I'm going to be busy accumulated and posting Florida Trail Heads, so I won't have time to do this. However, I had project idea if you're looking for something to take on.
This assumes you don't want to do another state's trailheads. It would be cool if you did, but given the numerous data sources you'd need to look at, I can understand why this might be a bit much.
The American Volkssport Association (www.ava.org) organizes walks, bike rides, and swims around the United States. (I'm sure there's an equivalent Canadian organization.) While most of these events are one day events, there are also a series of "Year Round Events" scattered around the United States.
For example, in my home town there are both a 6K and 11K walk which start at the Public Library. It might be interesting to have a POI file which included all of the YRE's in the United States. Since they can change every year, the file would need to be updated on a regular basis. However, the project shouldn't be all consuming.
If you're interested, the information for the events can be found on their web site.
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