Hi Alisa!
Generally speaking, both are great times to visit Walt Disney World. For both May and October, the weather should be cooler than it will be in the middle of summer. The crowds will also be lighter.
Between the two, however, I recommend coming in October. That's because of two special events that will be available in October:
- Mickey's Not So Scary Halloween Party
- Epcot International Food and Wine Festival
Mickey's Not So Scary Halloween Party is a hard ticketed even in the Magic Kingdom. Guests can go trick or treating while in costume and there are special activities, including a spectacular fireworks show and the outstanding "Boo To You" parade. The special fireworks show and parade are my favorite at Walt Disney World. Since it is a hard ticketed event, you will need a special party ticket to get in; depending on what night you go, the crowds can be substantially less than on a normal night.
The
International Food and Wine Festival is a lot of fun. There will be extra food booths set up throughout World Showcase in Epcot where you can try regional foods, wines, and beers. There will also be special parties and demonstrations that guests can attend. Come hungry!
A resort with easy access to both the Magic Kingdom and Epcot is the Polynesian Resort. It's on the monorail line giving you direct access to the Magic Kingdom. It's also within walking distance of the Transportation and Ticket Center, so it would be possible to walk there and get directly on an Epcot monorail. Most young guests absolutely enjoy the Polynesian, especially its volcano pool.
Enjoy planning and write back if you have any more questions!