I spoke to Ella on the Monday ride a bit. I don't have much else to add (you'll notice that doesn't stop me from chiming in, though
).
We have only stopped on the way through Ashland after
Ole's ride Up North in June 2010. (I can only recommend the Hardee's for fine dining!)
We've had great riding about 60 miles to the southeast in the Minocqua / Eagle River area. Hayward to the southwest is also very nice; you may want to plan a route around some lakes there on the route to/from Ashland. No matter what, we've enjoyed most every road in northern Wisconsin and the UP. You'll have a blast. Be sure to post pictures when you get back!
Anyone else have some actually helpful info for the Ashland, WI area?