Oregon Trail Generation means: A transitional microgeneration born from the mid- to late 1970s to the early to mid-1980s, characterized by its pre-Internet childhood and online adolescence and early adulthood.. It is internet-era slang, commonly seen on TikTok, Discord, Reddit or X. There is no real cause for parental concern; it is descriptive vocabulary rather than risky behaviour. If your teen uses it, context will usually make the intent clear. A short, curious question about where they heard it is usually all that is needed to know whether to follow up.