DAY 1
ITINERARY
CHICAGO to NORTH DAKOTA
Rolling out of Chicago at 10 a.m., the drive began with a simple direction and no real destination beyond distance itself. the goal was northward into open space, away from buildings, traffic, and anything that felt familiar. The city slowly unraveled into suburbs, then suburbs into farmland, and eventually farmland into a kind of quiet that stretched all the way to the horizon.
Hour by hour, the sense of time started to dissolve. Small towns blinked by, gas stops came and went, and the landscape flattened into long, uninterrupted stretches of road and unblemished sky. By the time North Dakota appeared on the map, daylight had already faded into a deep, early darkness.
Near the state line, a quiet roadside pull-off in a nameless town became the stopping point after roughly eleven hours on the road. With no reservation and no urgency to find one, the car became an improptu shelter with seats folded down, windows cracked slightly, and the vast silence of the plains pressing in from every direction. Sleep came easily, carried by exhaustion and the stillness of a landscape that seemed to go on forever.
DAY 2
Tagline
TEDDY ROOSEVELT NATIONAL PARK
Departing the roadside lot at around 7 A.M., the journey continued west on I-94 through open prairie and an uninterrupted stretch of road. The North Dakota landscape seemed endless except for the mall towns that appear briefly and then disappear just as quickly in the rear view mirror.
But by noon, subtle changes started to take shape. The flat fields gradually gave way to rolling hills as the first hints of the badlands appeared. By the time Teddy Roosevelt National Park came into view, the transformation was complete. The prairie had fully surrendered to dramatic "painted" cliffs, winding roads carved into the land, and deep, sculpted cuts stretching in every direction. The scale of it felt immediate and overwhelming.
The afternoon was spent moving slowly through the park loops, stopping at overlooks where wild horses drifted through valleys and bison crossed the grasslands without urgency. The silence carried a weight of its own, broken only by the howls of the wind.
As evening settled in, the last light spilled across the jagged, multi-colored canyons in warm gold outside Medora, ND. Dinner was in the form of "Pitchfork Steaks" which were cuts of tenderloin steak, skewered on a pitchfork, and dunked in a giant cooking vat. Afterwards, from a small Airbnb, the badlands softened into shadow, and the entire landscape slowly dissolving into quiet, expansive night.
DAY 3
MAKOSHIKA STATE PARK
Pulling out from Teddy Roosevelt National Park in the early morning light, the badlands were still quiet and the roads almost empty. After about an hour driving east, the border of Montana came into view. The welcome sign of Glendive, MT, featuring a dinosaur's skeletal remains, was an exciting sight. Today would be fossil hunting day at Makoshika State Park.
Arriving at Makoshika feels like stepping into an exposed, prehistoric version of the earth where time has stripped everything down to layered rock, deep canyons, and open, wind-carved badlands. Just outside beautiful Glendive, the park stretches across rolling, rugged terrain filled with fossils, hoodoo rock formations, and winding hiking paths that cut through the landscape like veins. The silence is out there is only matched by the intensity of the July sun. Be sure to bring plenty of water and sunscreen.
After a couple hours poking around in the dirt for fossils, and finding nothing, it was time for lunch. Following a quick burger at McDonalds, the road trip continued southwest towards the border of Wyoming and into the vast forested area of the Yellowstone National Park.
The most scenic route goes through Billings into to Red Lodge, before ascending over 10,000 feet to Yellowstone's Northeast Entrance near Cooke City. This route is known at the Beartooth Highway, or U.S. Highway 212, and climbs 5,000 feet through dense pine forests leading you to an enchanting world of alpine lakes, glacially carved cirques, and vibrant wildflowers. The highway connects the towns of Red Lodge, Montana with Cooke City/Silver Gate, Montana at the northeast entrance to Yellowstone. The Silver Gate Lodge served as a quaint and rustic accomodation for the night, complete with fishing gear to use in the nearby river, and firepit to grill your catch on.
DAY 4
DAY 5
DAY 6
DAY 8
GRAND TETONS
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DAY 9
Tagline
THE DEVILS TOWER
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DAY 10
Tagline
ROADTRIP BACK TO CHICAGO
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