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Making my own virtual walking adventure?

Hello all. I asked this several months ago, but never really got an answer. But rather than reviving a long buried topic, I figured I'd make a new one.

 

I'm looking for some sort of app, website, or program that would allow me to create a virtual walking or hiking map. Basically, I'd like to be able to upload an image of a map, trace out a path on it and set the steps and/or miles to each landmark on it, upload pictures for the landmarks, and share it with friends and family to start a little friendly walking competition. Ideally, it'd be able to work with fitbit, so as you walked, it automatically adds in your steps and advances your icon on the path based on your distance.

 

Now, in my google searches, I've seen apps that do this with real world trails, but none that let you create your own like I mentioned above. Being the massive nerd that I am, I'd find it more motivating to trace my trek through Middle Earth, or walk between the planets of the solar system, or follow Mario's footsteps on his quest to rescue the princess from Bowser. Does anyone know any apps or websites that would let me do this? So far, the best I could manage is making a google docs page with the map and having everyone move their own token manually. That didn't last very long, unfortunately. Anyway, thanks in advance!

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You might try looking at Stridekick.com. You can either use their premapped 'Journeys' or a 'Target' challenge. With the 'Newsfeed'  feature you could post your own maps (though not interactive) and corresponding pictures that are seen by your friends.

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