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Also, if i did drive, how many people would we be able to round up for a weekday trail ride vs weekend so that my sister doesn't have to take off work to ski.
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Something to consider: Skiing on the weekends is HORRIBLY crowded and traffic on I70 (the only real route to most resorts) is HORRIBLE! Skiing on the weekday will be FAR, FAR, FAR more enjoyable, and well worth your sister taking time off of work. (JMO)
On the other hand, wheeling is good anytime. There will still be more people on the weekend on the trails, but nothing that will make a significant difference in your enjoyment...can't say the same for skiing. If you do go skiing on the weekends, I suggest Loveland. Not a resort, no hotels, mainly locals, less crowded.
Ski in the week + forest service roads on the weekend = maximum enjoyment + minimal frustration.
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