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1.) Wifinder is a good site to find public wi-fi hotspots, and people can submit them as they find them during their road trips.
2.) Getting a wi-fi detector is an easy way to find a hotspot, because not everyone posts a sign that says that free wi-fi is available. There are a lot of companies that offer signal detectors. For example, the Mobile Edge MEASL1 is on a keychain, which is a good way to find a hotspot and measure signal strength when stopping in new towns along the way.
[Photo: Flickr | Florian]
Sometimes an encrypted connection is free for customers, so getting internet access might be as easy as stopping in, buying some coffee-to-go, and asking for an access code. Test out the connection in the lobby or hallway before actually switching rooms.
[Photo credit: Flickr user dana~2, used in accordance with Creative Commons]