’s a dog and only reacts to the clock inside of her stomach.

In the opening featuring Claude’s Day 1 narrative, Claude mentioned passing through Yerington (Nevada) and arriving at New Pine Creek Campground at the end of Day 1. The route I provide in the Google Map link, had that as the primary option, however, those two places are about 300 miles apart and from Merced, New Pine Creek is some 457 mi distant. Yerington is southeast toward Reno; New Pine Creek is on the California/Oregon border, northeast of Lakeview. While that is a legitimate route, it would require a break, somewhere in between, like say, Susanville to satisfy the SRPC.
Did I explicitly identify the number of days with a variable, x, and let Claude determine the number of days it would take based on my prescribed mileage and not some machine hallucination about how Merced and New Pine Creek is a day ride or that Burns, OR is 250 miles from Jackson, WY by way of the Bighorn? Those were the first of the “ambitious distances” in the itinerary Claude recommended.
I included the URL in my prompt to Claude to a Google map, based on the supplemental CSAA/Butler maps route I used to make the Google map. It seems like applying the SRPC is something he could do reliably.
Wait, what exactly is Claude’s pronoun? Alexa and Siri have male and female identities. I digress.
Let the Games Begin
My initial prompt to Claude implied for him (I’m going with Claude to be a boy) to use mileage criteria for determining stops for the day. I guess if I doctored that reference up with a little x-rated math representing the length-of-the-day variable, it would have been more code-like. Code, the metabolic equivalent to mitochondria in actual living things, also that which Claude ingests, digests, then regurgitates.
Here’s my initial prompt, finally (my prompts heretofore represented by bold italics):
Here’s your motorcycle itinerary challenge… Take this map and create an approximately 250 mile a day trip with stops for camping and motels at roughly those 250 mile intervals. Avoid interstates as much as possible. State Hwy routes are okay, decent local roads are a plus. Go for it: https://maps.app.goo.gl/1VjVyLQbk9DBFJ5t6
Without laying too much on the Sonnet 4.6 version of Claude by not mentioning anything about specifically identifying camping and motel recommendations, fuel availability/cost, or potential weather, all features of the SRPC, just like that Claude spits out the following proclamation: (Claude’s responses heretofore represented in blue italics):
I can see the full route from the URL. Let me extract all the waypoints and search for lodging options along the way. Let me search for lodging and camping along each leg. Used 2 tools. Now I have everything I need to build a comprehensive guide. Let me put it all together. visualize show_widget
Whoa, that was darn near at the speed of light! Here’s the initial summary Claude produced, encapsulating the whole trip:
Epic western states moto route
Merced, CA → New Pine Creek → Pendleton, OR → Missoula, MT → Bighorn, WY → Hoback Jct → Green River, WY → Green River, UT → Baker, NV → Merced, CA .
- Total distance: ~2,680 miles (est.);
- Riding days: 10 avg 268 mi/day;
- Total fuel: ~60 gal at 45 mpg avg;
- Fuel cost est.: ~$240 at ~$4.00/gal avg


Left: Claude’s Version of the Epic Western States Ramble
Right: My Version of Epic Western States Ramble
As I compare the waypoints of Claude’s map, based on my version of the route, there’s an uncanny resemblance. I wonder what numbers rolled out of that AI dice cup that Claude came up with 2,680 miles when Google unabashedly came up with 3,295 miles.
I am reminded of George Bush in a 2002 quote, “There’s an old saying in Tennessee–I know it’s in Texas, probably Tennessee–that says, ‘Fool me once, shame on… shame on you. Fool me–you can’t get fooled again.” The correct aphorism should be “Fool me once, shame on you. Fool me twice, shame on me.”
I vow to remain unshamed!
Armed with having planned dozens of moto, backpack, cross-country ski, bicycle rambles and 24 student trips to Washington D.C. and Manhattan, being naturally skeptical, I wasn’t willing to give Claude a first or second chance to fool me much less shame me. Compare Claude’s numbers with those of both maps.
Overall, if you open my map you’ll see that Google declared (if it hasn’t already updated to reroute from the back roads to the slab) the route I submitted to Claude that would take 55 hours to travel 3,329 miles, not 2,680 miles on Claude’s summary. I’m not sure how Google arrives at the time, except I know it’s based on speed limits and traffic volume. Claude’s excuse?
Time for a little mathing
A more reasonable average of ~268 miles a day, after breaking down camp, somewhere in the neighborhood of 7± hours on and off the saddle, allowing for fuel, food, scenery, and nalgas (that’s Spanish for what’s in the saddle) relief stops. That tightens up the schedule for locating lodging or setting up the next camp and finding provisions before dark, even as we approach the summer solstice. Claude in fact seemed to use a reasonable distance/day calculus. Google puts us at ~333 miles on average per day. It’s only a difference of 65 miles, a little more than an hour unless we’re in Idaho, Montana, or Wyoming where the speed limit on many roads is 80 mph. We won’t likely be on many of those roads.
