Road Trip from Northern Montana to Jackson Hole, Wyoming – Full Itinerary 

As much as I love exploring new cities, and being surrounded by the hussel and bussel, sometimes a mountainous getaway is just what the doctor ordered.  

I was not prepared for how magical and breathtaking my trip out west would be. As cliche as that sounds, this 10 day (mostly unplugged) road trip was the perfect way to calm down, forget life’s worries, and connect with nature. 

For me, planning and creating itineraries is PEACEFUL, however, I know that for some, that is the most daunting part of travel. I planned my days using my Stay Beautifully Balanced Planner. This is a planner I created for working women who strive to balance their lives both personally and professionally. Click HERE and use promo code MOUNTAINS for a discount to get your own SBB Planner.

We both checked our luggage, however this trip could totally have been done with a carry-on only! (I have a blog about my go to beauty supplies for traveling, you can find it here if you’re interested! All super carry on friendly. Hope it helps!)

If you love exploring new parts of the country, and aren’t afraid of venturing to the middle of nowhere, I highly suggest following my itinerary from Northern Montana to Jackson Hole, Wyoming. 

Beware this is a long one. I’m giving you the details of everything we did and everywhere we stayed. It’s super comprehensive!

Day 1:  We flew from our hometown, Roanoke, Va. to Kalispell, MT.

I flew with United Airlines. Always, remember to download the airline’s app a few days before hand so you can check in, and stay up to date with any changes or delays. (Oh, and to my surprise, there were no TVs on the flight. Download the Netflix app on your phone or laptop and download some shows so you can easily watch on board. They had some kind of “United Entertainment” app available for shows and movies, but I, nor several others around me, could figure it out or get it downloaded. I decided to stick with my tried and true: Netflix.)

Once we landed, we picked up our rental car at the airport. I used Alamo, and our total was $349.79 for the entire 10 days, totally worth it! They were very easy going (as was everyone in Montana/Wyoming). They even gave us a free upgrade to a Nissan Altima, which had awesome gas mileage and enough room for our luggage. If I remember correctly, we only filled up 4 times the entire trip and drove over 2,000 miles! (I drive an SUV, so to me, this was just AWESOME!)

The first thing we did upon arriving, was FIND FOOD! (Shocker, right?)

My friend recommended an awesome little restaurant, called Sykes.


Large portions, not so large prices. This place was quaint, cute, & has the BEST Huckleberry Bread Pudding. When we walked in, we didn’t know what a Huckleberry was, but after this, we ate it every opportunity we got! Huckleberries are similar to blueberries, and they only grow in the higher elevations of Montana and some in northern Wyoming. Montanans are VERY proud of them and you’ll see them everywhere you go.

After lunch, we headed to the town of Whitefish, MT.
We shopped, and explored for about an hour before heading to the St. Mary area. 

We checked in to our first cabin at Leaning Tree Campground. This cabin is located in Babb, Montana, which is only a few miles away from Canada.

You can book by clicking this link and searching “Leaning Tree Campground”:

When you sign up for Airbnb with this link, you will get $15 to use toward an experience worth $50 or more.

Leaning Tree Campground is located on the Blackfeet Indian Reservation, has a few different cabins, and is perfectly located to begin your trip to Glacier National Park.

You can find my complete review of Leaning Tree Campground here.

This is the cutest little place, very clean and welcoming.

NOTE: There is practically nothing for miles and miles on your way here. You need to make sure you have maps open before you start on your way, as you WILL lose service. Make sure your car is filled up with gas, there are limited to no gas stations . 

After we checked in, we drove around to find some dinner and get snacks from a market near by. Here is where we went wrong. We ate at a place called “Two Sisters”. It was severely overpriced, had a pretty odd vibe inside, and honestly wasn’t that yummy. (There was a cute dog outside, and that was the highlight.) When we got back to the campground, we discovered that Leaning Tree HAS A CAFE, that smelled awesome and the food looked amazing. I regret not eating here. 

At the market, we picked up a styrofoam cooler, ice, and some snacks. HOLY COW Y’ALL! Do this BEFORE leaving Kalispell. Once you arrive in Babb, there are so few options for food/convenience stores, that the prices were CRAZY! (Like, $6 for a box of crackers, and $4-5 bottled drinks.) 

Later this evening, we drove around looking for “critters” as Josh calls them. (Animals.) We saw elk and a mountain lion! Awesome way to start our journey!

Day 2: Glacier National Park- Going to the Sun Road

We woke up, ready to roll! 

We checked out early, and drove the 10 minutes to St. Mary Visitor Center. 

We purchased the YEARLY pass for National Parks. You can buy that here, or just when you arrive.   If you’re going to multiple parks in multiple states on this trip, this will save you money. (Plus, it’s good for a year, so that’s a great excuse to plan another trip!)

