Appreciated any pro and cons for this trip route.
Been via rt 80, looking for something new but concern about the weather in Rockies during TG week. (Like historical significent of rt 50)
Will drive Landrover with U-Haul trailer.
Total days planned - 8 (eight) to complete this trip.
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There is something intrinsically enticing about following a specific road over vast distances, especially when those roads are 'street level' highways and not sui generis Interstates. Many years ago, in fact, National Geographic magazine did a number of articles that documented trips just like the one you are proposing: follow a US route form (near) one end to (almost) the other. Such a drive will certainly give you a good feel for the various regions you'll be traversing, and US-50 includes a number of stretches and towns that are worth exploring including the "World's Loneliest Highway", Arches National Park, Colorado National Monument, the Black Canyon of the Gunnison, Dodge City, Kansas City, St. Louis, Amish towns in southern Indiana, and mounds built by Native Americans 2000 years ago in Ohio.
On the down side, under the best of conditions, driving on these 'street level' roads is inherently slower, with lower speed limits, towns, traffic and stop lights. With a decent sedan and driving 8 hour days (plus stops) it would take you about 6 days to complete the drive, even cheating by using freeways through or around the major cities. In addition pulling a trailer is going to slow you down even further, especially as you cross the Rockies. I think you should count on a minimum of 7 fairly serious driving days. That only leaves you a single day to parcel out among all the sights to be seen.
So if you commit to this, it will have to be with the realization that it will have to be all about the journey. But although that is the case, I wouldn't be overly concerned about weather through Colorado. It is possible that you will be delayed by snow, but if that is the case, then you can always use Interstates for the eastern portion of your trip and make up some of the lost time.
AZBuck