I attended Speedwire's holiday party last night, at O'Lunney's off Times Square, and on my way to Penn Station passed through Times Square. I decided to give the free Yahoo sponsored network a quick whirl and found it to be a good experience. Easy to connect to through a sea of SSIDs, the only nit I had with it was the non-mobile friendly initial T&C page. I've got three screen shots for you below, T&C, welcome, and redirect. Kudos to Marshall Brown's Wiredtowns for getting the deployment business and executing well.
Another essential component to marketing outdoor networks is making their presence known to non-geeks and occasional visitors. Outdoor advertising such as these lightpole banners shot by Scott Beale drive awareness and usage.