Depending on what kind of look you'd prefer, and also what sort of land area you want to map, you might also look at World War 2 Area Maps (which has options for illustrative contour lines), Cthulhu City (which also includes illustrative symbols for a selection of building types, albeit with "Call of Cthulhu" elements about some) or the Tactical Maps pack from last year's Annual.

The lower cliff edges could perhaps do with something to help them "sit down" in the terrain better; they have rather too crisp an edge currently, whereas in reality, there'd be some snow drifted or fallen around the base to make the edge a bit more irregular.

I agree the right side version looks better.

I'd suggest making the "contour lines" round the tops thinner and less distinct - closer to how the hatching is drawn, as they seem too dominant otherwise at present.

Not sure if it might be worth trying with a tool that generates longer hatching lines instead of having to draw two or three sets together for the steeper areas. I've a feeling the law of diminishing returns is liable to set-in with too much experimentation, however.

Glaciers might work with a more transparent version of the fill you have showing the seas right now (not sure how the style generates that appearance, so this might need extra work). The original book map looked to have a scattered series of small pale blue dots and tiny circles to show the glaciated tops.

The book-map lakes used a lot of lines drawn parallel to the lake banks right into the lake's centre, more or less, which was also how the seas were shown, although that looked uncomfortable to my eye, so you might want to try that, or maybe tone it down a bit.

It really depends how close a match you want to that original Northern Italy map you linked to.

Looking closely at the book's image, it seems they used mainly one set of hatching lines to represent the general appearance of the landscape, with denser, longer hatching for what I imagine would be higher peaks and ridges, less dense, shorter hatching for lower hills. Occasionally, there is more than one such set of lines (Mt. Viso, a little below the 45° line on the map's left edge, has some complex examples, for instance), but this seems fairly rare, often used only for some of the higher, or possibly larger, more complexly-formed, mountains.

In places there does seem to be a "contour line" drawn for some - but by no means all - of the unhatched higher areas and hilltops, though that seems to be sometimes only on one side of the top, or only around part of it. In some cases, this seems to be an illusion due to the density of the landscape hatching lines. In others, it looks as if it has been drawn to show ridge or scarp features partway up a hillside too.

Similarly, the line density and direction can be variable in different places around the same peak or along the same ridge, probably to show ridges and spurs, or other smaller features, that can't be shown just using the "hatch and bare hilltop" style because of their sizes.

Unfortunately, because the map looks to have been drawn to try to replicate much of the overall patterns shown by the actual landforms, I'm not sure creating drawing tools will allow a very precise mimicking of the style, and might need to be done almost entirely by-hand, like the original. As I said though, this really depends how close a match you need your version of the style to be.

As Sue suggested, what you have now is a perfectly reasonable facsimile overall, though I would probably make less use of the dashed "contour lines". Maybe think of adding some of those blue speckled areas for the icy, glaciated highest peaks as well?

@Fersus - If you have the solo rules ("Strider Mode") for The One Ring, which are only available as a PDF still, as far as I know, those do add some more journey options which could be adapted for group play, or perhaps would help spark ideas. I've not played TOR yet, but it did strike me when just reading through all the rules (I have everything that Free League have published for it so far) that a lot of the random result tables generally were too short, so would be apt to become repetitive. I like Ralf's use of pre-prepared options along with the random rolls to make things more interesting overall, since as GM, you can't always come up with some worthwhile variant every time the same roll comes up otherwise.