You can walk from to OKW to DD easily. The walkway begins next to bulding #55 at South Point. Caskbill has prepared a full decription of this <a href="http://www.disboards.com/showthread.php?s=&threadid=160187">pathway.</a>
There are no walkways to any other areas from OKW. Any other foot travel would involve crossing busy highways, with no sidewalks or even bike paths for guidance. I have walked to PO/Riverside, but you must cross busy Communtiy Drive and then either venture out to Bonnet Creek Parkway or go thru the woods. I wouldn't suggest or encourage either option.
The DD route travels past the old DI Treehouse Villas and then on to the SSR construction area before arriving at Cirque.
Enjoy!