All the yolking about hating/loving Hamilton aside, it's a city with a lot of highs and some lows. Most see it from the Skyway, which naturally showcases the most obvious downside, but the industry of Hamilton is a big part of why I love the city so much. Everyone needs steel (especially in this era of trade wars!), or the myriad other products made in Hamilton, and I'll take a factory and blue collar folks over yet another Toronto office and condo stocked with marketing managers and brand consultancies.
The downtown core could do with some rejuvenation, but you don't have to go far to find all sorts of cool stuff, and a city full of the friendliness and mutual support that often comes from places where people have less rather than more. If you want a young vibe and good food, James North is a good place to start, especially if there's an Art Crawl on. Rapscallion, Born & Raised, Martello and Le Tambour are all highly recommnended. Locke St has all the yoga mom vibe you could hope for, and then Ottawa N has a really interesting mix of old-Ham blue collar (textile district) and new-Ham cocktail bars and tapas places. Gage Park has a small tropical greenhouse and some sort of ethnic or music festival pretty much every weekend through July and August.
Then you've got the classic places
@crankcall suggested (though the Connaught is now condos I think, as is the modern way), all of which are excellent and worthy of a visit in the west edge of the old city. Beyond that, there's the quaint and sedate town of Dundas next door, plus lots and lots of hikes and waterfalls along the escarpment. Highlights would be Tiffany Falls, Felker's Falls and Devil's Punchbowl (if it's flowing). Oh, and Starlite Drive-In is still going too. Maybe better later in the year on a motorcycle, though, to dodge the bugs...
