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We got a 27 foot trailer and a car to park somewhere overnight safe? Comin from Chicago, any suggestions ?
 

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I like the North Corridor Trail that parallels Hwy 2, its big, passes through a lot of towns, and has dozens of off trails to explore. I have ridden it a lot on ATV in summer, it would be a blast on a sled. Plus, you are right near Lake Superior, so lots of lake effect snow.
 

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I have stayed at Donner's Bay, Mercer Wi, They have 6 cabin directly on the snowmobile route. Treated us great and have gas so you can start out your ride right. I will be there again this winter. 1 thing I should meantion is they have been real good about calling if the trails aren't very good, so I could plan accordingly. Worth a try.
 
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