A family adventure: Rafting, horseback riding and hotel hopping 1,000 miles from Jackson Hole to Glacier

Jul 19, 2021

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Two grandparents, one parent, two kids, nine days, 1,098 miles, three states, two national parks, countless hiking trails and five different places to stay. What could possibly go wrong?

As it turns out, luckily, not much went wrong as three generations of my family set out for a big summer adventure across Wyoming, Idaho and Montana.

We explored Grand Teton National Park, spent multiple days in Glacier National Park, went “glamping” in a tree-top tent, rented a Montana house with insane porch views, rode horses in Wyoming, floated a river in West Glacier, stayed at a brand-new Marriott-affiliated hotel in Jackson and hiked until our legs couldn’t take it anymore. And we mostly didn’t go broke or crazy along the way.

In case this sounds like your ideal sort of family vacation, here’s what we did and how we did it.

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Open-jaw flights, one-way rental car

After delaying, changing, canceling and replanning this trip for more than a year due to the pandemic, we wanted to enjoy both Wyoming and Montana on this one trip.

But with kids, we hardly wanted to make that eight-hour drive between Grand Tetons and Glacier National Park a round-trip adventure we had to do twice if we didn’t have to.

So, we decided to fly into Jackson, Wyoming (JAC) and home back to Texas from Glacier International Airport (FCA). That’s known as an open-jaw ticket where you fly into one airport and home from another. This also meant locking in a one-way car rental that we picked up in Jackson and turned in at the Glacier airport.

(Photo by Summer Hull/The Points Guy)

Thank goodness we locked this in before the great car rental apocalypse really hit or we probably wouldn’t have been able to book anything at all since rentals are extremely scarce in Montana and Wyoming.

We used up flight credit we had leftover from canceled 2020 trips to book the flights, but depending on your origin, airline miles can be a great way to book this sort of trip. In particular, LifeMiles would have been great at just 7,500 miles each way from Texas to Montana on United-operated flights when available.

The one-way SUV rental was a bit of a budget-busting bummer as since it was booked as a one-way rental, Hertz charged an additional per-mile fee of 25 cents per mile.

However, even with the over 1,000 miles we drove, that $250 additional in mileage fees was still better than trekking all the way back to Wyoming and incurring another overnight hotel stay just to turn the car into the same spot where we rented from.

(Photo by Summer Hull/The Points Guy)

Sometimes the best way to cover more ground on a trip is to not backtrack to where you started. It can cost more in some ways, but is worth considering and pricing out as an option.

Where we stayed

Just as we did when we explored three islands in Hawaii with this same three-generations crew two summers ago, we didn’t stay in the same spot for very long. This means packing up and moving our lodging relatively frequently. On this nine-day/eight-night trip, we stayed in five different places.

That won’t work for everyone, but how much ground we cover on these trips, it’s perfect to avoid backtracking or wasting too much time in transit.

New Cloudveil in Jackson, Wyoming

Our first two nights were spent in luxury at the brand-new Cloudveil property in Jackson’s historic town square. This is an Autograph Collection property where you can earn and redeem Marriott Bonvoy points.

(Photo by Summer Hull/The Points Guy)

My two-night stay was provided by the hotel in order for me to give a “first look” to TPG readers, but I used 50,000 Marriott points per night to book the stay for my parents in their own room. Cash rates there for the rest of the summer are extremely high and some nights are sold out entirely, but it can be a solid value on points.

(Photo by Summer Hull/The Points Guy)

There are also parking and destination fees to be factored into this stay, but overall it was a great way to start the trip and put my Marriott Platinum perks to use for free breakfasts each morning.

Related: These are the best Marriott credit card offers right now

Fairfield Inn & Suites in Butte, Montana

After about five hours of driving to head from Wyoming to Montana (and experience Virginia City along the way), we spent the night at the Fairfield Inn & Suites in Butte, Montana. Butte wouldn’t be my recommendation for a final destination in Montana, but it was more than fine for an affordable overnight.

The hotel cost us about $110 per night and came with free breakfast served by the friendliest staff I had encountered in a long time.

If you had wanted to use points, it is a Category 4 Marriott that is pricing at 20,000 Marriott points per night for most available nights this summer.

Home rental outside West Glacier

While we lean into sleeping near where we are exploring, once we got to this part of the trip, it made sense to have a home base for a few nights. This way we could have a headquarters for the bulk of our Glacier National Park adventures, wash clothes and cook dinners.

(Photo by Summer Hull/The Points Guy)

We rented a pretty spectacular home in Colombia Falls about 20 minutes from the West Glacier entrance to the park.

This home sleeps up to 15 and runs anywhere from $600 to $1,500 per night, depending on your dates. Our early-June nights were about $800 per night, which was a lot, but really not a bad deal given the pricing for lodging that close to the park since this meant we didn’t need to book multiple hotel rooms and could cook our own meals.

