In Kenya I would go to sidewalk sales like in your picture. You can find many things that are nice. Here in America in my own area of the woods I like resale shops, flea markets, and yard sales. Sometimes a storage shed sale as well.
I have been to some fairs but I normally tend to avoid them unless I am with others.

In NE we have many state fairs in NH, MA and VT: Have attended:

VT- Essex Jct
MA-Brockton Fair, Barnstable County Fair
NH, Hopkington Fair, Deerfield Fair, Stratham Fair, Hudson OldHome Days

We have many flea markets I've perused or setup withfriends: Londonderry, NH, Amherst, NH, and Northfield, MA
In summer have weekly food market in every town including my own Merrimack,NH.

I like the medieval fair. Lots of interesting food, gifts, comedy skits, jousting, ogres, bar wenches and you can dress up

Usually flea markets and garage sales. I don't care for large events since I don't care for multitudes

what is roasted gyros?

Flea markets..I love them..I miss "junk" stores though..

I enjoy/ed ‘manning the Democrat's booth’ at local fairs and ‘Whatever Days.’ In a smaller county, with fewer such days.. I still enjoy meeting the locals ..if from the other side of the booth

Not much for parades, our local Fourth of July event was ..memorable. From horses in Oregon - to hillbillies in Appalachia, the adventure continues

Glastonbury - I love it!

The one I really look forward to is the Ren Faire in summer! So much fun to dress and be silly for a day, see performances, and presentations.
We also have an art festival/sale in the fall that is a place I like to go.

You're from Louisville? My father's side is from there. Small world

I go to boot sales (flea markets) several times a week . This combined with weekly and monthly auctions keep me busy most of the time .

Any outdoor event or festival where we can play. I LOVE playing music in the street. In England that tends to slow down a little for a big chunk of the year but springs coming and I've got my box ready.....