Just be aware if you take the Beartooth Pass, it isn’t for anyone afraid of heights. And there can be snow.
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We did a similar trip in the opposite direction four years ago. Since I also wanted to check North Dakota off my map (I’m up to 46 states now 
) we did this route:
coming from Badlands and Custer State Park (best Bison sightings!) through Spearfish Canyon and Deadwood north on 85 to Belfield, ND/Theodore Roosevelt NP. I found 85 between Belle Fourche, SD and Bowman, ND absolutely stunning in its nothingness and remoteness. We then turned west via Medora and joined I 94 in MT towards Yellowstone. We took the Beartooth Hwy and entered Yellowstone through the Lamar Valley. I agree with previous posters that it was the best place for wildlife watching/sighting for us
I would do this trip again in heartbeat. You are in for treat.
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Everything said above about the Tetons, Yellowstone, Wind Cave, Custer State Park, Roosevelt N.P., … yes.
Fort Mandan in North Dakota was a really enjoyable short stop for us passing through N.D. - Not a huge time investment, close to the road if you go the northern route, and well worth a stop if you’ve got any interest in history (Lewis and Clark winter encampment).
if you’ve got any interest in American Indian history, there are some really important spots on either tour route. The Pine Ridge Reservation abridges the Badlands, and they have an innovative shared management program for part of the national park. You can get tours through businesses in the reservation that would show you the Badlands, but also a bit about the reservation (Wounded Knee?).
Pipestone national monument in SW Minnesota is interesting, and there used to be an outdoor drama near there that was WAY cheesy, based on Longfellow’s poem about Hiawatha (which apparently was set there). Sioux Falls, SD is based on an actual waterfall in town that is pretty surprising and fun.
Oh, and the interstates through the Dakotas FLY. (faster than I could easily go in my loaded down Prius with roof-rack)
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The one year that both my kids were in high school together they both went on church youth group mission trip to Pine Ridge Reservation. I think they learned a lot that week. Years later it was cool when one of the Colorado University graduation honorees was from Pine Ridge.
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Thanks everyone.
Based on all the feedback so far, I think this is our approximate route, from left to right. This doesn’t take into account all the stops and travel within the regions of the stops, particularly around Yellowstone or traveling through the Black Hills, etc., but it shows the approximate route between major locations.
Any thoughts are appreciated. Booking flights soon. This trip would be late latter half of September, perhaps into very early October.
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Is there a reason to go to Bozeman rather than taking the Beartooth Highway direct to Billings?
Mostly to see Bozeman (and the Museum of the Rockies, etc.). But not a must-do if the consensus is that the Beartooth Highway to Billings is more interesting.
The alternative – fly into Bozeman and then return via Beartooth and Billings, looks like this, at least on Google Maps. Not a huge fan of doubling back and going through Yellowstone to get to Gran Teton but not a big deal.
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Not much to add to all the great suggestions, but we stayed in a suite in the Yellowstone Lake Hotel which was wonderful. Food was expensive and just ok. Some lodging in Yellowstone is closed in Oct.
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I mentioned this earlier. Watch for snow in the Beartooth Pass and elsewhere. It comes early and can cause road closures. It just reopened as of June 5th this year. Wonderful views but you must know the mountain weather conditions.
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I’ll second this. And since the OP just said the trip is late September or maybe October, I’ll also add that you could get snow in places you wouldn’t expect. I remember having snow in Yellowstone itself in late August when we went one year.
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Hi. Resurrecting this post. I’m about 2/3rds of the way done with planning and booking hotels (flights done). I have about 3 days (2 non-travel days and 2 partial travel days in/out of the area; 3 nights total) that we can spend in the broader Black Hills area including covering Devils’ Tower, Mount Rushmore and anything else to do around there (I could also shorten it by one day if that is overkill). We will be coming from Medora/Theodore Roosevelt National Park on the first day and departing East in the direction of Sioux City on the day out. This will be during the last week of September.
Looking for suggestions on where to stay and to a lesser extent other things to consider doing in the Black Hills area besides DT and MR. It would be easier to stay one place for 3 (or 2) nights, but also possible to split the stay in two places if that is better.
Thoughts?
Thanks.
I also just realized, by coincidence, that we are going to be in the area on the exact days of the annual Buffalo Round Up at the Custer State Park…
Not sure if that’s good or bad. Sounds interesting but we were generally looking forward to missing the crowds during this trip and I assume this will draw them to the area. Our flights are set, so it is what it is…
Wind Cave (and perhaps Jewel Cave though that might be overkill).
And you probably want to see the Crazy Horse memorial.
I assume you are going to Badlands on the way out? Also maybe worth seeing the Minuteman Missile Site which is close by?
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Custer State Park is beautiful and certainly worth a visit, although I’m not sure how the Buffalo Roundup will affect how crowded it is there. When we visited the area in 2018, we stayed in Keystone at the Backroads Inn and Cabins, which we really enjoyed.
When we stayed in the area a few years ago, we used Hill City as a base, and that worked out really well. Nice walkable downtown area, some tourists but quieter than Keystone. Another vote for Custer State Park, well worth seeing.
We stayed at Shady Rest Motel in Custer It’s individual cabins of varying sizes. Very clean and nice. Good central location.
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Looking into this more, I think we can reposition from Medora, visit Devil’s Tower and hike around it then continue on to some place closer to Custer all in one day. Then use that as a base camp for Rushmore, Custer, and maybe even the Badlands (though we were thinking of doing those on the day we are heading east anyway).
We arrive in the area the day before the morning of the buffalo round up. And it doesn’t seem like there’s a lot to do at Devil’s Tower other than see it, and the main hikes are only 1-2 mile around it. Seems like we could get there is about 3.5 hours according to Google, end up there early afternoon to see and hike (and do lunch somewhere), then have time to do about 2-2.5 hours to get to wherever we stay closer to Custer.
If we do this, we end up near Custer in time to go to the buffalo round up the next morning and then still have a couple days to further explore Custer, go to Rushmore, explore Deadwood, etc. Then hit Badlands on our departure day and keep heading east.
Thoughts on this?
Years ago we camped at Custer KOA, which also cabins (with linens). Close-ish to many sights
At the time, they ran school buses in the evening to Mt Rushmore and to Crazy Horse. That was ever so handy! And nice to go when cooler. I don’t see evidence of a bus option anymore.
We stayed at the Comfort Inn in Hill City. They had rooms with lots of beds, which works for us. haha. But it was nice and we enjoyed it. Good location
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