Anxiety typically arises early in childhood and decreases during school age. However, little is known about the earlier developmental course of anxiety in preschool, especially in at risk children, posing a clinically important problem. Given that anxiety in youth has a chronic course for some and also predicts later development of other mental health problems, it is important to identify factors early in development that may predict chronic anxiety symptoms. At-risk children (oversampled for depression) and caregivers completed 6 assessment waves beginning at preschool age (between 3–5.11 years of age) up through 6.5 years later. Growth mixture models revealed 4 distinct trajectories: 2 stable groups (high and moderate) and 2 decreasing groups (high and low). Important to note, the high stable anxiety group had greater baseline depression and social adversity/risk, higher average maternal depression over time, and poorer average social functioning over time compared to the high decreasing group. The high decreasing group also had greater externalizing/attention deficit hyperactivity disorder scores than the low decreasing group. Children with anxiety in early childhood who also experience high depression, social adversity/risk, maternal depression, and poor social functioning may be at risk for chronic symptoms over time.