It's part social network and part number cruncher. The free version is fine, the paid version gives you bells and whistles you don't really need but are cool. It helps to motivate me when I see everyone putting out big numbers.

There is a Plus 50 club, has around 70-80 members I think. It is "centered" in Louisville, KY. The code is 1952.

You'll need some GPS system to upload data. The phone based systems are very easy, Garmin units aren't much harder and are more accurate when it comes to elevation if that's important to you.