An I-90 Roadtrip

Hi all - I'm planning a solo road trip from Chicago out to Walla Walla in early August, and would love some info about what to see and where to drink. My general trajectory puts me on I-90 from Chicago through Spokane before I turn south to Walla Walla. I'll be traveling through southern Minnesota, South Dakota, and Montana. 

I've never really spent any time in these states, so I thought I'd turn to the group I trust the most that enjoys wine, food, and traveling. Any suggestions about eating and drinking, hiking, fishing, or cannot-miss restaurants/towns/vistas on the trip, I'd love to hear it. And if you happen to be on the route west, I'd love to share a bottle or two. 

Thanks all! 


  • Jerome. Hit up Bozeman. Feast and Plonk are great places to eat. In Missoula, check out Plonk, Rumours, Red Bird Wine Bar, Missoula Wine Merchant. I'd recommend taking 93 south from Missoula for about 15 miles to Lolo. Than take I-12 West. This takes you over the Nez Perce Indian reservation and right to Walla Walla. It's only an hour or two longer driving time but totally worth it. Plenty of great breweries in Montana also.
    Have fun.
  • In reply to Timothy "Jeremy" White:

    This is exactly what I was hoping for. Thanks so much!
  • It may not make sense to stop in Madison on your drive, because it is so early into your trip - but you should definitely check out the food and beverage scene there. There are a handful of restaurants that are killing it - L'Etoile especially.
  • In reply to Aaron Rostad:

    Awesome - I can probably make that happen. Thanks!
  • In reply to Jerome Noel:

    Mt. Rushmore is pretty cool. But just be prepared that the Dakota's portion of that is pretty bleak.

    Stop at Wall Drug just to break it up. Make sure you're well-rested for that because it's basically 450 miles of nothing.

    The interesting nature portions are all in the Idaho/Montana portion of things. Possibly my favorite highway sign ever is in Idaho. The exit for Anaconda/Opportunity. Don't think you'll see it though unless you're passing through Spokane and then heading south to Walla Walla.
  • If you have any extra time to spare, Yellowstone is spectacular. Truly one of the most beautiful places I have ever been to.
  • In reply to Morgan Harris:

    I might not be able to see it on the way out - it sounds like the route through Lolo recommended above sounds cool. But there's always the return trip...
  • Hi, Jerome.

    Will you be carrying a fly rod? A lot of great water between Billings and Spokane. Do you have anyone on the ground in Walla Walla to taste with? Would be great to meet up to wet a line or show you around my winery in Walla Walla.
    Send me a message if you would like to connect:

    Don't miss Passatempo Taverna and Gramercy Cellars in Walla Walla.

  • In reply to Timothy "Jeremy" White:

    Blackbird in Bozeman is great also!!
  • In reply to Kristopher James:

    Great wines from Reininger and Gramercy. I need to hope over to Walla Walla for a weekend.
  • Most of my extended family is in South Dakota, so I have spent many summer weeks there! I cannot say that I've had any spectacular restaurant or wine experiences, but in Rapid City, there are lots of solid breweries and pubs (Firehouse Brewing Company and Independent Ale House, for example). There's also a cute Aussie-owned coffee shop with good food called Essence Coffee Roasters that I visited earlier this summer. For delicious ice cream, go to Armadillo's.

    The Black Hills are truly beautiful, and that's what I'd say is most worth a visit in the state. I have to disagree with Morgan there—it's an amazing natural environment! Head to Custer State Park or Wind Cave National Park for a beautiful drive or hike featuring plenty of wildlife and amazing vistas. The Mickelson Trail is gorgeous and great for a bike ride or hike of any length, and a drive through the Needles Highway is pretty spectacular. You don't need to actually drive in, but if you're in the area, get close enough to Crazy Horse to take a look—fascinating to see something like this just partially completed. Relatedly, you can see Mount Rushmore from a pretty wide surrounding radius, though the hike that goes up close to the faces is worthwhile as well. Wall Drug is entertaining but touristy, not a must-see in my book.

    Sounds like a great adventure! There are some bleak passages in the middle of the country, but just stock up on podcasts and you will be fine. Enjoy!
  • Sturgis is Aug 3-12. Take some time and get weird. :)
  • Jerome. There is a large fire on highway 12 right. There is talk of closing highway 12 heading to Idaho. So you might have to go through Spokane.
  • In reply to Timothy "Jeremy" White:

    Thanks for the head's up! I won't be there for another 10 days or so, but I'll keep it top of mind and check on the updates as I get closer. Thanks again!
  • In reply to Aaron Rostad:

    L'Etoile is awesome. The few plates I had at the bar were delicious, and Stephen is crushing the wine list, with tremendous value to be found. Especially the VEP Green Chartreuse for $25...