I'm just looking at your route. That should be a really neat trip. We quite often do Oshkosh via Drummond Island to Carp airport (near Ottawa). Sometimes the headwinds come west bound are horrible going from Ottawa across the north end of the lakes, bumps and 30 - 40kts headwinds at all altitudes. So make sure you allow enough fuel for that. On the other hand, sometimes I've had a 230kts ground speed going the other way (in a C180!). Very nice
Drummond Island is really pretty, but the fuel is a bit pricey, and it is a car garage, not an FBO, so their hours & facilities are not what you would normally expect for an FBO. The USCBP folks are very nice & friendly tho', as are the garage folks. Sault Ste Marie (US side - KANJ) is a really nice airport, with a great restaurant 5 mins drive/10-15mins walk from the airport - Abner's - great home cooking and nice staff.
I've stopped in Chippewa County once, folks were perfectly nice, but it didn't give the impression its really set up to handle GA. The nearest buildings seemed to be prisons... The only appeal for me was the fuel stop as Drummond Island was closed by then (thanks to sucky headwinds....)
We stayed at Gore Bay, Manitoulin Island last year and the folks there could not have been more friendly and hospitable. Great place to stay. The airport manager has a Cub on floats he flies to Oshkosh every couple of years. Not much near the airport, but we were camping so that didn't matter for us. At that point, they didn't have the internet, which was causing us problems with e-APIS. As we have got to understand the e-APIS system better since then, we would be ok another time.
If you have to make a stop near Ottawa, Carp is really nice. Very helpful FBO folks there. Give them a hard time from me for not getting to AV - they promised to come last year
You might consider coming down over Door County (Sturgeon Bay etc)? Washington Island has a lovely grass runway, but no fuel. The local EAA chapter keeps a van there for pilots' use, just put petrol in it. And they have a great support set up for AV travellers passing through - I think they hold a Fish Fry the weekend before - check the EAA calendar.. Ephraim is a lovely airport, also great support from the FBO, and Sturgeon Bay ditto.
I don't know Menominee so well, but Escanaba is a great airport, with helpful staff, a courtesy car and self serve fuel.