Here’s our itinerary and some of our favorite things along the way:
Day 1. We left in the afternoon and drove from Chicago to Sioux Falls, South Dakota. I booked the Staybridge Suites Southwest in advance – both because the hotel selection in this area is light and because the hotel was very new (especially important during the pandemic).
Day 2. We chose to get moving in the morning rather than checking out Sioux Falls, and began trekking West through South Dakota on I-90. Be prepared: this is a long, uneventful drive. We exited at Cactus Flat, and took the 39-mile loop through the Badlands National Park. The scenery is fantastic – a mix of vast expanse, desolatIon and jagged shapes. There are several overlooks that make great photo opportunities while stretching your legs. (Tip – Our road trip took us through three national parks. So, next time, we will purchase the annual national park pass instead of paying at each park.)
The loop exits back on I-90 near Wall, South Dakota. We quickly visited Wall Drug, but it was crowded (not great for social distancing) and was primarily filled with touristy trinkets. Next time, we won’t make this stop.
Mount Rushmore is located about an hour and a half from Wall. The day we visited, the central walkway was mostly closed. So, we barely stuck around long enough to to snap some photos and mentally check this American landmark off our to-see list.
After dinner, we hit the road for another long, hard drive to Billings, Montana. Even after a (very) late check-in, the staff at the Northern Hotel delivered a bucket of beers (the freebie I selected when booking our room) to our room – this was a nice touch after a long drive!
Day 3. We earmarked this day to explore Bozeman, Montana and the surrounding towns (Livingston, Clyde Park, Ennis). We were glad we did! Bozeman is amazing. Shops, restaurants, unbelievable scenery. I highly recommend MacKenzie River Pizza. Mabel even asked me take a photo of her with her macaroni and cheese pizza. After our unscheduled day of exploration, we arrived at 320 Guest Ranch for the night. Our cabin was rustic and cell coverage was limited, but the girls were thrilled to see horses up close and spend the night in a non-traditional room.
Day 4. Yellowstone National Park’s nearly 3,500 square miles of terrain provide amazing opportunities for exploring, hiking and camping. You could spend many days or weeks immersing yourself in the beauty of its geysers, hot springs, rivers, valleys and canyons. But, if you’re time-constrained, you can see the most noteworthy sites in a couple days. We allotted four days for exploring, which ended up being the right amount of time for our family.
For our first day at Yellowstone, we balanced driving with easy hikes on raised surfaces. We traveled through Norris to Mammoth Hot Springs. After adjusting to the sulfur smell, we soaked in the prehistoric-looking vistas of the Norris geyser basin and Gibbon Falls.
We stayed about forty-five minutes North of Yellowstone at Lone Cactus cottage in Pray, Montana. The distance was worth it, as the cottage provided a clean, cozy, well-equipped home-base. Dinner at Emigrant Outpost was unfussy and filling.
Day 5. For our second day at Yellowstone, we traveled through Mammoth Hot Springs to Lamar Valley. If you are looking for wildlife, take this route. We saw bison – lots and lots of them. And, we saw three bears while hiking on a trail and another one while in the car on the main loop. Our bear sightings on Slough Creek Trail were very unexpected because we were less than a quarter mile from the parking lot. In addition, the area is heavily wooded, so we didn’t see them until we were much closer than we would have liked. A great story… well only after some reflection from the safety of our vehicle. Do not take lightly the fact that Yellowstone is packed with wildlife – follow Park guidance, carry bear spray and be alert.
We stayed in Pray, again.
Day 6. Andrew and I worked remotely from the cottage all day, while the girls explored nearby and generally relaxed. I found that breaking-up the trip with this one work day helped me get back on track quicker when I returned. Consider doing this, if it’s an option for you.
The service was slow, but we otherwise enjoyed our upscale dinner and hand-crafted cocktails at the Fireside Room at Sage Lodge. Both the indoor and outdoor seating gazed towards a beautiful pond and valley dotted with small cottages and distant mountains.
Day 7. For our third day at Yellowstone, we traveled through Mammoth Hot Springs to Canyon Village. We spent a good portion of the day driving the main loop except for our hike on the trail to the overlook at Grand Canyon of the Yellowstone. Be ready for plenty of steps and narrow pathways on this trail.
One of the highlights of our trip was staying at Under Canvas in West Yellowstone. I chose a tent with a private bathroom and arranged for cots for the girls. It took a few tries to get our stove burning strong, but we soon were able to warmly glamp in the comfort of our king-sized bed. S’mores in the evening and to-go breakfast in the morning were included.
Day 8. For our last day at Yellowstone, we traveled through Old Faithful to Bay Bridge. We ate our takeaway breakfast from Under Canvas just inside the West entrance of the Park on the bank of the Madison River on Riverside Drive. The view was stunning. We visited Old Faithful and West Thumb – both of which were expectedly crowded.
We star-gazed from Under Canvas, again.
Day 9. West Yellowstone to Jackson, Wyoming via Yellowstone and Grant Teton National Park. Jackson is picturesque and walkable. It’s packed full of upscale amenities, photography shops and souvenir spots.
And, don’t let the kids miss shooting the laser rifle at targets around The Jackson Hole Toy Store.
We lingered over a bottle of wine and sushi at lunch at Suda Izakaya and sipped unique cocktails and Italian fare at dinner at Glorietta. We stayed at the perfectly-styled Anvil Hotel.
Day 10. We withstood a long line to grab a hearty breakfast at The Bunnery Bakery and Restaurant before heading towards Cody, Wyoming. We tacked on this stop in lieu of a more leisurely drive back home. That was definitely the right call! Do not miss the Cody Nite Rodeo, if you take a trip to Yellowstone. It’s outdoors and full of excitement. Bull riding, roping, barrel racing and bronc riding were the adventure I never knew I needed!
Day 11. Cody to Sioux Falls. Get comfortable, and head East towards home.
Day 12. Sioux Falls to Chicago. Watch the Sun set behind you, you’re almost home.
Our road trip was a hit for both the kids and the grown-ups. The relaxed comfort of driving our own vehicle paired well with our many fresh-air adventures. And, the scenery throughout the trip was mesmerizing and has kept us longing to return.
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