Bottom line again: If your award is unique enough and YOU feel it adds value then add it.
You haven’t said what it is, and no one has seen the rest of your application to judge its worth for your case, you haven’t mentioned any school names so no one knows if they have rolling admissions after a priority deadline, basically no one really knows your specific details nor knows what the AO would do or say in the schools you applied to. Some here will tell you athletic achievements have more weight and should be sent and others may feel social/community recognition hold significant worth. You mention “Regional” award but again that means nothing because a region can be a region of a metropolitan area, a state, a country large or small, or a continent. It’s vague so no one can value it but yourself at this point. It’s opinion here, that’s all.
These are not schools with University of Michigan number of applicants (84,000 applicants in 2022!), not even close. But you shouldn’t be sending updates every time you wipe your nose either! If the argument is made that these schools are willing to take application items such as grades, recommendations, and test scores this late or still putting items in files that students sent in, then schools are still taking application materials. Will it make it into your file, will they be polite but put it to the side, no one here works in admissions, it’s all a guess from everyone here. Your AO can tell you, they ARE still fielding questions, some are still holding events, don’t let people freak you out that they will put a black mark on your application should you ask or send in an update.
So you have to decide if it is worth sending whatever it is in. Would I send a weekly update? Absolutely not. But if it is something like you have shown through your grade report that you get excellent grades and you’ve just been inducted into the National Junior Honors Society, that is not at all a unique achievement, though an achievement, as they already know academically you’re top notch. That wouldn’t add anything more to your cause really. Did you win the greater Milwaukee region Robotics tournament like several hundred or thousand other kids across this country did in their region? Or did you win an award from a region of several countries in Africa where you and your school mates built a windmill that can be used to deliver water to desolate farm lands? Do you come from a school with 50 students who don’t have the same sort of awards and recognitions that schools of much larger student bodies seem to have every other day? Winning a tri-city region writing contest could certainly be a significant award in that situation. See, there maybe differences that are unique for you that no one here can speak to their worth! But even if it IS significant and you send an update, they may graciously accept the information and add it to your file or do nothing with it. No one here knows.
Do what YOU think is best. You may not even do the same thing for every school you applied to. You will not be the only person submitting things even at this late stage of the game should you decide to do that. You will not be the only one to reach out to them and ask should you decide to do that. One update is not going to make them throw your app into the fire.