YES. But first . . . let me ask you to consider why. What will you be doing with these printed documents that deems them worthy of the ink, the paper, and the time it will take to print them? If your answer is legit, then please proceed!
In this case, this first-grade teacher was wanting to send home some student writing for Mothers' Day gifts. As a mama myself, I know that as cute as it would be to see a digital sample of my little darling's writing, I would want to be able to frame it or put it up on my fridge or hug it or something. By all means, a printer-worthy activity! But what if you left that printing option up to the parents? Maybe some of them would prefer a digital copy so they could email it to grandparents, post it to social media, or even send it to Costco to have it made into a poster! Just a thought: remove the cost burden from your school and make an effort to STOP PRINTING. If parents want to print, then by all means, let them. Using tools like SeeSaw (or hopefully one of these days Google Classroom will add a parent-access feature!) can not only provide parents with that option, but students can also add their sweet little voices, adorable little annotations, and more.
Ok, ok, now that I've ranted about all of that, I will answer the question. The best tool I have found to do such a task is PDF Mergy. Since it's a web-based app, this free service will allow you to merge a bunch of files into a single PDF file. What you do with them from there is up to you.
Choose wisely. ?