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Fall Roadtripping in Montana and Wyoming

Taking in the views from Grey Cliffs Ranch on a fall roadtripping itinerary in Montana and Wyoming.

Looking forward to taking in this view at Grey Cliffs Ranch, part of our fall roadtripping itinerary.

Are you a fan of fall roadtripping? Alan and I like nothing better than exploring when the leaves are turning and the air has that crispy feel of fall. But what if it rains or snows? I guess you know where this boomer road trip story is going.

Driving the Beartooth Highway in Wyoming and Montana has been high on my to do list for a long time. And this month, Alan and I were finally going to make this fall roadtripping adventure happen. And it still might, along with exploring Yellowstone National Park’s Lamar Valley. Alan calls it “Donna’s trip.”

But the Beartooth Highway has been closed due to snow 4 times in the last 2 weeks so things aren’t looking real good. And there wasn’t a single room to be found at Mammoth Hot Springs (closest in-the-park-lodging to Lamar Valley). But we’re flexible boomer travelers, right? We’ve adjusted our itinerary, within the confines of rooms that have already been bought and paid for, which is the only way to be sure of lodging at the end of a busy September season.

And so our fall roadtripping itinerary for Wyoming and Montana looks like this:

We’ll be driving to a little beyond Red Lodge, Montana, for a one-night stay at Inn on the Beartooth. And if the road that keeps calling my name is open, Alan and I will spend the next day driving as much of the Beartooth Highway as we can.

Then we’re turning east in an attempt to beat the bad weather for a three-night-stay at Wyoming High Country Lodge in the Big Horn Mountains. We plan to explore the Big Horn Canyon National Recreation Area. And, if the weather cooperates, Alan will be checking a to-do off his list as we drive the Pryor Mountains on the Montana/Wyoming border in search of the wild mustang herd.

This road trip ends with three nights at one of our favorites—the luxurious Grey Cliffs Ranch in Madison Valley, Montana. If Alan and I can tear ourselves away from Grey Cliffs’ beautiful scenery, we’ll be exploring Lewis and Clark Caverns State Park before it closes on Oct. 1, or maybe we’ll explore one of the area ghost towns.

If the weather cooperates, I’ll be reporting back on the hiking trails, scenic drives, local restaurants and lodging that Alan and I experience on this trip. And if it rains and snows? Alan and I will return with plenty of new articles and edited photos when our fall roadtripping turns into a creative retreat.

Want to keep up with us in “almost” real time? If the Internet and cell phone service work (and they might not in remote locations), I’ll be posting photos and updates on Instagram, Twitter and at the My Itchy Travel Feet page on Facebook. Don’t forget to follow us!

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