Gambling is one of the more popular reasons to cross the border. Windsor has six casinos and bingo facilities, including one within a racetrack, Windsor Raceway.
There are 11 wineries in southwestern Ontario and one a bit further on Peele Island, Pelee Island Winery, which is still under 90 minutes from Detroit. The wineries all have tastings; be sure to have a designated driver. There are also a number of cute bed and breakfasts in the region.
Colasanti's Tropical Gardens has a full day's entertainment; there is a petting zoo, indoor miniature golf, kiddie rides and an arcade. There are seasonal activities like pumpkin painting, apple festival and a haunted maze.