Preschool teachers have the opportunity to facilitate children's play with a variety of classroom activities. Preschool activities can be categorized as masculine, feminine, and gender-neutral based on children's preferences. Understanding how and why teachers facilitate children's play with feminine, masculine, and gender-neutral activities is important because children's engagement in gender typed activities has been linked to cognitive development. The current study extends previous and outdated research on teachers' engagement in gender-typed classroom activities by using a teacher-focal observational coding system and survey data to assess the frequency at which, with whom, and why teachers facilitate feminine, masculine, and gender-neutral activities. Results reveal teachers facilitate gender-neutral and masculine activities more frequently than feminine activities. However, facilitation of these activities is qualified by with whom the teacher interacts and the classroom context. During free play, teachers facilitate gender-typed activities in stereotypic ways, facilitating masculine activities with boys more than with girls and feminine activities with girls more than with boys. Although, during structured settings, teachers do not facilitate masculine and feminine activities at different frequencies. Finally, in both free play and structured settings, teachers' gender attitudes do not seem to be strong predictors of their facilitation of gender-typed and gender-neutral activities with the exception of teachers' facilitation of feminine activities during structured settings. The present findings address important issues in educational and developmental research by investigating teachers' gendered classroom practices.