Background
This quote was given to me by my dad in a conversation about Irish folklore. He’s from Northern Ireland, hence the connection. He doesn’t seem to have a particularly strong connection to it though. It seemed to be something he remembered offhand. I’m not sure if he even remember when he first heard it, except that it was just an old Irish blessing.

Context
This is often seen to be one of Ireland’s most famous blessings, but the context is hard to pin down. It was originally part of a larger piece, involving additional lines on the sun and rain, in addition to the wind. In full, his was largely interpreted to be a reference to the holy trinity, as described here:
https://www.irishcentral.com/culture/road-rise-meet-you-irish-blessing-meaning
However, others point out the frequent mistranslations when moving the phrase from its original Gaelic language into English. They also point out how the Celts would often use nature to form godly connections, which illustrates the often difficult relationship irish folklore has when it comes to navigating its celtic origins with christianity:

May the road rise up to meet you: the meaning behind the traditional Irish blessing

Thoughts
I’d definitely heard this saying before. I think the idea of the road rising to meet you is very interesting. Not only is Ireland full of grassy hills (i.e., the rising of the road) but this sentimentality also reflects the strong emphasis on luck the society has. It’s not you going out to walk on the road; it’s the road rising up so that you may walk on it. In this sense, you have no control over the path you take, or over the wind guiding you forward. It’s all a matter of chance, and this prayer simply seems to ask that chance be on your side.