Walking Up My Sweetheart’s Road

It was interesting to see both versions! They're both great; and while this one is more accurate, your sister's does have a lovely flow to it. I quite like her title as well. Although "up somebody's alley" is an expression that also means "this is exactly their style/the sort of thing they like", so the double meaning is nice.

Până would more commonly be used as "on the way to", but "up to" fits nicely with the imagery of the previous paragraphs.

I had no idea that "up to someone's alley" was an expression. I inserted the "on the way to" suggestion, but how do you suggest that I change the title and the lines that I translated as "up / down my sweetheart's"?
Up / down my sweetheart's street? Uphill / Downhill to my sweetheart's? I think he means to say that his sweetheart's place (street/house) is somewhere in the middle and he goes to visit her from wherever / any point in their village he is.
You know, it's OK if someone likes my translations, but my real pleasure is to know that people enjoy the songs I translate.

We generally use "to" and "from" to indicate going somewhere (like a house) and coming back, but for streets we do use "up"/"down" (though it doesn't actually relate to uphill/downhill in most cases). For example, you'd say "I was walking down the street, when...", or if you're going somewhere in particular, "I was walking up the street to..." And even then, they're quite interchangeable.

Alley(way) is also more commonly used to designate the narrow space behind or between buildings, so I might go with "road". If you want to keep the up/down symbolism, my best suggestion would be "walking up my sweetheart's road"/"walking up the road to my sweetheart", and "walking down my sweetheart's road"/"walking down the road to my sweetheart".

This really turned out nice, you two!!

Yeah, you read my mind, little beast , I want to keep that up/down meaning. Thanks for the suggestions.
Thank you too, brightie, for the encouragement.