Technology integration and Information and Communication Technology (ICT)-based education have enhanced the teaching and learning process by introducing a range of web-based instructional resources for classroom practitioners to deepen and extend instruction. One of the most durable of these resources has been the WebQuest. Introduced around the mid-1990s, it involves an inquiry-centered activity in which some or all of the information learners interact with comes from digital artifacts located on the Internet. WebQuests still retain much of their popularity and educational relevance and have shown remarkable staying power. Because of this, recontextualizing the WebQuest and situating it within the modern-day trend of the "gamification" of instructional design is examined, together with how the WebQuest can promote solid academic gain by placing students inside a learning space patterned after a multi-user virtual environment. This structure includes emphasis on teamwork and socially responsible problem-solving, intense task immersion, task game flow and scalability, and reward cycles. The authors also discuss how including an upgraded WebQuest informed by Common Core Grade-Specific Learning Standards in pre-service education curriculum can advance multiple facets of teacher education with candidates who are acquiring, learning, applying, and integrating pedagogical, technological, and content-area skills. Further, the authors offer suggestions for new directions in the use of web-based resources in 21st century education enterprise.