You can join a drug plan starting on October 15 and continuing through December 7 [of each year]. In most cases, if you don't join during this period, your next chance to join will be October 15 [of the following year] and you will have to pay a penalty for the months that you were without some form of creditable prescription drug coverage. And this means you pay a higher monthly premium for as long as you have Medicare prescription drug coverage.
(Source: U.S. Department of Health & Human Services)