Regional anesthesia and analgesia are integral to modern perioperative medicine and contribute to multimodal analgesia and enhanced recovery protocols. Over the past two decades, regional anesthesia practice has changed dramatically with the incorporation of real-time ultrasound guidance. Anesthesiologists in the U.S. who completed residency training in the early 2000s were not routinely taught how to use ultrasound for regional anesthesia, and subspecialty fellowships in regional anesthesia at that time were relatively few and varied widely in terms of educational experience. Today, the state of regional anesthesia education in the U.S. is completely different and has embraced a multipronged, multigenerational approach that addresses the needs of anesthesiologists in training, as well as anesthesiologists in practice throughout the career lifecycle. This review will cover the current state of regional anesthesia education for residents, fellows, and practicing anesthesiologists and will note important historical advances, as well as future trends that may shape the curricula for regional anesthesia learners in formal training and continuing education.