Back to School - Registration for Caldwell School District New Student Online Registration is currently open! Skip the lines for Returning Student Registration on July 1, 2019 and register online! New Students: If you would like to register your new student please go to http://skyward.caldwellschools.org and click on the New Student Enrollment. There will be 2 options, simply choose the one that matches your situation and continue with your enrollment. Returning Students: Returning student online registration is open! Parents can log into their Skyward accounts and click on the link named Returning Student. Verify your information and register your returning student. If you have forgotten your password please use the "Forgot Password" link on the log in page. This will send an email with information on how to access your account.