This is the best street fair/flea market/whatever I've ever been to, ever. And I've been 6 times now. It never gets old. If you like art, jewelry, chotskies, clothing, music, or just good food - GO!!
At the top of the hill, by the school, is the main part of the market, but the part down by the park, along the street, is the best part, and there are more vendors down there. You can find everything there - hammocks, baby shoes, musical instruments, coca leaf tea, calendula soaps, art, etc etc etc...
Over by the mall (at the end of the street) is another portion of the market. There is a lady who makes stuff out of bamboo there at great prices, and another lady sells coffee and makes Virgin Mary dolls out of corn husks. It's amazing.
The food - first of all, Usaquén is the gastronomy capital of Bogotá. I highly recommend most of the restaurants, especially 14 Inkas. Best. Ceviche, EVER. Second, the street food at the market is great. There are always people selling grilled corn, in the converted parking lot, there is a vendor that sells cupcakes and chocolate covered strawberries. Up on the hill, you can usually find food trucks, fresh fruit, and other sweets. Sweet Cacao is a chocolate vendor who is there sometimes - AMAZING chocolates. Also Late Mi Chocolate has been there every time I've been. Try the chocolate covered nuts and bananas. Everyone will give you samples :)
If you want to see live music, hang around the park by the church. Many times singers will come from the coasts and do salsa. People dance in the streets. It's great. Other musicians can be found along the street with the vendors.
You don't need to speak Spanish, but know your numbers.
Point - ask "Cuántos hay?" (how much?) - and remember if you look like a tourist, they've upped the price. Haggle. They will make a deal with you.
If you need to differentiate between several things, point and say "este" (this).
Bring cash - most vendors don't accept cards.
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