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I'm not really sure what else to call it, but my goal basically is to create various locations on a map and have them connect with a curved progress bar-like line.

Like this: Sample

I'm familiar with the pen tool and how to make curved lines, but I'm not really sure how to go from a curved line to the picture above.

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this is called a 'pattern brush', you define (or pick) a pattern and apply it to a path as a stroke. Google 'pattern brush' and you'll fond lots of ways how to make and apply them. –  Vincent Apr 2 '14 at 10:12
Thanks for the suggestion Bakabaka, but I believe Pattern Brushes are only for Illustrator, no? I'm specifically trying to do this in Photoshop :) –  smaili Apr 2 '14 at 11:01
Oh, I didn't see, please specify in your question. You might be in for a toughie, then. The entire image screams 'vector' to me, and I'm not sure you can reproduce the effect in Ps somewhat easily. –  Vincent Apr 2 '14 at 11:05
Sorry for the confusion. I've updated the question :) –  smaili Apr 2 '14 at 11:30
You can't do this easily within Photoshop. However, it's fairly simple in Illustrator. –  Scott Apr 2 '14 at 17:10

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