Although activity involvement has been associated with youths’ social adjustment, shy youth may be hesitant to get involved due to fear of negative evaluation, especially in the context of parents’ psychologically controlling behaviors. The present study assessed youths’ shyness and parents’ psychological control as predictors of youth activity involvement in a grade five Canadian sample (N = 153). Females and youth reporting high parental control reported less sports involvement. Shyness especially attenuated boys’ sports involvement. Being male and parental control predicted less music involvement. Shy youth reporting high parental control were less involved in music and fewer types of activities. Results suggest the importance of parental autonomy-granting to encourage greater activity participation.