Well, one thing you can look forward to is the fact that Indiana like Michigan, Ohio and Illinois is set up in a grid system. Roads run North and South or East and West. Generally there is a road grid 1 mile apart in the country. Of course, paved roads are often 3 miles apart. But these states have really great rural road nets which makes for superb cycling during the prime riding months from May till September.

I am not that familiar with Fort Wayne. But there are two multiday rides in Michigan (just a bit to your north) that you might think of trying. There is the Shoreline Bicycle Tour which is a bit laid back but it has very nice scenery. This one follows the shoreline of Lake Michigan. And there is DALMAC put on by the Tri-County Bicycle Association in Lansing MI. DALMAC has 4 day and 5 day option and a quad century. It goes from Lansing MI to St. Ignace just over the Macinaw Bridge.

As for the cold, well it isn't that terrible. When I lived up there, I used to ride through the winter. You just need the proper clothes.