We would not do #1. We have done Highway 14 from Fort Collins to Walden then down to Granby. It is a good road for towing no real steep mountains and sharp curves. Don't know about 14 from Walden to Steam Boat springs. Maybe Ron Ames will come along and give you info on that.
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Paul and Jan Kelpe
2014 Big Sky 3150RL
2015 GMC Denali, Duramax/Allison
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