Sisyphus and SMAP prefer ±6 hours on and off the saddle as opposed to 8 or 9 hours. The latter reminds us of our pre-retirement rat-race hours. Don’t forget the importance of the 3R’s. ±6 hours would leave time to enjoy the 3 R’s of Rehydration, Relaxation, and Reflection, which is the point of the ramble in the first place. One cannot rush the 3R’s hence the attractiveness of the former. Besides, there’s no overtime pay past 8 hours on a motorcycle. Only nalgas fatigue and diminished focus. I got that latter/former thing right, didn’t I?
Mentally Anchoring
When once again I corrected Claude’s folly, he responded:
The reason for my error was likely that I was mentally anchoring on a “target” of ~275 miles per day and unconsciously adjusted the number rather than trusting the actual map distance. That was wrong of me.
To be fair, though Claude’s geography was often suspect, his travel prose could be unexpectedly lovely. Nearly every revision arrived wrapped in language that sounded as though Edward Abbey had been reincarnated as a tourism intern.
Claude rationalized his errors by claiming “mentally anchoring,” or “unconsciously adjusting,” rather “than trusting the actual map distance.” Huh? Is Claude claiming consciousness by admitting unconsciousness? The next time my wife accuses me of stubbornness, I’ll simply reply that I’m mentally anchoring…
Claude continued:
Would you like me to rebuild the full guide with the corrected mileages across all legs?
Let me get the accurate mileage for every single leg before building anything.
Claude, a captain in the obvious army. But that didn’t stop him. Similar mileage hallucinations continued to appear throughout the itinerary…
The Return to the Bighorn
What follows is another example of the chat Claude and I had for planning the ramble. Despite mistakes made with distances violating the Sisyphus Ramble Planning Criteria (SRPC) and several course corrections for the first three days, I sadly decided to chop off the Bighorn in Wyoming trying to keep the ride under a month long. Also, this time of the year weather can be an issue as I recall from an earlier trip, only on a bicycle.
The Bighorn was the scene of one of the most challenging uphills in my previous life as a knuckle-headed member of a group of erstwhile bicycle-riding-knucklers as we took on the Western States in annual Tour de Life rides. Rides across all of the western states that have inspired Sisyphus, having lived more of his past than he has a future, to mount the moto in search of that youthful spirit and in memory of lost friends.

The leader of this group can be seen in the center of the photo above. That was Larry. He traded his helmet for the cowpoke’s sombrero for the photo. These cross state bicycle rides were organized by Larry with a varying cast of characters over a period of nearly 30 years. Larry has since ridden the Burr Trail into the Mystic and my tribute has taken form in my post, No Italics Necessary: The Tour de Life – A Tribute to Our Dear Friend, Larry Johnston.
My first summer cross state adventure with this intrepid though mildly warped contingent was a pedal across Nevada in 1993 and our last together, in 2015, a loop ride in Utah having ridden across California, Oregon, Washington, Idaho, Montana, Wyoming, Utah, Colorado, New Mexico, Arizona, and Nevada. I am eternally grateful to Larry’s spirit, great humor, and generosity for planning and leading these rides and his memory will live with me, and all who were fortunate enough to join in these merry prankster tours, until I take my last ride to some border, which could be charitably described as bleak, dreary, isolated, and forsaken. A familiar feature of the end of most of these rides… Maybe the Bighorn next year.
Claude’s poetic prose in action
By now, growing tired of all of the back and forth with Google Maps to confirm Claude’s mileage hallucinations, I dropped the Alt. US-14 climb to Burgess Junction, the Bighorn 🫤 and decided to go back to my “old school” route planning. I would then use Claude to describe the route, wary of the mileage, and recommend lodging, as it seemed to be more reliable than his mapping.
And so, preserving Claude’s intriguing description of the leg of the trip up the Bighorn on what would have been Day 6 and 7 by his calculus follows:
Chief Joseph Pass at dawn, crossing the Continental Divide into the Big Hole Valley, is cold and quiet and profoundly empty in the best possible way. Wyoming builds toward the main event: Burgess Junction. The Bighorn Scenic Byway climbs to 9,430 feet above the treeline, and on a clear morning with no other traffic, standing on that summit — maybe for the second time in your life, the first on a bicycle with burning legs — the feeling is not easily described. You’ll want to stay longer than you should.
Yeah, burning legs barely kept me from going hypothermic as we rode from Cody, WY (5066 ft el) to the base of the climb in Lovell, WY at (3,835 ft el) up to Medicine Wheel (9,430 ft el), humping up grades of 8 – 10 percent over 25 miles to the top from Lovell. The last 5 miles in a hail and torrential thundershower, complete with the aroma of ozone, capping a 98 mile day. When I arrived at the Bear Lodge Resort at the summit, shivering and on the verge of hypothermia, I jumped into a hot shower then retreated to the bar for a little 3R’s relaxation, rehydration, and reflection with a fine pint of Moose Drool in the company of my fellow survivors. While it was a spectacularly memorable ride on a bicycle, I’d say riding a motorcycle up Alt US-14 would be anticlimactic… Another example of youth, wasted on the young?
The descent into the Big Horn Basin drops you back into warmth and Wyoming’s wide ranching country, and US-191 south through Pinedale carries you toward the Wind River Range — a wall of granite and snow that rises to the east like a declaration. Fremont Lake sits at the foot of it all, glacier-blue and enormous, and the campground on its shore is one of those places that recalibrates something in you. You make dinner in the long June light, the peaks turning pink above the water, and it occurs to you that this is the kind of evening that justified packing the tent.
