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A single Access Point can be reached from a distance of no more than 100-200 meters (300-600 ft.), but there also exist Hotspots consisting of hundreds of Access Points which cover entire Airports, Hotels, or even Cities.
In order to connect to a hotspot, you will need to get an IP address. In nearly every situation, your computer will do this for you automatically with DHCP. If you switch between different networks (wireless or otherwise), sometimes your computer may continue to use an IP lease from the previous network. In that case, you have to manually release and renew the lease. With Windows, you can use the ipconfig and winipcfg commands to interact with DHCP.
If you connect to a hotspot and get an IP address, but you are not able to reach other sites on the Internet, you may need to register with the provider. To log in, you need to open a new web browser window. Once you try to visit a website on the Internet, your HTTP request should be redirected to a page where you can log in. If you're not already a member of the specific hotspot provider you will have the opportunity to sign up.
Once you have signed up and logged in you are all set to utilize the hotspot!
Here are just some of the many sites out there:
Here are sites that focus on Metropolitan Areas:
Special thanks to GeekNJ, justin, lilhurricane, NewYorkerTom, fire100 and julio for their contributions to this FAQ.