You can use points to offset the cost of some home rentals in order to keep cash in your wallet.

Under Canvas glamping

After three nights of home living, we slept closer to the stars in a canvas tent just outside the West Glacier entrance at the Under Canvas Glacier location.

I’d been wanting to try out Under Canvas for a number of years, so this seemed like a good opportunity.

(Photo by Summer Hull/The Points Guy)

We had a lot of fun in our tents for the night, but renting two of the larger tents actually cost more money cumulatively than the home rental on a per-night basis. So this is just something you do this for the experience, not to save any money. Real tent camping in the park may save you cash, but the glamping approach is an experience — not a money-saver.

TownePlace Suites in Whitefish, Montana

The last night of our trip was spent about 15 – 20 minutes from the Glacier International Airport in Whitefish, Montana, at the TownePlace Suites. This is also a Category 4 property, making it an affordable place to stay if you have points to burn.

We spent 25,000 Marriott points for each room. If you wanted to use points to stay here and drive into West Glacier each day, it’s doable, but factor in about 35 – 40 minutes each way.

What we did

Walking and shopping in Jackson, Wyoming

Jackson is a walkable, fun, lively town that is worth at least an afternoon if you are ever in the area. There are many solid food options, but if you are going at a peak time, (like the entire summer) you may need to make a dining reservation in advance as things were very full.

Even if you want take-out, you may need to plan ahead unless pizza sounds good since some restaurants stop taking to-go orders once their dinner rush hits. While there are plenty more great spots to pick from in Jackson, we’ve personally enjoyed Local, Moo’s Ice Cream and Persephone Bakery.

The Bistro at the new Cloudveil was pretty solid, too.

While you are browsing the town square, don’t miss the shop Made, which is always fun with an eclectic mix of local handmade goods. The kids also quite enjoyed the rows and rows of goodies available at Teton Toys.

Horseback riding

Did you really go to Wyoming if you didn’t play the role of a cowboy for a minute? I think not.

So, we found a one-hour trail ride that could accommodate all of us from age 5 to age 72 just a few miles from downtown Jackson at Spring Creek Ranch. At just $49 per person, it was actually a pretty solid deal as far as equine activities go.

(Photo by Summer Hull/The Points Guy)

One hour in the saddle was just the right amount of time for our group and the guide was excellent with our 5-year-old who ended up tethered to him on the trail.

Grand Teton National Park

If you make it to Jackson, you absolutely need to make the 20 minute drive over to Grand Teton National Park. I recommend a stop at Creekside Deli on the way out of town to secure a picnic lunch to enjoy in the Tetons.

(Photo by Summer Hull/The Points Guy)

After fueling up on our chips and sandwiches at picnic tables, our crew hiked around String Lake then drove around the park where we spotted some wildlife — including a bear — from our vehicle. While we didn’t do it on this trip, booking a float trip down the Snake River can also be a lot of fun, too.

Another easy spot to get to via car is the Mormon Row area to see some historic homesteads and barns. These usually photograph best in the morning but are worth a stop whenever you can make it by.

Moulton Barn, Grand Tetons, Jackson Wyoming
Moulton Barn at the base of the Grand Tetons in Jackson Wyoming. (Photo by strickke / Getty Images)

If you are into historic structures, the Chapel of the Transfiguration within Grand Teton National Park is worth at least a few minutes of your time.

For us, getting into the national parks on this trip came at no cost thanks to my dad’s lifetime senior National Park Pass that he bought when it was just $10 several years ago. That pass is now $80, which is still an excellent value. However, my kid’s 5th grade national park pass would have also done the trick (extended from 4th grade due to the pandemic).

Related: How to visit national parks for less

Virginia City

Just 20 miles west of Yellowstone National park (though it’s 90 miles by car), sits Virginia City, Montana. As the town describes it, this is a ghost town that is still very much alive.

Virginia City hit its heydays in the mid-1800s when mining boomed in the area, but as the gold dried up, the town became frozen in time where it still sits in the Victorian era.

Virginia City. (Photo by Summer Hull/The Points Guy)

Today in Virginia City you’ll find the oldest operational Opera House west of the Mississippi, tours, a fun gem panning experience, a saloon and a small train that runs 1.5 miles from Virginia City to Nevada City. The price for a train ride for adults was $10 per round trip and kid tickets were $8.

(Photo by Summer Hull/The Points Guy)

We stopped in Virginia City for a few hours while heading from Jackson to Butte, which felt like the right amount of time for our group. While the heat made it a bit tough to fully enjoy, we had fun on the train ride, eating some huckleberry ice cream sandwiches and peering into the old buildings.

The kids also really enjoyed panning for garnets and gems near Nevada City ($10 per panner).

(Photo by Summer Hull/The Points Guy)


After an hour or two of driving from Butte towards Glacier, we needed a stretch break and stopped in Missoula. This was one of those lovely surprises which turned out an even better than expected car break.

