Looking for a quaint historical community to explore for a month stay.

Sounds like Lucca would fit the bill. Especially during that time of year. I have known several people that have done extended stays there.

We enjoyed Spello and Spoletto but I think the train stations were a bit out of town

Ever since I visited Orbetello (Tuscany) years ago and walked past a group of students from the Italian school having coffee every day, I have dreamed of one day returning and doing something like you are proposing. I was not sure if you wanted an actual language school, it just came to mind. Anyway, we rented a great apartment in the "new town" and it's a good area for an outdoor lover (biking and hiking trails, etc.). You would have to look into the bus and train options to see if it would work for you.
I know Lucca is extremely popular, but the crowds of day trippers would drive me crazy.
Another place I have not stayed but found drawn to for something like this is Pesaro (Marche).

You might want to narrow it down a bit--north or south, if not region.

Hello tdrussburton, and welcome to the forum. That is quite a kick-off first post.

I spent a month in Lucca last year September into October and it meets some of your criteria. The historic center is inside the walls and is well defined and preserved feeling that way. But that also means it's not much of a sunrise/set vista town but feels more perpetual inside of the walls is that makes any sense. It certainly has many local shops, bakeries and places where only Italian is spoken and the aqueduct built by Napoleon's sister stills brings water to the town faucets and the old people (and us) went every couple of days to fill up their bottles for drinking and coffee. But the streets swell with tourists during the day and you hear a fair amount of English and German in the street. This also means the town has higher tourist priced rentals but also a concentration of a surprising number of good restaurants. These things probably fade in November but as I'm sure you know the other problem with tourist driven places is "the season" and how many things shutter when the season is over.

If you want the all Italian town in this area there is Pistoia which is larger than Lucca but on the same train line to Florence as Lucca and Prato (another town) which is not touristed.

The size of the town you are thinking of makes a big difference - it sounds like you want a very small town connected to a larger town by train. If you want really small you might look into Bagni di Lucca which is collection of small towns outlying Lucca and some are connected by train.

Given the weather closer to the Alps you might think further south headed into November weather.

Siena is beautiful with one of the all time great piazzas but way too touristy if you're looking to escape that.
Arezzo has much less tourist interest and great piazza and is blend of modern Italy on the flat near the train station that gets ancient as you head up the (steep at the end) hill. It is well connected to Florence, Cortona, Perugia, and Lago Trasimeno by train and Siena by bus. If you are there deeper into November these Tuscan towns (especially Arezzo) really lean into the Xmas festas and decorations.
Orvieto is very small but relative close to both Rome and Florence by train.

Two cities I really want to visit but haven't that might also work for you:
Ferrara - historical, 30 minutes to Bologna by train
Ascoli Piceno - more remote than other places 40 minutes to the Adriatic coast

My completely off-piste suggestion would be Venice which you can't beat for beauty and uniqueness. I know it is now largely a tourist attraction but speaking to our host last time he talked about how slow it is in November. Maybe a small place out of the way could give you the kind of experience you're looking for. November weather is a concern there and is also the greatest chance for high water if that is a plus or a minus.

The problem with "anywhere" is that there are too many choices.

Hope that helps some,
=Tod

I would look at / research Mantova. Checks most of your boxes and I always got a nice, local feel when there when I lived a few hours away. Close to lots of great spots and Ravenna / Adriatic coast nearby. Food is so good in this region and I believe it was Mantova where I enjoyed their tortelli di zucca. Would be cool and possibly foggy at that time of year.

Recently I was researching towns with Italian language schools and came across Ascoli Piceno. I have not been there so I do not speak from personal experience there but this small town looks so pleasant and attractive and fits your description perfectly. It is not in a highly touristed area, it has a train station, not far from the Adriatic coast, etc. Looks like a good destination to immerse oneself in a low key way.

If you are looking at an October time frame and want to be close to the sea and warmer weather, maybe head south to Vieste or Trani. In Puglia I thought that Lecce and Martina Franca were very pretty and would fit your descriptions.

Someone already mentioned Spello. That general area is very appealing. Consider Spello, Gubbio, Perugia, Arezzo.

Great idea and the possibilities are numerous.

We were in Lucca on Saturday, November 9th last year, just for the day since we had stayed there on on previous trip. My husband and I love Lucca, but it was pretty darn full of tourists that day. Lucca also has various popular festivals with costumed visitors --- see this resident's blog: https://www.twopartsitaly.com/

Hard to name towns that fit all of your criteria, especially having a train station, but look into Pontremoli, Ferrara, and Lecce. Where we go in Italy is heavily influenced by art and museums, and we often have a car.

