Flea markets are good ideas, that pretty much goes without saying. Although don’t you hate it when a flea market looks like it’s going to be really great and it’s really crappy and thus a major letdown? For the most part, the Woodstock flea market is crappy (that is, if you share my taste in all things art, fashion, etc).
However, if you ever find yourself at the Mower’s Market be sure to hunt down Marlene, she’s awesome and has super awesome stuff. My flapper hat is a Marlene find from a few years ago. Shall we take a moment to reflect on the radness?:

Good idea: Make food for your favorite vendor because she’s your favorite vendor and you like making food for people. Because your mother is part Italian, definitely go overboard.
White bean and roasted tomato galette:

Allspice roasted butternut squash:

Sauteed kale + shallots:

Mediterranean spelt salad:

Mostly every other vendor sells, well, Woodstock-y stuff, which is fine if you learn to except it for what it is and only take the quickest glance at it. There are some exceptions to this rule, though. See below.

Good idea:
Always, always, always take a quick glance around the whole market, even if you’re itching to get to the Woodstock Library Sale. Score boxfuls of vintage hats for $5 each! Ignore obnoxious people who take interest in said hats only after you start looking at them.

Add to your ever growing collection of hats.

Oy, I’ll have you know that was a low point for my room. It looks a lot better now, thanks.
Also, that’s not how you should store your hats, don’t follow my example.
Also, that’s not even a quarter of the hats I own. I should just open up a store already.