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Green Bay to Indy via UP of Michigan

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We are going to a wedding in Indy mid-October. We are going to fly in to Green Bay the Saturday before and make our way across the UP of Michigan and down to Indy. Any suggestions for places to go and suggestions on how long to stay in eac area would be great. We love B and Bs and would like to stay around the $100/night range. We are two gals in our 30s - not in to the party scene but love nature, theatre, and local places. Thank you so much!

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