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We also would take Berthoud Pass, exit 232 off I70 if you are coming from Denver. The pass is mostly 3 lanes now, with uphill passing lanes. It is very comfortable towing on the pass, as long as you are OK with winding roads. The roomy switchbacks and pull-offs for downhill travel make it much easier traveling than several years ago. I use my E-brake for more easier travel. If coming from the west on I 70, then Rte. 9N is probably your best option. That route will alleviate the Eisenhower Tunnel and Berthoud Pass. This route also has no major hills.
As far as going to South Dakota, we prefer going 34 South to Granby, North on Rte. 40 to CO-125 N to WY-230 E. That takes you up to Laramie and you can then plan your route to South Dakota. The roads are narrow, but usually very empty & beautiful scenery. There is even a free public hot springs in Saratoga, WY, a must for us as we pass through.
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