This research examined K12 teachers’ attitudes toward and experiences with adopting Internet and emerging Web 2.0 technologies in their teaching. Teachers from both rural and urban schools in two counties of West Virginia participated in this cross sectional survey study. The analysis revealed factors such as age, self-efficacy, workload, and views about Web 2.0 in teaching that significantly predicted how likely teachers found these emerging tools appealing for their teaching. Although being a student-centered teacher was helpful, reasonable workload, computer availability, students’ ability to access internet, and clear ideas about how to teach with such tools in content areas seemed to be more essential factors for teachers to develop positive attitudes toward Web 2.0 adoption in teaching. To help this process, this study suggests the need for not only increasing the number of available computers in classrooms and the level of student internet access but also involving teachers in discussion and development of schools’ ICT policies. Further, the study emphasizes the importance of adjusting teacher workload and providing teachers with opportunities to observe existing Web 2.0 enhanced practices in their particular discipline.