At Glacier National Park, the best thing to do is to venture on to the “Going to the Sun Road.” Depending on the time of year, make sure you check the road closings so you don’t get stuck or waste time. 

You have 2 options here. You can 1. Take the free shuttle, or 2. Drive yourself. While the free shuttle seems awesome in theory, DRIVE YOURSELF. There are going to be so many awesome photo opportunities, wildlife sightings, and trails you want to do along the way, and you are going to want to be in control of your own stops!

We did this trip in September, and Glacier was not crowded at all. It was perfect actually! Not too cold, no lines, no traffic! 


Glacier Recommendations:
St. Mary and Virginia Falls hike- Near East Entrance. 3.6 miles round trip
At Logan Pass- Highline Trail hike Or Hidden Lake Trail (Hidden Lake trail is about 3 miles out and back, and only about 500 ft. elevation, so pretty easy to do!) 

You can do The Going to the Sun road in just a few short hours, but you can also make it take as long as you want, depending on how often you stop to hike trails or take pictures! 

It only takes about an hour and a half from one side to the other if you drive straight through! 

The beautiful road ends at Apgar Visitor Center. From here, we drove for about an hour to our next location on Flathead Lake. 

Let me start by saying this… I booked this reservation on Airbnb on a whim, and mostly because it was conveniently located for my next day. This was by far the COOLEST Bed & Breakfast I have ever seen. 



You can find my complete review here. 

If you are following this itinerary, or traveling to Montana AT ALL EVER, I highly recommend staying at the Fort Rollins Bed & Breakfast



We stayed in “The Orchard Cabin” and it was so lovely, I can barely put it into words. The owners, Jason and Andrea, and are so welcoming, gave us a tour, told us their story and the history of the property, and made us a KICK BUTT breakfast the next morning. We loved this place so much, we bought our friends a gift card to visit before we left! 

You can book by clicking this link and searching “Fort Rollins Bed and Breakfast.”

When you sign up for Airbnb with this link, you will get $15 to use toward an experience worth $50 or more.

(Also, there is a zip line, free kayak/SUP rentals, and the views are amazing! I’d recommend staying here as a couples retreat, or family vacation!) 

For dinner this night, we ate at The Tamarak Brewing Company. (Disclaimer, we ordered to go so we could come back and eat it at the B&B.) The food was awesome, the beer was awesome. Enough said. 

Day 3 & 4: Missoula to visit friends

We woke up pretty early in our beautiful Bed & Breakfast, ate the most delicious breakfast Jason made us. (It was the best french toast I’ve ever had, and he makes his own bread.) 

We drove to Missoula to meet up with my lifelong best friend, Hannah.

Her and her husband let us stay with them for two nights, and obviously you can’t do that! 😉
So I found some places that look affordable and cute for you!

You can check them out here!

Campus Inn

Stonecreek Lodge


We arrived on a Saturday, and Hannah took us to explore some of the local markets. These markets were AMAZING! So many local vendors, we tried fresh produce, cheeses, oils, gawked at beautiful flower arrangements, art, and locally made jewelry. 

Recommendation: Get a sandwich at Ninja Mikes. They were a vendor at the market, but also have a store. Either way, you don’t want to leave the area without making this happen. Ninja Mikes serves up local ingredients on their sandwiches, and tell you where each component comes from. Not to mention, it’s the best breakfast sandwich I’ve ever had. 



(Yes, you probably noticed that we ate two breakfasts this day. No shame. Don’t judge us.) 

After the markets, explored the shops in town, and then we went to the National Bison Range.
Address: 58355 Bison Range Rd, Charlo, MT 59824



This is a fun place with a lot of little trails, awesome views, and a great opportunity to see elk, bear, and of course,  buffalo! 

On Day 4 in Missoula, we ate breakfast at Wheat Montana. You have to go here! They have cinnamon buns the size of your head! We got a huckleberry cream cheese cinnamon bun, and loved it so much we got it again the next day! 

We drove up to Rock Creek (a river near Missoula) with one mission, and that was to see big horn sheep!


Day 5: Road Trip to the Northeast Entrance of Yellowstone

From Missoula, to the Northeast Entrance of YNP, is about 5.5 hours, but if you do it right, it goes by fast and is insanely fun. 

We stopped in Helena, Butte, & Bozeman along the way! Butte was by far the BEST! 

Helena: We hiked up to a water tower. Honestly, you can skip this. Not super cool. 

Butte: Spend more time here! It’s beautiful, and has a lot of unique things to do. If you do anything, you have to eat at “The Freeway” and order the “Wop Chop.” 

Address: 2001 S Montana St, Butte, MT 59701

We visited the Copper King Mansion here. We didn’t have time for a tour, but I wish we did! 


