A Weekend on a Montana Ranch: Experiencing Big Sky Country Firsthand

I won’t lie- domestic destinations have never held as much allure to me as international ones. I’ve always saved my dollars for overseas trips- in fact, I’ve visited twice as many countries as I have states! (That would be 38 and 19, for your information. The shame, I know.)

But there’s something about Montana that has always intrigued me. Maybe it’s because I love horseback riding, or because I like Westerns, or because I not-so-secretly dream of living in the country someday. Regardless, when my friend McCall (the friend I went to India with!) invited me to her Montana ranch for Labor Day weekend, I booked a ticket immediately.

Well, it turns out there’s a reason they call Montana Big Sky Country, and there’s also a reason why celebrities are buying up all the land. Montana is gorgeous.


After some obligatory cowboy boot shots at the ranch, we headed to town.


Livingston is as cute of a Wild West town as you can imagine, though it’s a little more yuppie than cowboy with both a yoga studio and sushi restaurant. And thank God- I would never be able to do country life without sushi in a thirty-mile radius.



I came close to buying a cowboy hat but opted out last minute. Because when will I ever wear a cowboy hat again?

Plus, I would’ve had to buy a men’s hat because fun fact- I have a huge head. (I’d like to think this is because of my hair. Or my brain. Or both.)


On the way back home we passed a golden field filled with grazing black cows. Naturally, Eleanor and I hopped out to snag some new profile pictures.



Once we got home we tried to coax Lulu, the shy Bernese mountain dog who melted my heart, out of the car. No cigar, but look at that face!


And then (and this makes me a terrible travel blogger as I didn’t take a single photo), we had a huge barn party with kegs of Blue Moon and local ales, a live country band and even some celebrity guests. (Well, sort of, but I was told Aaron Eckhart’s parents stopped by.)

The next morning we woke up (a bit groggily, I admit) to this view from the kitchen.


For breakfast we had homeground whole wheat pancakes with homemade chokecherry syrup. They were so good we didn’t even bother to pass out plates, and ate them standing in our pajamas.


We then headed outside to play with more dogs. I was kind of obsessed with Pepper, the English setter. Isn’t he handsome?


Cowboy, the aptly named Leonberger, was pretty dapper as well.Montana_Ranch_Leonberger

And in effort to burn off those pancakes we then went for a mild hike in the woods. As in like 15 minutes. That probably burned off like a teaspoon of chokecherry syrup. Right? No? Montana2

After our “hike”, we spent the rest of the afternoon riding four-wheelers through the property and soaking up views like this:Montana_Ranch_Clouds






Once we had our fill of big sky views, we high-tailed it back to the cabin for beers and the best peach cobbler I’ve ever tasted.


We capped off the weekend by swinging by a local country bar for dirt-cheap beer and dancing. And for my last night in Montana, Big Sky Country went all out with these cotton candy clouds.


Well thanks Montana, for contributing to my country life fantasies and just for being so goddamn gorgeous. And thanks of course to McCall and her lovely family for having me!

Have you ever visited Montana? Would you want to?

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About Ashley Fleckenstein

Ashley is a travel and lifestyle blogger who lives in Ann Arbor, Michigan. Since college she has au paired in Paris, backpacked the world solo, and lived in Uganda. Her work has been featured by Buzzfeed, Forbes, TripAdvisor, and Glamour Magazine.

40 thoughts on “A Weekend on a Montana Ranch: Experiencing Big Sky Country Firsthand”

  1. Fantastic! I have never been, but from boots to dogs (I am a hovering “Helicopter Dog Mom” to 3 canines, having had 5 before) this was so very fun! It looks beautiful! AND, when in San Antonio, I had to buy a men’s Stetson, (due to the female hats not fitting), and so this posting made me smile! Let’s hear it for women with big hair and huge brains! Great post! Cheers! – Leah

  2. I underestimated Montana and also Wyoming until I moved to Jackson, WY in college. Undeniably beautiful, and full of western “culture”. While I love the summer and fall, I don’t know if I would be able to take either states bitter cold winters.

