TL;DR: you can skate in winter as well as in autumn. As long as it doesn't snow, it's more pleasant in winter.
Contrary to what one might think, it is not the rain that is the main culprit for the slippery road surface. It is the falling leaves. When the rain mingles with the fallen leaves, a film is left behind that is rather slippery. You don't notice anything of it with the bicycle, but you do notice it when you skate, because an inline skater pushes itself sideways at every stroke to get a forward movement, as it were. While pushing, the wheels can slip away on the leaf film. With rain wheels you have much more grip and this effect disappears for the most part (but not 100%).
Autumn is undoubtedly the least pleasant season for rollerblading. An erroneous reasoning, sometimes made by beginners, is: "Autumn is less fun skating than summer. So in winter it will be completely ruined. I'll wait until spring to put my skates back on." There is a mistake in this reasoning.
In autumn it rains more often and when it doesn't, the air is naturally damper so the sun often doesn't have time to get the road surface dry. In the winter, the air is much drier. And most of all: all the leaves have fallen from the trees a long time ago and have been cleared away. No slippery leaves (or leave film) and dry air; that means that you can skate long trips without any problems. There is one exception: on snowy days it is unfortunately impossible to skate with regular skates. With offroad skates you can also skate in the snow, although it is of course different than on clean asphalt.
In this discussion, unfortunately, we have no choice but to mention climate change. Anyone old enough to remember the autumn weather of roughly fifteen years ago will already have noticed that, over the last decade, autumn has become softer and drier (in the north of Western Europe), even to such an extent that it is impossible to call it a statistical fluctuation. It is a tendancy in the Great Story of History, which can already be seen in a small part of a human life: a decade ago I used to find autumn more annoying to skate in than I do now. (To be sure, let us make it clear that we, too, see climate change as a global, threat to civilisation. It is a global problem to which the positive effect on skating is irrelevant.)
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