Luck was really on our side, and we happened to be going through around lunchtime on a Wednesday in the summer. This meant that around a dozen food trucks were lined up in Caras Park in downtown Missoula right next to the spectacular Dragon Hollow playground that was our original reason to stop.

(Photo by Summer Hull/The Points Guy)

Even if you don’t strike lunchtime gold with the presence of food trucks, little kids should have a great time at the Dragon Hollow playground with its many multi-story structures full of nooks and crannies.

(Photo by Summer Hull/The Points Guy)

Watching some men and women try their hands at surfing and kayaking on Brennan’s Wave from the bank of the Clark Fork River that runs through this same downtown area became the extra cherry on the experience.

With the exception of the $20 or so we spent at the food trucks for assorted items for lunch, this was a few hours of memorable, and free, entertainment.

Glacier National Park

If I had to pick a singular headline of the nine-day vacation, it was hiking, swimming and exploring in Glacier National Park.

We dedicated multiple days to exploring various parts of Glacier and it lived up to the hype, offering something for all of us.

(Photo by Summer Hull/The Points Guy)

We went early in the season, so this meant that the Going-to-the-Sun Road hadn’t yet fully opened since that doesn’t usually happen until late-June or early-July. This resulted in some additional driving time to get from the west to the east side of the park, but it also likely resulted in a little less demand and slightly lower lodging prices since it wasn’t yet peak season.

Glacier is not Disneyland. These are real trails with changing conditions and very limited cell service to bail you out in the event something goes amiss. However, don’t let that scare you off — just be prepared as you head in.

Some of the family-friendly Glacier hiking trails we enjoyed included:

  • Three Falls Trail
  • Trail of the Cedars
  • John’s Lake Loop
  • Avalanche Lake

Of those, Trail of the Cedars is the easiest and shortest at just a one-mile loop. It’s also wheelchair and stroller-friendly.

Avalanche Lake was the toughest hike we did and it took multiple hours and had some pretty legit incline at times. It was doable even for our 5-year-old, but required frequent breaks and lots of water, so plan accordingly.

(Photo by Summer Hull/The Points Guy)

The payoff at the top when you reached the lake was absolutely worth it. You can read more about these hikes and the current entrance and reservations requirements in our Guide to Visiting Glacier National Park.

It wasn’t all hiking for us in Glacier. In addition to the scenic drives we took, we also really enjoyed spending time around and in Lake McDonald in the Apgar Village of West Glacier. There we enjoyed ice cream, a restaurant, shops, picnic tables and the lake itself.

(Photo by Summer Hull/The Points Guy)

Float trip on the Flathead River

There’s only so much ground you are going to be able to cover in a national park on foot when little kids are in the mix, so we decided to let Mother Nature do most of the work via a half-day scenic float trip with the Glacier Raft Company along the Flathead River in West Glacier.

This was the priciest activity of the trip at $65 per adult and $55 per child (prices go up a little during peak season from July 1 – Aug. 10), but it was certainly worth the cost.

At around two hours on the water, it was the right length of time for a younger family and it had a few small rapids to keep the excitement level up a bit. My 11-year-old is probably ready for the whitewater option next time, but this was the perfect intro to rafting for the 5-year-old.

If you do this float, it’s helpful to know upfront that everyone was required to change into wetsuits. We were almost late for the bus that took us down to the river as there were limited changing areas and the wetsuits weren’t the easiest for kids (and adults!) to get in and out of on their own, so plan ahead and allow plenty of extra time.

Overall impressions

After canceling most of our plans in the summer of 2020 and opting for short, local adventures during that phase of the pandemic, we were ready to embark on a bigger, longer family trip this summer.

In nine days, we covered a lot of ground across three states and were able to experience several distinct cities, areas and even climates.

To balance out costs, we used a mix of hotel points, a whole home rental, inexpensive lodging options and the unique glamping experience. This kept our per-night average lodging cost within our budget since some $0 of out pocket nights when using hotel points helped to offset out the pricier glamping or home rental nights.

Thankfully, outside of the horse ride and raft trip, our activity costs were pretty minimal since we were just exploring national parks using a lifetime pass. And since we usually picnicked one to two meals per day, food costs weren’t too terrible either.

But costs aside, after a year with way too much time stuck inside staring at screens, resetting in the vast outdoors where breathtaking waterfalls are more common than a good cell signal was the perfect way to usher in summer.

(Photo by Summer Hull/The Points Guy)

Not only was what we saw and did rejuvenating, but since my family was pretty cautious throughout the pandemic, we didn’t really even much spend time with my parents before all the adults were vaccinated. So, this trip wasn’t just about catching up on the mountains we’ve missed, but we were really also catching up with each other.

(Photo by Summer Hull/The Points Guy)

After around 365 days of staying more apart than together, these 1,098 miles on the ground through a gorgeous part of the country proved to be the right family journey at the right time.

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