@nancys8 is right - Lucca is out for your timeframe. ComicCon comes to Lucca and 80K+ people come into the tiny city for several days. It runs from late Oct to early Nov every year and beside crowds housing demand and pricing spike for that weekend.

=Tod

Siena is my favourite city in Italy - but it's too touristy for what OP wants. Lucca is great, but has similar issues. All things being equal, I've thought I'd happily live in either - then I found a third place that had the same feeling, but fewer tourists. Ferrara has the same medieval feel, A walled city with a great deal of history. It is on the main train line between Bologna and Venice, so has great potential as a hub from which to visit other places,

For that time of year, I would be looking south at Lecce or possibly Monopoli in the Puglia region. There’s a lot of quaint day trips from those two.

Farther north, Perugia or Arezzo - there’s some advantages to being in a college town but still plenty of what you’re requesting.

Mantova can sit in a blanket of fog. I like Mantova - just check the weather for that time of year.

Vieste is beautiful but would not be good in October. Plus, it's remote for many day trips, especially without a car and even then...

I would look elsewhere in the south. What about Bari? Or even Matera? I think a month in Matera would be a dream and there is public transport to other towns. Lecce is a great idea...

Ascoli Piceno is a beautifiué small city, certainly worth considering. We had some rain last time in October but it was mostly lovely.
Sulmona would also be excellent, as well as L'Aquila.
I love Senigallia (Le Marche) --long wide beach for strolling, historic castle in town, few English speakers in October......

I think he most important thing is to avoid places that draw large groups of foreign tourists. It will likely be too much of a temptation to avoid speaking English, both with other visitors and with staff at restaurants and bars who likely speak English if t hey work in hospitality in touristed towns or cities....

We usually go to Italy between September and early January, sometimes in early spring. Most often in November.

One thing I've noticed but don't know how good of a generalization it is, is that the smaller and less touristed a town is, the more trouble you have finding a bar or restaurant with outdoor seating. Even when it is very warm (but note where we live!), it seems like about the end of September in central and northern Italy establishments choose to move indoors, perhaps rather than the server needing to go outside numerous times for just a few customers. So if a big part of your wishlist is to sit out on a piazza or a street, you may well want to look farther south. Or for a town with some tourists to fill the tables, just not crowds of tourists.

Also, the first two weeks of November, you might find more places closed than you expect --- it's a good time for Italians running businesses to take some time off before Christmas season starts up.

Bevagna? Scilla? Monopoli? Siracusa?
Russ, your options are endless.
I am done. The month

I vote for Perugia! It's wonderful.

I'm biased of course, but Abruzzo is wonderful in November. Sulmona or L'Aquila, previously mentioned, are good choices with train stations. Ascoli Piceno is just across the river in Le Marche but also a great choice. November has been mostly sunny in my 5-year experience and comfortable temps, 10-15 Celsius. There is a high-speed train line along the coast, but coastal towns will be quiet by then. Vasto or Lanciano are other good choices for mid-sized towns near but not on the coast. Beyond that, though, you need a car to see the interior of Abruzzo.

As others have said, there are few bad choices! Have a wonderful time planning and we'd love to hear what you decide.

In October, any of the suggestions in the north might still be fine. In November, I'd head south - Trani in Puglia maybe?
Ideal for using the train to go up and down the east coast. Great vibes, excellents local food both restaurantas and fruit and veg shops and butchers to cook your own and fishermen selling their catch down by the port......
https://slowtravelitalyspain.blogspot.com/2023/04/why-i-love-trani.html

@ Russ

Where Nelly lives just west of Sulmona is beautiful. Been privileged to be invited to visit her town. I reckon she knows what she is talking about.

I have a few places up my sleeve that tour sellers do not know about, or their economies of scale models preclude.

Here is one in Elice, Abruzzo on you tube from my mate Vincenzo, an Abruzzi from Pescara who now lives in Sydney Australia.
https://www.bing.com/videos/riverview/relatedvideo?q=vincenzo+plate+elice+abruzzo+youtube+video&mid=C0131541CA64A2CD8748C0131541CA64A2CD8748&FORM=VIRE

His main website https://www.vincenzosplate.com/

It is mainly for Australians, but you are free to check it out.

Russ if you think Elice, Abruzzo is the type of getaway you have in mind, I may have some more for you.

If you are determined to restrict your choices by eliminating the car choice, you may well find your self limited to the tourist magnets.

Regards Ron

Russ,
Draw a line from Parma to Ravenna. The train runs straight through Parma, Modena, Bologna to Ravenna. We stayed in Bologna, which is a hub, and day tripped to Parma, Modena, and Ravenna. Ferrara is north, as is Venice. The mosaics in Ravenna are stunning. Florence was a couple of hours west. All our travel was by rail. Lots of piazzas to explore.