Then, we took a picture of the oldest brothel in America. Depending on the time of year, you can do a tour here too! It’s supposed to be “haunted” if being scared is your thing!

After that, we visited “Berkeley Pit”. 

 It’s $3.00/person to enter and you get to see this toxic quarry (think pond) that if any animal or bird lands in it, they will die. Don’t judge us, it’s interesting. (They have sirens that go off frequently to keep birds and animals away!) 

Here are some things that we didn’t plan for, but wish we did:

Ringing Rocks Google a video of this, super cool! When you hit the rocks with a hammer, they ring like bells!
Grasshopper Glacier A hike to a glacier with grasshoppers frozen inside.
Elk Collection Note: You can’t just stop by here, you have to email Jim at 2jd3law4@gmail.com and set up a time!

Finally, we made it! To get to the NE Entrance, you go through the North Entrance.

I recommend seeing Mammoth Springs here when you enter, because you’re already there!

Then on your way to the NE Entrance, you pass through Lamar Valley. If you’re interested in seeing wildlife on your trip, prioritize this. We saw elk, moose, bear, wolf, bison, and mule deer.

Tip: BRING YOUR BINOCULARS. We had cameras with us, and binoculars, but regret not renting a spotting scope. There are stores outside of the parks that rent them and I highly recommend this! 

Photo Credit: Josh Long, IG: @jlongfishing)

If you’re a newbie to wildlife searching, no worries. There will be cars pulled over and people looking through scopes whenever they see something! Everyone is super nice, so if you can’t see it, just ask to peek through! Your best bets for seeing wildlife are going to be at dusk or dawn, so plan accordingly. However, it’s almost guaranteed that you’ll see SOMETHING here no matter what time of day it is.


We saw our “Critters” and then headed out of the park to our hotel. This night, we stayed at The Alpine Motel of Cooke City.

You can book here

If you know me at all, you know I LOVE cheesy Hallmark Christmas movies. The town of Cooke City, felt just like that!

When Josh and I arrived, we instantly fell in love. (& he’s not a Hallmark fan. He loved the town, but I was a total fangirl.)

The weather was perfect, it felt like Christmas, we held hands and walked to dinner and honestly it was just magical. This town is TINY, but I highly recommend it! Everyone we talked to felt like family! We ate ate the Beartooth Cafe, which again, was amazing! So homey, so Hallmark, they should make a movie there! 

Hallmark worthy, right?


Day 6: Yellowstone National Park

Okay, maybe we did this wrong, but it worked for us! We busted through Yellowstone in one day. (Don’t worry, I can hear the “boo-ing” now through my computer.) We did technically do Lamar Valley and Mammoth Springs the day before, and we gave ourselves time to go back the next day if we wanted, but we saw everything on our list and didn’t feel rushed! If you wanted to spend more time exploring, “critter-searching”, or hiking, you would absolutely want to break this up into a few days! 

Moose in Yellowstone. Photo Credit: Josh Long, IG: @jlongfishing
Lamar Valley in YNP. Photo Credit: Josh Long, IG: @jlongfishing

You can read my itinerary blog on YNP here.

Here is a map for your convenience. 

We exited YNP through the West Entrance, and stayed at a cabin in Idaho. Super cute place, though we weren’t here for a long time, we arrived late, and left early.

The Preserve on VRBO
You can book here.

Day 7: Idaho and Grand Tetons 


On day 7, we woke up, and made our way to Grand Teton National Park! This was about a 2.5 hour BEAUTIFUL drive! 

We checked off the 4 main things to see in the Grand Tetons! You can read my blog about that here!

Day 7 was our “Splurge” night! We stayed in a HUGE CABIN with a super cool swimming pool, splurged on dinner, ordered room service dessert, and spent too much money! (Sometimes, you just gotta treat yourself, right?) 


Snake River Lodge & Spa
You can book here: https://www.booking.com/hotel/us/snake-river-lodge-spa.en.html?aid=1858330&no_rooms=1&group_adults=1 

Day 8 & 9: More Grand Tetons and Jackson Hole Exploring 

The last two days for us, were super low key! We spent a ton of time shopping and driving along the Moose Wilson Road searching for animals! We love photography, so we also spent a lot of time capturing beautiful shots of the mountains and wildlife! You can check out Josh’s photos here: INSTAGRAM JOSH LONG @jlongfishing https://instagram.com/jlongfishing?igshid=13vp50hkayyce 

View my list of things to do in the Jackson Hole here! 

Both of these nights we stayed in “The Inn at Jackson Hole.” The best way to describe this place is a trendy, modern, lodge-ish, motel!? 




The Inn at Jackson Hole 

You can book here.

Day 10: Going Home 

On Day 10, we boarded our flight and headed back to Roanoke!

Have you been to any of these places? Did I miss anything? Feel free to comment below.

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