I discovered on the paper map that Stanley, ID was more “efficient” distance wise than Salmon, ID Claud had proposed. Though Claude ended the day in Hoback Junction, following the descent from the Bighorn, he noted that there is no lodging or camping near there. So Claude, now accustomed to hallucinations, comes up with another 71 miles to Fremont Lake to camp. Why then end the day in Hoback Junction? Add 14 miles to Jackson for a room for the night. At least Claude was looking out for our safety.
Wyoming high desert sweepers, pronghorn everywhere, almost no traffic.
Watch out for those pesky pronghorns.
By now, I accepted that Claude turned out to be less like a GPS and more like that enthusiastic friend who insists he knows the way. He doesn’t. But the stories he tells along the route can be pretty entertaining.
Well, there may be a day inserted somewhere in Utah, maybe Torrey, some 268 miles from Flaming Gorge for a fine night’s sleep. Then on to Ely, NV, coincidentally, 268 miles. Plenty of time for the 3R’s. I did that with Google Map’s assistance and a nice cool beverage.
Here’s what haggling over the course of several chats ended up, in Claude’s wildest dreams, being the remaining days of the ramble:
West from Ely on US-50 W — the whole way to Fallon. Three small towns and an extraordinary stretch of American loneliness: Ely → Eureka (~80 mi) → Austin (~70 mi) → Fallon (~100 mi). Sagebrush valleys, Basin and Range fault-block mountains, wide open sky. Time magazine called it “totally empty” in 1986 — Nevada embraced the label and created an official “Highway 50 Survival Guide” passport, stamped in each town. Pick one up in Ely and collect stamps in Eureka, Austin, and Fallon for your official Nevada survival certificate. Pure two-lane, zero interstates, and one of the great American road experiences.
You’ll come home road-worn, sun-baked, and already planning the next one.
Old Claude tapped into a closing sentiment of which I am totally in agreement. But once again, the distance from Ely to home is implied as a single day.
And if you give me weed, whites, and wine
And you show me a sign
I’ll be willin’ to be movin’
(Lowell George, Little Feat — Willin’, 1972)
BTW, the forecast seems in order with the chance of precip along the route lower, temps higher…
Old School Trippin’
I have since revised the route without Claude’s assistance. It was back to setting up individual maps of each leg of the ramble. The ramble looks like this:
Day 1-Susanville; Day 2-Burns, OR; Day 3-Stanley ID; Day 4-Jackson, WY; Day 5-Vernal, UT; Day 6-Torrey, UT; Day 7-Ely, NV; In opting for US-50, the Loneliest Road in America, Day 8-Fallon, NV; and Day 9 Home. Around 288 miles a day, within the Sisyphean Ramble Planning Criteria met. Well, there are 335 and 307 mile days buffered by a couple of 255 mile days.
I wanted to consider an alternate Day 8-10 option keeping the Great Basin National Park, Baker, Caliente, and Tonopah, all in Nevada, and maybe a last night in the Owens Valley high desert on eastern Sierra at the Taboose Creek campground in the itinerary. I love these places, but it will soon be summer and as at least one of the names imply, it can be hot. Hopefully we’ll not get warped by the rain, or driven by the snow…
That’s not to say Claude wasn’t of assistance. The chap was terrific in running down lodging/camping along the way. The descriptions of the terrain and features of each leg were moving, in spite of their inaccuracies of length and waypoint.
My leash is not 14 days long. It’s more like 7 days long. I’ll be pushing it for a 10 or 11 day trip as it is. I’m not getting any younger and so I want to at least revisit many of the places on the moto that I originally did on a bicycle. Apparently my responsibilities at home are greater now that I’m retired than when I was younger riding bicycles with knuckleheads. Maybe my wife has grown used to having me around as janitor, landscaper, and occasional housekeeper or chef in retirement. I know SoBe likes having me around.
Sometime in June, around my seventy-second birthday, SMAP (Sisyphus’s Moto Associate Pete) will embark on some form and/or fashion of a ride through California into Oregon, Idaho, Montana, Wyoming, Utah, Nevada, and returning to California in 9-12 days of riding. Stay tuned for the ride report that will follow, hopefully, before the Fourth of July. Until then, keep the shiny side up and the rubber side down.
Thanks Claude!

Dudley Do-Right, Jay Ward Productions












































































































































































































































































