He do know them pretty well.
Mountain bike or road bike?
Westbound or eastbound?
There are actually 3 paved options - from N to S - US 14A, US 14, & US 16.
Eastbound, US 14A is brutal - left me gasping for air on every switchback.
Been up it twice, down once and practically burned out my brakes.
US14A provides access to the ancient Native American Medicine Wheel.
US 14 heads east thru Shell Canyon which is lovely but narrow.
It tops out at Granite Pass - the lowest of the three crossings.
US 14A merges with US 14 at Burgess Jct.
The downhill is a screamer which has spectacular views out into the Plains.
From Sheridan you should continue east on US 14 joining US 16 at Ucross.
There's a little store in Clearmont and bars at Arvada and Spotted Horse.
Heading to Ten Sleep there is a paved road from Manderson via the Nowood Valley.
US 16 heads east thru the spectacular Ten Sleep Canyon - truly magnificent.
You top out at Powder River Pass - almost 10,000 ft.
There are three segments east of the pass.
First a 9-mile moderate (6%) downgrade, then 12 miles with seven ridges,
Then a 12-mile moderate (6-7%) downgrade into Buffalo.
From Buffalo is may be tempting to take I-90 but that is a grave sin.
US 16 is longer heading to Gillette, but quite nice - esp the first 20 miles.
Mid July may be a little late for the wildflower display.
Nowhere in the West are there more beautiful wildflowers.
Knee-deep fields of every color - usually late June to early July.
There may still be some good areas at high elevation later.
Because the Bighorns have so many natural meadows - views are fabulous.
US 14A has no services, US 14 some - esp Burgess, US 16 the most.
All have plenty of campgrounds plus free camping anywhere.
It can snow any month of the year.
If you have wide tires, consider heading down Crazy Woman Canyon.
It's off of US 16 just after the 9-mile section east of the pass.
(It also saves you the 7 ridges - but means 12 miles of gravel.)
you come out on Hwy 196 (Old US 87) 12 miles south of Buffalo.
I'm partial to US 16.
Even though Power River Pass is higher than Granite Pass,
You drop further on the east side to Dayton than to Buffalo.
So you have to climb over a ridge east of Sheridan on US 14.
The seven ridges on US 16 are easier eastbound since each one is a little lower.
Ten Sleep Canyon is awesome - alone worth doing US 16.
You can climb it via the old highway on the south side (unpaved) but shaded and no traffic.
If you did that, you get the full expanse of the canyon views, too.
Whichever way you go I strongly urge you to spend one night up top.
It's just too beautiful up there to miss.
There are a couple of places where you can do a short wilderness hike, too.
Lemme know what your plans are.
Not sure if I'm going to be in Buffalo this summer.
If I am, you are welcome to stay.