Hi Mollie! Thanks for coming to the Moms Panel with your question. Unfortunately, we never really know if or when Free Dining dates will be released. Recently, there has been Free Dining offered starting around the last part of August. However, there is no guarantee that this pattern will continue. Your best bet will be to check Special Offers on the Disney World website about once a week to see if or when Free Dining might be announced.
http://disneyworld.disney.go.com/special-offers/ In order to be eligible for Free Dining, you do have to book a package which would include theme park tickets and Walt Disney World Resort accommodations.
Although Free Dining can be a great deal, sometimes securing a discounted "room only" reservation provides more savings once you do the math. Either way, keep an eye on the website and you can determine the best savings for your travel party. Another thing to keep in mind is that almost all full-service dining locations will be completely booked up during Free Dining. This may make it extra difficult to get the reservations that are really important to you. With planning and securing your reservations promptly, this may not be an issue.
One of the great things about planning a trip to the Walt Disney World Resort is the variety of vacation options that are available.
Feel free to come back and ask us additional questions.
Until then, I wish you a MAGICAL vacation!
-Jacqui