Some tips about my hometown:
Heading to Hurley (just across the Wisconsin border from Ironwood) takes you to the Bell Chalet (aka The Liberty Bell aka Fontecchio's Bell Chalet), my choice for eating in the region. The thin-crust pizza is marvelous (the sausage is a local recipe), the pasta and gnocchi are generally homemade and tasty (if you don't mind Italian-American style w/lots of red sauce), and the supper club-style food isn't bad. The drinks are well mixed (brandy manhattans are a local favorite), and it's a very friendly joint that brings together locals and vacationers. If you're there in winter, though, be prepared for long lines of out-of-towners.
For lunch you should consider the Joe's Pasty Shop in Ironwood on Aurora Street. One of the older pasty joins in the UP (1946), and they're VERY good -- entirely legit. I've been known to bring coolers full of their frozen pasties back to Chicago....
Hurley is an old red light district, with many bars along Silver Street and an old Chicago mob-prohibition history. The Hurley Coffee Company, on Silver Street in the old Trolla's Market (I believe that Mr. Trolla was the source of the aforementioned sausage recipe) is a nice place to have a good coffee (not so common in the area), relax under the old tin ceiling, and consider what the town might have been like in its glory days.
Bell Chalet
109 5th Ave S., Hurley (just off Silver Street)
(715) 561-3753
Joe's Pasty Shop
116 W. Aurora St., Ironwood
(906)-932-4412
Hurley Coffee Company
122 Silver Street, Hurley
715-561-5500