(EDIT: Now realize that we could do Matsumoto with either T or T! So perhaps that is not an issue.) I have combed the forum but still can't decide between Tsumago and Takayama. We're taking our first trip to Japan next fall, 12 days in late October/early November, and we'll mostly be sticking to Tokyo and Kyoto, but I really want me some rustic Alps, so we've allotted two nights to one of the Ts or thereabouts. If Tsumago/Nakasendo, we'd go via Matsumoto, which I'd really love to see. But we already have a great ryokan booked in Takayama (Wanosato), and I haven't identified any ryokans quite as appealing in Matsumoto or Tsumago. I guess my main questions are: is Takayama just too touristy? We'd be there on Mon//Tues. And would we really regret not seeing Matsumoto-jo? It doesn't seem like there's anything quite like it even in Tokyo/Kyoto. As much as I'd love to return to Japan after this, it's not as if we'll be going regularly...so waiting until the next trip may not ring true. Thanks in advance for your guidance!

If you are mostly sticking to Tokyo and Kyoto, then yes include Matsumoto for a visit to an authentic Japanese castle; it’s one of the original ones too. Tsumago is an Edo era post town while Takayama is a small city with a big country town feeling. While Matsumoto and Takayama are near the Japanese Alps, neither are in the mountains. To be in the mountains, go to Kamikochi. You can visit for a few hours traveling between Matsumoto and Takayama.

Jonnofor,
I agree with tripplanner’s descriptions of the towns. My husband and I recently returned from our first trip to Japan and we visited both Matsumoto and Takayama. We didn’t go to Magome/Nakasendo Trail, though we did a lovely day trip to Narai from Matsumoto. We loved both Masumoto and Takayama even though they are very different. Matsumoto has a small but stunning original castle. Takayama is very charming - touristy, but not overly so, and has, as tripplanner says, a very small-town feeling., Neither are in the Alps though a day trip into the Alps from either city can be made. From Matsumoto, you can easily visit Kamikochi; while you can also visit Kamikochi from Takayama, I believe it requires 2 buses, but you can easily get to the Shinhotaka ropeway from Takayama.

I took a look at the ryokan that you booked; it’s a bit out of town from Takayama, so unless they shuttle you into town, you’ll most likely be staying around the ryokan during your time there. It looks lovely, but the recent review(s) sound mixed with a decrease in staff since the pandemic and not quite as well-run as it once was.

I’m still working on my trip report, but if you click on my name, you can see photos of Matsumoto and its castle, as well as a lovely ryokan, Yarimikan, where we stayed in the Alps, and the very charming Sumiyoshi, the ryokan in Takayama where we stayed. The latter is much simpler - not a luxury place, but well-run with lovely owners - and the food was excellent.

>> would we really regret not seeing Matsumoto-jo?

That regret is really up to you, but it would be unneccesary. M-jo is one of dozens of other spots in Japan that you could regret not seeing. I want to say that you should not regret it - you will enjoy seeing what you choose and really not have any idea of how much more/less you would enjoy the choice you did not make.

It is possible for you to travel from Tokyo to Matsumoto, spend a few hours to see the castle and then go on to Takayama by bus or train.

The bus goes through the mountains and takes about 2.5 hours. It would be possible to stop at Kamikochi if you had the time (you can't be late for the check-in time window at Wanosato which is 3PM to 5PM).

The train goes more or less around the mountains and takes about 3.5 hours. Best route from Matsumoto is north to Nagano and then shinkansen west to Toyama and then train south to Takayama. The last leg is supposed to be particularly scenic. From Tokyo you could take the shinkansen to Toyama and then go south. I like that route, given that you would be heading from Takayama to Kyoto, because there would be no backtracking like there would be if you went to Takayama via Nagoya.

IDK about ryokan in Tsumago. Are you interested in walking the Nakasendo? You can probably find a nice ryokan somewhere in the Kiso Valley, or maybe over in Gero Onsen. You could try japaneseguesthouses dot com fo see if they have one to recommend. Of course, the go to place to check is japan-guide.com.

Wanosato looks really nice. It definitely has local flavor - look at the photos and it would be pretty easy to guess that it is in the Hida region.

Wanosato is about 20-24 minutes drive from Takayama Station. Besides the check-in time, you would need to meet the shuttle times:
Departure from Takayama Station 14:20/15:20/16:20
Departure from Wanosato 09:00/10:00/11:00

So, Wanosato is a bit remote, and you would need to take that shuttle or rent a car. Taxi might be expensive, if possible. Hida-Ichinomiya Station is 7 min south by train from Takayama and then 7 min by road from there to Wanosato (maybe bus or taxi or maybe they can pick you up there at different times, but it looks like your options might only be the shuttle or car rental from Takayama Station).

Two nights at Wanosato might be one too many if you don't have a car and want to visit Takayama-shi.

If you really want to see a castle in Japan then you can visit Hikone-jo on the way from Takayama to Kyoto or as a day trip from Kyoto (which is what I did). It is a few flat blocks from the JR station and then a short walk uphill on a cobblestone-like road. There is a tourist bus, too, that I took to get to the castle, with a couple of stops (but still the hike up to get to the castle).

Of course, the magnificent Himeji-jo is an easy day trip from Kyoto. The grounds are worth visiting. I visited the castle, inside, many years ago. I visited again a few years ago to enjoy cherry blossoms (too late) and to see a presentation of many bonsai trees. Might be nice for fall colors, but that would probably be last half of November.