Friend of mine decided to go with me last minute on that sunday June 8th, conclusion = not worth it !
The space in that park is huge, but the booths over there was like half of what Market days in Chicago have, and those booths were very localized that gear towards the people that live in Milwaukee, compare to Market days gear to local crowds and the rest of the country, a much larger audience.
We got there around 12:30pm, the venue was really deserted, very few people were walking around, not sure if all the guys were partying hard the night before, but with Market days, even during the early part of the day, it already has quite many foot traffic and get crowded by mid-afternoon. There are not much to look at so we had decided to exit the venue and walk across the bridge to the man made island park instead for some views of the lake. By the time we walked back to Pridefest around 3pm, it finally gets a little more foot traffic, but there was hardly any people watching or cruising at all (don't even have any hot guys, no shirtless guys, no guys wear nothing but underwear) , so we had decided to leave by 4pm.
On the way back we stopped by the Pleasant Prairie outlet mall, got some good deals at the Crabtree & Evelyn, Yankee candles, Corningware Corelle, then went to Golden Corral at Gurnee for dinner.
The day pass is at a steep $16 compare to suggested donation in Market days (which means free). So all in all if you are going to the Pridefest in Milwaukee alone, definitely skip it, if you can make a day trip like us then it is not a bad idea.