Emphasis on 21st Century Skills development has increased expectations on teachers to take advantages of emerging technologies to support student learning. Yet it is not clear whether teachers are well equipped with the necessary skills, support, and positive attitudes toward integrating them in their practices. Even though student-centered teachers are considered receptive to collaborative technologies and likely to use technology meaningfully in teaching, to what extent teaching style influences their Web 2.0 adaption requires further investigation. This study attempts to identify K12 teachers' attitudes toward the use of Web 2.0 technologies in their teaching. 161 teachers from eight middle and high schools in both rural and urban locations of West Virginia participated in this cross sectional survey study. Overall, the findings indicate that while teachers are fairly proficient in their computer and internet skills and have fairly high computer self-efficacy, their workload and a structured and standardized curriculum were inhibitors of Web 2.0 adoption. Age, self-efficacy, workload, and views about Web 2.0 in teaching were observed to be significant factors predicting teachers' likelihood to find Web 2.0 appealing for teaching. Teaching style was not a significant predictor. The findings suggest infrastructural improvements, workload adjustments, and increased professional development opportunities allowing teachers to observe, discuss, and practice Web 2.0 technologies in their particular disciplines.