Short answer: it’s always a good time to apply for scholarships! Opportunities open (and close) all through the year. The best way to win money is to send out as many applications as possible. The best way to do that is to make applying for scholarships into a habit. Set a weekly or monthly application goal, then do your best to meet it. Certain types of scholarships might be more available at certain times of the year. For example, community foundation scholarships usually have deadlines around February.