Western Adventures: Across the Wyoming Line

Wild Open Wyoming.

June 4th 2022:

Crossing into Wonderful Wyoming – The Cowboy State

One of my favorite sets of scenic drives in the USA is the road from the edge of Western South Dakota onward to Yellowstone via I-90 to Highway 16/14.

Before I continue my travelogue from June 2022, I wanted to give you a window into the different paths the Black Hills into Yellowstone Country.

I’ve traveled the journey from Mt. Rushmore and to Yellowstone several times, each with a slightly different byway. The western Black Hills that sliver through eastern Wyoming is rugged and wide open wild. The plains roll out like eternity against the endless blue sky….the dark ‘Black Hills’ like craggy shadows on the horizon.

It is the sort of country you can get lost in and find a peace in the freedom of the vast beauty. I find myself turning deep into prayer – talking to God as a friend in the Wyoming frontier. The prairie plains against the buttes and distant formidable mountains is the intersection of heaven on earth.

Choose your own adventure from SD to YNP

If you are planning to trek from Mt. Rushmore/Black Hills to Yellowstone (or from YNP to SD) you have several options and each road will take you through gorgeous scenery. I’ve laid out a few options below, but each can be tweaked depending on your time and sightseeing goals


If you want to enter Yellowstone via the North or Western Entrances (*note the Northern Entrance will hopefully reopen in 2023 after the catastrophic flooding on the Yellowstone and Gardner Rivers) you can head west on I-90/I-25

I did this route in 2005 during a cross-country 10 day drive. While you are on the interstate, stopping through Buffalo and Sheridan on towards Billings, you still experience the western feeling of a high lonesome drive.

This route will enable you to stop for a spell in historic Sheridan and the lovely Historic Sheridan Inn. Built in 1893 as an investment of the Sheridan Land Company and Burlington and Missouri Railroad, in a partnership by Buffalo Bill, The Sheridan Inn became a premier hotel in the west. For a time it was the only hotel to have electricity between Chicago and San Francisco. The historic inn was designed by architect Thomas Kimball who modeled it after many of the hunting lodges in Europe and particularly Scotland. To book a reservation at the inn click here

From Sheridan you head north into the Crow Reservation. One of the most beautiful and desolate roads in Montana, this stretch of highway gives you a glimpse into the land of The Crow tribe. I have a great respect for Native American culture and The Crow are a fascinating peope. They call themselves the Apsáalooke, “Children of the Large-Beaked Bird” — encompasses over 9 million acres in southeastern Montana.

The Chief Plenty Coups State Park is a great place to learn about The Crow and their people.

It is also in this stretch of arguably the most beautiful scenery in the world you’ll face the bitter human struggle in war at The Battle of Little Bighorn.

I strongly recommend stopping at this important battle – where Crazy Horse and other Native Americans fought for their land. It is where Custer and his approximately 200 men met their demise.

Stop by the visitor’s center learn about the history of Custer’s Last Stand. I always try to look at history through both sides, because war is complicated and and harsh. I was really moved at the battle site, taking time to remember the fallen on both sides. Don’t miss this stop before heading north to Billings then west towards Bozeman.

I-90/I-25 to Sheridan then detour to Highway 14 West near Ranchester

This in many ways is my favorite drive because it is a journey back into prehistoric time , winding roads, gravity-defying vistas and deep canyons. However this road is NOT for the faint of heart. It is notorious for its switchbacks and high grades. I love driving the road, but if it is raining or there is a chance of snow it is not worth the risk. This route also takes a longer time to navigate given the bends and breaks through the heart of the Bighorn Canyon.

What is extraordinary about this stretch of highway is the ability to see some of the oldest rocks in the world. Shell Canyon Falls reveals rock that is 4 billion years ago – we’re talking the dawn of time.

credit: World of Waterfalls

I-90 to Highway 16: West from Buffalo, WY

The most popular western road to Yellowstone from the Dakotas – Highway 16 – known as the Cloud Peak Scenic Byway wows stunning vistas as you navigate through the edge of Bighorn Canyon into the beautiful Bighorn Mountain Range and beyond.

The views are spectacular without the fearsome switchbacks of Highway 14.

Detour to Devils Tower:

South Dakota’s Black Hills and Wyoming’s north country are filled with hidden gems from historic towns to geological sites (Devils Tower), recreation (Key Hole State Park – Lake), and historic points of interest…The scenery is all gorgeous and it is hard to skip a mile.

One detour I definitely recommend taking is to stop in the town of Sundance, WY and spend an hour or two at Devils Tower (known by the natives as Bear Lodge). This monolith towers 1267 feet above the Belle Fourche River. Devils Tower was featured in Steven Spielberg’s Close Encounters of the Third Kind and is a desitnation for rock climbers. Fun fact: President Teddy Roosevelt declared Devils Tower to be the first National (Natural) Monument in the US.

Look for an upcoming post on Devils Tower (Bear Lodge). I did not have time to visit this trip -but have been several times and it is AMAZING…Not to mention neighboring Sundance is a charming western town packed with history.

Sundance (ironically located in Crook County) was the stomping ground for Butch Cassidy and the (you guessed it)…The Sundance Kid.

Stay tuned for more western adventures as we check out Buffao and drive into the heart of the Beartooths towards Cody, WY.

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