  3. Looks like such a nice weekend! I’ve been to Montana before on a family road trip and it is beautiful. I bought a cowboy hat on that trip and I have maybe worn it twice since! So good choice, haha!

  4. Looks great! I wish I could see more of the US. When I was doing travel nursing that was my plan (but moving here changed all that) & I sort of wish I had a couple years to travel in the US before this move. MOntana looks great. I saw a little of it on the real housewives of NY lol

  5. That looks absolutely amazing and sound like you had a great trip. I too feel like i’m more drawn to international travel and sometimes forget that places like that are right here! I will definitely have to take a trip over there before I leave.

  6. I’m bad with domestic travel as well. The appeal never seems as good as other countries but I’m always happy when I do go somewhere close by.

    The town looks like classic mid-west. Killer landscape and love all the dogs.

  7. I feel like the American West is the U.S.’s unsung hero when it comes to tourism. Unbelievably beautiful, with so many natural wonders, parks, and wilderness areas protected for posterity–yet the big cities like NYC, Chicago, SF, etc. are (understandably) focused on when non-Americans come to visit, I’m always like “You HAVE to go to the Rockies” or what have you.

    Love the gorgeous photos you took in the Big Sky Country!

  8. Montana is my FAVORITE place on the planet! I lived in Bozeman for a summer and it was amazing. There is a great Mexican place and an antique shop in Livingston. I got the coolest cowhide coasters there! The best place I ever had sushi was a place called Louie’s Down Under in Bozeman. My friend use to work at a resturant near Yellowstone and met Katy Perry and John Mayer there. Your right, a lot of famous people have homes in Montana. Who would have thought?!

  9. It looks stunning there. I have never ventured to Montana or many other states in the US. It’s not until you get away that you realize how much there is to see in your own backyard! I too have a very large head. My dad has always said big head, big brain!

  10. Oh my gosshhhhhh this looks so amazing! The more I travel abroad the more I find myself wanting to actually do a US roadtrip because, let’s be honest, our country is pretty fricking beautiful. And I want an excuse to dig my cowboy boots out of the closet, sigh… Your photos are gorgeous!

    • A US road trip would be so much fun. I did one years ago with my grandparents to the south but I’d like to do the classic Route 66 one someday! And thanks so much- I didn’t have my usual camera and had to borrow my dad’s G12 so it was a bit harder shooting :)

  11. Ok, I’ve never visited Montana and never wanted to either. But now I’ve seen these photos and find myself daydreaming of big sky country! I’ve always known that the U.S. has a ton of great areas well worth exploring, but this was never on my radar before. So thanks for adding that to the list, I guess! ;)

    • Glad to hear it! I definitely want to go back to see Yellowstone as well as Cowgirl up, which is a camp where you and other women ride horses and drink wine for a week. Sounds pretty great to me! :)

  12. Oh man, I love Montana. I went for a work trip once and I was so pleasantly surprised by the beauty and tranquility! If it wasn’t so crazy cold for a huge part of the year, I would consider moving there!

  13. I’m in the same boat as you, having traveled internationally more than domestically at this point. I would definitely like to go Montana though! I grew up on the East Coast and I have loved exploring the west but haven’t been to Montana yet. These pictures are quite enticing!

  14. Holy COW! Gooorgeous. I’ve been wanting to go out west for some time now, but this has cemented it. I NEED TO GO OUT WEST.
    ps. Just found you via Paper Planes – can’t wait to read more!

  15. I have really started to appreciate exploring my own backyard (if I can consider THE ENTIRE US my own backyard, that is). The past year had a lot more domestic travel for me than usual and I have even more on the docket coming up. I spent a bit of time in Montana in high school and would love to go back now. Gorgeous!

  16. Nice Blog Ashley,
    Thanks for sharing your pictures. Iv been to Montana twice to visit family in White fish and in Livingston.
    If any of your followers choose to go to Livingston…Be sure to take in the view of the “sleeping Giant” Mountain.

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