Directly from Apple? Never. Third-party sellers like Target, Walmart, and Best Buy (IIRC) will frequently discount the remaining colors of a "season", around the end of that season, but that's hit-or-miss. Beyond that, /r/AppleBandMarket or eBay will frequently turn up "new in box" (occasionally unopened) bands. (On eBay you have to be wary of sellers who use Apple's original photos to advertise, then actually ship cheap silicone knockoff bands.)Do Apple official watch bands ever go on sale? I saw nothing on black friday or Cyber Monday.
If you see a band that you really want, buy it. Do not wait for it to go on sale unless you want the possible heartbreak of never getting it at retail prices. There is a long list of folks, including me, who wish they had the Ultra Violet band. I have a few others I wish I'd have purchased but wasn't fast enough. Hyper Grape and Dragonfruit are two recent and popular examples which sold out faster than some of the others. End of season sales do happen. Some of them can be quite good but you're rolling the dice with which ones will be left and on sale.just looking basically a yes/no or possibly the best time/place to look. Not looking to go through 186 pages of reading material...but thanks anyway