Tokyo to Nagano via 299



Maximum Pace
Nov 4, 2006
*Note regarding name clarifications: I stayed in Nagano prefecture, in a small town called “Hotaka” (穂高). This is not the same “Hotaka” (武尊) of the hill-climb race fame, which is in Gunma prefecture.

The first third (or 100km) of the ride couldn’t have been more perfect timing-wise.
I left home just after 21:00, and made my way through to Ikebukuro, and finally onto Rte.254, which would take me out away from the city. I turned onto Rte.463, and did the little zig-zag through Tokorozawa city, and finally onto the Tokorozawa-Iruma By-pass.

56km: At 23:40, I stopped in the small town of Bushi and had a sandwich and filled up my water bottles. I left there just after midnight and continued onwards.

77km: At 0:55, I reached the Rte.61 turn-off. This is the road we usually take when we do the Kaoburi-toge and Karibazaka-toge climb from Deej’s famed “Okumusashi Madness” ride. Of course, I wasn’t planning to take this route tonight, but I stopped to take a photo of the sign, and to have a drink from the vending machine just underneath the sign. I saw a shooting-star, finished my “Real Gold” and had a very "intimate experience with a truck-driver" (Read about it down the bottom of the page).

86km: At 1:25, I reached Shomaru Tunnel. It was my first time passing through it, and from what I’ve heard, it doesn’t have a very good reputation. At nearly 2km, that’s understandable. Personally, I don’t usually mind tunnels that much, but I’ll give this one negative points for being up-hill most of the way. It’s uphill for almost 1.5km, and then flattens out for the last 400m. If you were coming from the Chichibu side, I’d say “go for it!” But from the Tokyo side … Errr, you know!? I couldn’t hold much more than 20km/h, and that translates to almost a full 6 minutes inside the tunnel. However, at that time of night, I was only passed by 3 cars, which is not too bad.

The downhill from there was great, although a little frightening in the dark for the first kilometer or so (I do have a big “Cat-Eye EL520” that puts out a good beam), but you can’t beat sitting behind a truck in these situations, and the 10km trip into Chichibu was over in less than 15 minutes.

99km: At 1:55, I rode to where the “Denny’s” was supposed to be, and then doubled-back, but still no luck. Finally, I asked two locals, who informed me that “Denny’s went bust, but there is a ‘Gusto’ about a kilometer down the road”. I got myself a booth, and settled in for a big meal – Spaghetti & meat sauce, a Gusto-Burger (cheese inside the meat), and strawberry-pancakes for dessert. That, plus the drink-bar easily filled my calorie quota. I wasn’t really sleepy, but I managed a short 15-minutes of shut-eye anyway. I left there at about 3:50, in complete darkness.

A word of warning for those riding out of Chichibu on Rte.299 for the first time:

Just after leaving Chichibu on Rte.299, the road twists and turns a bit, but is quite well marked, so no problems there. However, after a few kilometers, you will pass through the town of “Ogano” (小鹿野). In this town, there are TWO Seven-Elevens. Make sure you get any supplies you might need at one of them – There is nothing after that point for the next 40km!!! Not even a Coke-machine!!! (There are “Dy-Do” vending machines, but if you crave sugar & caffeine, you will be horribly disappointed).

About 5km past Ogano, at around 4:30, the sky began to lighten and the climb up to Shigasaka-toge/tunnel (780m) got gradually steeper. All the while, I was dying for a red & white can of cola… Even a Pepsi would’ve been welcome!

133km: At 5:35, I reached the tunnel and put on my rain-cape for the descent on the other side. After descending for about 7km, I hit a T-junction, and turned left. Less than a kilometer from the turn-off, I was staring at a dinosaur on the side of the road. Dinosaur meant theme-park, and theme-park meant vending machine, and vending machi….. You see where I’m going here!?

140km: At 6:00, I was happily swimming in soda-pop, and posing for pictures. After my bottles were filled, I set out again. The road goes down for a few more kilometers, before it starts its rising once more, not too steeply though, for the next 10km or so until Narahara. There are a lot of touristy, hikey-type shops there, and it’s also the start of the second (and second-biggest) climb – Jikkoku-toge (1,340m).

