I know there has been a history of the dining plan offered free in the fall, but is it ever offered free in February? Just curious :)

Hasn't been so far.

Not that i know of, but their is alot of reasons why its mostly fall,
1. Schools are back
2. UK guest come over as thier schools are off
3. alot of people decide if they are going to go around that time of year why not wait for halloween time late october

im sure their are more reasons why

The combination of schools starting and the bad weather has always made late August and all of September a slower time at WDW. Since they have tens of thousands of on site rooms to fill, stands to reason that this is when they offer the best deals.

I've been in the travel biz nearly 20 years, have only seen the free dining program during that time of year, and incidentally, for fairly early booking (an April to June booking period if I remember correctly, for stays during the free dining promo). It's a smart way for Disney to fill their own rooms when the off site Orlando hotels are less than half full.

The only other fantastic deals I've ever seen were the free nights with free pass days (i.e. stay for 7, pay for 4 deals) that were offered a few years ago to create some demand after the downturn in overall travel after 2001. Since travel to WDW is up, they don't need to offer free nights and park admission anymore to fill their rooms.

Periodically, they still do some promos with decent room discounts or pass upgrades, meaning pay for a basic pass but get the parkhopper and fun-n-more features free. The room discounts on these promos can be good, but limited to certain resorts or room categories on certain weeks. Sometimes it's just the pass upgrade that they offer, which really isn't a huge savings, but it helps.

These are the U.S. deals, I know they offer similar programs for overseas guests.