It looks as if your "dashed" stroke isn't a dashed stroke but as row of separate non-dashed ones.
Your Layer panel seems to show this too. Turn off the preview and this is almost definitely what you will see.
You could laboriously join the segment ends but frankly it would be quicker to redraw the path.
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One advantage of doing what Steve said would be the option of improving the appearance of the path(s).
Thanks, Steve and Jacob.
That explains the problem I was having.
It looks like I have a bit of redrawing to do - one for each trail! Ugh...
For my small part you are welcome, Mike.
If you need a few hints to make it easier, you may (some of them touched upon in a recent thread):
1) Click the Direct Selection Tool before you select the Pen Tool,
2) Place as few Anchor Points as possible, where things happen,
3) If you drag out the Handle and find out that you need to adjust the position of the Anchor Point, you may press the Space Bar to move it round, without letting go of the Handle (you may switch back and forth until you are satisfied,
4) If you need to go back and adjust an earlier Anchor Point (Position/Handles), you can just press Ctrl/Cmd while you are at it, and continue where you were.
I can't remember if that was possible in previous versions but using CS5 here's what I did:
1. I created a freehand random path with the Pencil tool and with the Eraser tool I put some gaps
2. Selected all, which can be done with any of the selection tools including the Lasso tool and used (Ctrl/Cmd + J) Object > Path > Join
3. I reduced the anchor points of the new path with Object > Path > Simplify.
Thanks for those handy tips!
Part of the problem is there are long gaps between my uses of AI and I
often feel like I am starting from scratch.
You are welcome, Mike.
... there are long gaps ...
Apparently longer than those in the paths.