The gate was open when I went through, but it was clear that it’s closed for most of the year. It’s about 13km to the top from there. The one thing I noticed about this stretch of road was how quiet it was. I had been climbing for about half-an-hour (ie. about halfway up) before I was passed by another vehicle of any kind – in this case, 2 motorcycles with full touring gear. Fifteen minutes later, an SUV and a Toyota Hi-ace. Another 5 minutes after that, a bottle-green Renault (it stopped, and passed me again later), and finally just before I reached the top, one more touring-motorcycle (This guy took the photo of me at the summit – Thanks!) Total: 6 vehicles in roughly one hour.

167km: At 8:00, I finally made it. 2 hours since the dinosaurs, this was a tougher climb than I’d expected. The downhill from there was a little bumpy in places, but I also hit my top speed on this section – 73.5km/h – so I can’t complain. About halfway down, it started raining, so I stopped to put on my rain-cape, booties and cap. By the time I reached Rte.141, where I had to turn left, it was fairly pouring and I was getting hungry again. My first thought was “ramen”. I passed two ramen shops, but both of them were closed. What’s going on? I thought. And then I realized that it was only 9 o’clock in the morning…

189km: At 8:55, at the first convenience-store I came across (it just happened to be a 7-11), and I had the Omelette-rice-doria, and an energy gel. I also bought a piece of fruit-cake (pound-cake?) to have once I got to the top of the next, and longest climb – Mugikusa-toge (2,127m). Thankfully, the rain HAD actually stopped by the time I set out from the 7-11. From the turn-off, it immediately starts going up. No warning! Just a sign that says “9%”. But then when you might expect it to level off a bit, it doesn’t. It just stays at “9%”. Now, I’m trying to do the math – The elevation at the bottom is about 800m, meaning the whole climb will cover 1,300m over 25km – which to my reckoning, means it’s an average of just over 5%. So why is this 9% section so long? Another thing this climb has is elevation markers at every 100 meters of upward travel. About 20 minutes after the turn-off, the first one tells you that you’re still at 1,000m. There are also “curve” number markers, like the ones at the Hotaka-race to tell you how many curves you have gone around since beginning this lunacy. As I was climbing, I remembered Thomas & Sergey’s “Mountain-Madness” thread; maybe I should have read it more carefully, they might have written how many curves there are in one of their posts. In hindsight, I’m glad I didn’t know. It just would have depressed me. But there’s nothing wrong with me spoiling it for you guys though… 64! That’s the magic number – 64 curves to the top.

I also want to quote Lee, in his thread “299 Beyond Chichibu”. In one section, he talks about it being “ambitious”, and then he adds in brackets these few words that would haunt me all the way to the top: “(it's probably way too much for one day)”! The curse of the Wolfman! Thanks a lot, Lee! Just by typing those few words, it made you my constant mental-companion all the way to the top. I hope your ears were burning! I stopped at the 1,800m elevation mark to have a 3-minute leg break (and take a photo), but not long after that the landscape began to change from heavily-wooded to almost flowing meadows of long, dry grass.

It was in this area that the sun also made a brief appearance, and all at the same time I felt, the warmth of the sun, the coolness of the breeze, and rain that wasn’t rain but was the finest of mists. It was one of the most pleasurable sensations I had felt all day, indeed, felt in quite a long time. Maybe it was the slightly lower oxygen level at that altitude, but “Oh my ……. It was SO beautiful. I, I, …DON’T CRY!” One more urge I managed to fight off! From about halfway up, I had started counting how long it took to ascend each 100m elevation jump, and it was usually between 11 and 12 minutes. There is a big discrepancy though, as it only took me 4 minutes to climb from 1,900m to 2,000m – I don’t think those two signs were place very carefully. As I neared the top, the sun disappeared, the breeze turned into a gale, and the “finest of mists” was replaced by rain proper!

215km: At 11:52, I reached the summit riding into a vicious headwind. I snapped some photos, and mailed my wife (Yes! There was reception up there.) A few hundred meters down from the summit on the left-hand side there is a parking area & public toilets. I stopped there to get some shelter from the bitterly cold (but not quite freezing) wind, while I ate my fruit-cake. Apparently, this rain and wind was the tail-end of a typhoon that had passed through Kyushu the day before, and was now NW of my position, heading towards Tohoku. The first part of the downhill was terrible – Barely able to hit 25km/h, at this rate it would take over an hour to get down. Fortunately, with each kilometer, the wind died down and I was able to pick up speed. I was also very much looking forward to some of the warmer air further down the mountain. And this descent is LONG! – Almost 30km of downhill goodness into Chino.

