Hi Melanie,
Thanks so much for visiting the Disney Parks Moms Panel. I'm so excited to hear that you're planning your very first trip to Walt Disney World for your group!
One of my family's favorite times to visit is in the fall, and lucky for us this usually coincides with dates when there is a special offer available. The free dining promotion has been available in recent years, but there's never a guarantee this will be offered again in the future. That being said, we can look at information from past years for a clue about when you can expect to see fall deals announced. Historically speaking, the fall free dining offers have been released around May. My best recommendation is to check the Special Offers page of the Walt Disney World website regularly for updates. Even if free dining is not available, another great offer might be available for your trip dates.
Another great resource on this subject is the www.mousesavers.com website. Just search for "historical discounts" and you'll be able to find a page listing past release dates for free dining and other special offers.
I hope this helps with your vacation planning, and please let us know if you have any other questions along the way.
Beth