Having grown up and lived in the Detroit area, I have been to many Woodward Dream Cruises since the very first one. The cruise itself is technically only on Saturday, but the event has become a 2-week draw with global attendance. Every night leading up to the actual cruise there are car group gatherings at various local establishments. Dugan's Irish Pub on Wednesday before the cruise was the unofficial official Corvette gathering where you could surely see every single year of production represented in the parking lot. I recall when the PT Cruiser was a fad, over 200 gathered in one parking lot one night of the week. It is one of the most ridiculous and cool car events one can attend. The car show goes 2-3 blocks deep either side of Woodward for about 17 miles!! Nearly any car from any era can be found on display along Woodward during this timeframe, if only there was enough time to see them all!
For sure I do not recommend trying to actually drive on Woodward on that Saturday, in ANY car. It is not enjoyable in the least and the road is clogged up by many tourists and families in minivans, it is not just the kind of cars you want to roll with. Do you want to be in the parade or do you want to watch the parade? Saturday is better for hanging out under a canopy on the side of Woodward with a cold one and watching traffic roll by. And wandering up and down as far as you can stand to walk to see the amazing collection of cars parked up and down every side road, back alley and parking lot. Many bleach soaked side roads for burnout exhibitions as well.
Having the Gathering there this year was a great idea, the variety of car related things to do in the immediate vicinity of Woodward and then around Detroit itself pretty much guarantees you'll thoroughly enjoy yourselves.