237km: At 12:55, I was basically down from off the mountain, but still a few kilometers from Chino city, itself. I stopped at yet another 7-11. This time, I kept it simple with a mixed sandwich, a piece of chicken, and a multi-mineral gel. But I was now officially behind schedule – My wife’s train would be pulling in to Hotaka station just before 3pm, and I still had over 60km to ride. I didn’t know it at the time, but this would be my last food stop before I got to where I was going. I got rolling again, and made my way past Chino station, and finally onto Rte.20, which I took all the way through Suwa-city and up the short climb to Shiojiri-toge. From there, I had a wonderfully long (and once again, truck-assisted – at 50-65km/h all the way) downhill to where Rte.20, as a road, abruptly ends and is replaced by Rte.19. Technically, Rte.19 is a kind of T-junction, with one way heading SW to Nagoya, and the other heading directly north to the Japan Sea. I was heading north, which meant turning right at the intersection.

271km: At 14:40, where Rte.20 ends, I stopped to check the map. I had to turn right onto Rte.19 towards Matsumoto. This was essentially the final stretch, and thankfully, the same wind that was beating at me on top of Mugikusa-toge was now pushing me forward at a very reasonable rate – between 40-45km/h for a lot of the way, where traffic permitted. At 15:00, I stopped a few kilometers south of Matsumoto to call my wife and tell her that I would be there in about half an hour. I finally arrived at Hotoka station at 15:50, with the meter distance reading exactly 300.43km. I relaxed with a can of “Real Gold” and a shu-cream. All in all, I was 2 hours later than I expected to be (so much for arriving in Matsumoto by 1pm, eh!) and I can attribute that to Mugikusa-toge! It really is a true beast of a climb.

My last overnight adventure, “Tokyo to Nagoya”, which was a total of 438km, was done almost completely on flat ground – albeit, in quite windy conditions. This one was considerably shorter – shorter even than to Niigata, at 358km – with a total of exactly 300km. So which one was tougher? I would have to say that even though it’s shorter, the hillier ride is more draining. And here’s why: When you are riding on flat ground, you don’t have to put out a lot of energy – especially if the drive-train (gears, chain, and wheels) is running smoothly – you can essentially “feather-pedal”. My very first cycling mentor used to put it like this, “The bike does 25km/h by itself; you don’t have to do much more to get it to 30!” Whereas riding uphill forces you to put out a requisite amount of watts just to stay upright. And then even more, if you want to go forward at a decent pace.
Anyway, that’s another adventure over and done with. Except the following day, my wife has made me promise to go on a 130km hill-climb ride with her. But that’s another story.


