Dear Fastrog -
I will not lie to you.
There are many times on tour that I suspect I need my head examined.
But - - -
The bad times beget the sublime moments that make it so worthwhile.
Give yourself time and I am sure the Red Sea will part for you.
Perhaps not now, not next week - but eventually.
Kentucky can be tough, too. Enjoy the Baptist Church hostel in western Ky - great folks who run it.
Missouri can be tough, also. Kansas and eastern Colorado can stretch endlessly - and bake.
(Gawd, this guy is really a bummer, no?)
Then you save dessert for last. The Colorado Rockies are stunning - and you will be super fit by then.
If you can, give yourself a little extra time to enjoy Grand Teton NP - camp at Jenny Lake and hike a bit.
In Yellowstone, consider looping via Lake and Canyon rather than the direct shot from West Thumb to Madison.
Ride early to avoid traffic - great hiker/biker campsites, esp. at Canyon - the Grand Canyon of the Yellowstone is worth it.
The mountains aren't as high in Montana, but the wide open spaces and sparkling air are worth the wait.
And Missoula is simply the super-dooper-est college town in the USofA.
Next up - Idaho - seriously try to camp near, then soak at Jerry Johnson Hot Springs. Across the pack bridge.
And the rugged canyons of eastern Oregon are really sweet - consider the route via Smith Rocks State Park.
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East-to West is hard - esp. starting in June. Hot, humid, grueling.
Just keep plugging away - you can do it.
Slow down, smell the petunias, and if you are frazzled - - stop for a long break or for the day.
I don't care whether you ride 29 miles or 92 miles. But 92 miles can make for a really grumpy cyclist.
Give yourself permission to wing it and have fun. - - Jama