Has the FREE DDP ever been offered in Feb or Oct?

Well, in 2005 (the first year of the Free Dining promo), we checked in on October 1st, and had Free Dining for our 7 night stay. The promotion ran through 10/2, I believe, so there were folks who could check in on the 2nd and have Free Dining through the 12th (if they stayed the max # of nights- 10).

That was the only year the Free Dining start dates went into October, I believe. The Free Dining hasn't been offered any other time of year- just late Aug- very early Oct.
 
No, it's generally only offered for end of August and September. This has been typcially a slow time for attendance and therefore they run this promotion to increase bookings. February is a peak travel time, from the 15th through mid April is one of the busiest times at WDW due to President's Day, Mardi Gras, Spring Breaks and Easter. These are prime times when school systems take their breaks. Our schools are closed a week at President's Day and another week in April for Spring Break.
 













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