An Intimate Experience with a Truck Driver

So there I was at 1:00am, on Rte.299 just south of the Rte.61 turn-off, about 9km from the Shomaru tunnel. I had stopped at a vending machine for a "Real Gold" caffeine/vitamin drink. The cans are fairly small, so once there's only a small amount left in the bottom, you really have to throw the can and your head back hard to get those last few drops.
And this time when I did just that, I couldn't have been much luckier; Right at that instant, a shooting star (actually, a meteor) streaked a short straight line in the sky directly above me before disappearing.
Apparently it’s that time of the year for the Perseid meteor shower. Anyway, that was the first one I think I’ve ever seen in Japan.
I set off after that, and the road bends around first to the left, and then very slightly to the right. I was fiddling with my bike-meter to check the current mileage - that way I'd know how far I was from the tunnel at any given time – and as I looked up from the meter, WHAT THE ...!!!?
Probably not more than 15m in front of me, where there should have been nothing, was not just one set of headlights, but two. And not one behind the other, as one would expect, either. Nor were they the headlights of a passenger vehicle, SUV, or even a pick-up truck. No folks! The first (normal?) set of headlights, in the far-right lane - the proper lane for vehicles heading in the opposite direction - belonged to a truck; quite a big truck, in fact. Although I can't say for certain exactly how big it was, as my attention was immediately drawn the other set of headlights in what was technically MY lane - the proper lane for vehicles heading in the same direction as myself. This set of headlights belonged to an even larger truck. One that was moving even faster than the first, on account that it was doing the overtaking! Bottom-line, if I were a motor-vehicle, I would have been toast!
You know when you have those moments of just being "in the zone"? Usually when you’re playing a video-game, or something like that. It was one of those moments, but with a slight difference; this time two peoples’ fates (and wheels, and body-parts) almost became very messily intertwined.
Similar to the instants before any crash or near-miss, thoughts come in crisp and clear, and are over in milliseconds, but they are very precise and defined; almost audible. The first of which, was of course, "Oh no!" all in one syllable. The second and more relevant thought was, "He shouldn't be there!"
I know it may seem obvious, but that was the cognitive process at work; breaking down everything into its simplest, most uncluttered components before making a decision. HE-SHOULD-NOT-BE-THERE!
Options: Move as far left as possible!
Other options: Move-As-Far-Left-As-Possible!
Fortunately, the lanes on that particular section of road, while only being a single lane each way, are actually quite wide due to the amount of truck-traffic that passes through. Also, there is an extra 40cm (15 inches) or so of cement gutter to give a bit more lee-way. And therein was my mission: Move onto the cement without hitting my pedal on the vertical edge of the gutter, shift my center of balance to the outside, and hope I don’t get sucked under one of the eighteen wheels!
Finally, and it was almost intimate, there was a very real connection between rider and driver, and as I mentally chanted, "See me!", "See me!", "See me!" ... He DID!
There was a sense of shock, of course, but more than that was a very clear sense that we were both thinking simultaneously, “DON’T PANIC! I’m a professional. You’re a professional. Let’s just hold it as steady as we both can, and …..”
*Note: No! I’m not actually a professional cyclist, but I was dressed like one, so how was he to know the difference? (And I’d like to think that I am, if not “professional”, at least “pretty good”.) And as I said, I’m pretty sure he was hoping I could control my bike, as well as I hoped he could control his truck.
Anyway, I was riding up the slight incline at about 25km/h, and I'd estimate his downhill, overtaking speed to be between 70-90km/h (there's no way to be exactly sure), but when we were about 5 meters from each other, I saw his line shift ever so slightly towards the center-line, and away from me. I knew then, that I would probably be O.K. As the truck went past, I felt my front wheel getting tugged at by the wind vortexes, and after a tiny swerve to correct, it was all over. As well as not being able to judge his speed, it was also impossible to tell how far (or how close) he actually came to shaving off my right shoulder. Speed alters the perception of proximity (Einstein was right!), so the truck may have been as close as 6 inches, or it could’ve been 3 times that distance away – “A foot and a half! What was I worried about?” Besides, I was 100% focused on my 40cm of gutter.
Here's where the "connection" thing is weird though, at the instant I knew he had seen me, I felt almost certain that his first cognitive thought was exactly the same as mine - ie. "He shouldn't be there!" What’s that all about? I had every right to be there!
Technically, I had right of way on that section of road, but I think his logic was a tad more holistic, as in, "What the hell are you doing on this stretch of road, on a bicycle, in the wee hours of a Thursday morning?" To which I might reply he does have a point.
Of course, that wasn’t my first near-miss with a truck, but it WAS my first “truck-overtaking-another-truck-and-coming-straight-at-me” near-miss. And hopefully my last.
The only question I have left now is, was that a “lucky” shooting-star? And if so, did I use up all that luck 90 seconds later? OR, was it an “unlucky omen” shooting-star that was trying to warn me of impending doom? Maybe it was just a spooky coincidence.



The Crank Engine
Nov 1, 2005
What an extraordinary ride and what a close call! Thanks for sharing your epic tale with us, Travis. :)

PS: Must have been pretty dark out there on R299...


Speeding Up
Jun 13, 2007
Very cool trip, Travis! I am glad your intimate encounter ended without troubles. Would love to see your older (and future) adventures on the blog as well :)


Maximum Pace
Oct 13, 2007
Travis -- damn, man, another great adventure well told! Kudos, my friend. Thanks for sharing.


Jan 13, 2010
Victoria, BC
I did a lot of 299 a few years ago going the other way. Really beautiful. I've wondered about doing it again this summer but not in one day!