TL;WR

Eating and drinking and working.

Great culinary experiences are defined not just by the food - but by the space and the people. One of Waterloo's greatest treasures is Sonny's Drive-In at 256 Weber St in Waterloo. Pre-kids, we'd make our way there after a night out - hoping the onion rings would make the morning a little easier. Today, I take my kids there for a post softball hamburger. If you haven't been, you should add it to your list.
What to do.
The air around Victoria Park will smell of BBQ thanks to the annual Craft Beer and Ribfest. It runs Friday afternoon through Sunday afternoon. Personally, I always go for Ribs Royal. There are twenty craft breweries to try too - so take the bus or a RideCo.
Don't forget that the City of Kitchener is offering free bike checking at RibFest. The Record has an article with details.
The folks at TWB Brewing Cooperative (300 Mill St, Kitchener) are having a customer appreciate day this Saturday, July 16 from 11-9pm. There will be free hugs too - read it right on their Facebook page.
A little brain melting, a little skull raising, and a great night of music -- experimental and genre-bending, but still accessible and, frankly, entertaining to the extreme at Open Sesame. Friday night features FASTER and Dave Gould. Doors open at 8.