Form full context, see here: https://www.docdroid.net/5vuuiCe/img-20170821-0002-new.pdf
Note: While writing this question I noticed that there is a second way to interprete カラオケに合わせて. The reason I didn't settle for this second version, which seems much more correct from a grammatical perspective, is that it sounds odd to me "to match Karaoke". I must add now that I'm not very familiar with Karaoke and that I regard Karaoke not as "music" (which you could "match") but as a form of leisure activity in which music plays a major role.
The sentence in question: 世界中の町で、子供からお年寄りまで、家族や仲間と、カラオケに合わせて楽しそうに歌っている。
First, my first attempt at translation: "In cities around the world, from children to senior folks, with the family and friends, one sings happily... ...joined in Karaoke (?)
according to http://jisho.org/search/awaseru is a transitive verb. It's semantical spectrum seems to be situated around the concept of "coming together", "being together" etc.. Basically, I interpreted カラオケに合わせて in an adverbial function to the predicative 楽しそうに歌っている. My problem with this is that 合わせる is transitive, and I can't help but think that I used 合わせる in an intransitive manner here :/ If it was in passive, 合わせられて, I wouldn't mind it, but since it is still in its active form I fear that did something wrong...^^
Second, my second attempt at translation: "In cities around the world, from children to senior folks, with the family and friends, one sings happily... matching Karaoke."
As mentioned previously in my note at the beginning of this post, this seems to solve the problem of my first attempt by simply using 合わせる in a transitive manner. However, I'm not sure wether this translation is legit since it requires a certain concept of the term "Karaoke" of which I can't say wether it is common or not.