Suggestions Regarding Roadtrip from Milwaukee to Niagara Falls

If you're thinking about visiting the area surrounding the great lakes I would suggest crossing at Niagara Falls but not spending too much time at the falls themselves. Niagara Falls is somewhat urban but really tacky. I would suggest spending time in Niagara-on-the-Lake which is the centre of wine country in Southern Ontario. There are great hotels, inns, B&Bs as well as theatre and great restaurants. Peller Estates and The Charles Inn are my favourite places for dinner. The wine route winds all the way up to a town called Grimsby just before Hamilton. Stick to the smaller wineries like Thirty Bench, Angels Gate or the underground Megalomaniac http://winecountryontario.ca/ Wineries like Angels Gate or Vineland Estates have a great lunch too.

Since you've got 10 days you can drive to Toronto (2 hours from the border) or if you're really feeling adventurous I highly recommend the Muskoka area in July/August (4.5 hours from the border).