The Ultimate 5-Day Grand Teton, Jackson Hole, & Yellowstone Itinerary (And the Mistakes to Avoid)

Planning a trip to Grand Teton and Yellowstone National Parks can feel overwhelming. They are massive, crowded, and require a ton of logistics. I spent five days exploring both in late September, and while it was an incredible trip filled with wildlife, hiking, and beauty, I learned a few major lessons along the way.

🛑 The #1 Mistake I Made: Our Lodging Choice

Before we dive into the daily breakdown, let’s talk logistics. We stayed in Driggs, Idaho. To put it bluntly: it was far as hell from Yellowstone. Since Yellowstone is so massive, staying on the Idaho side forces you to spend hours commuting before you even get to the park. However, we were more focused on the Tetons, so for that it worked out.

My Pro Tip: If I were to do this trip again, I would recommend booking two separate Airbnbs. Spend a couple of nights closer to Jackson Hole for your Grand Teton days, and then move up to a spot closer to a Yellowstone entrance (like West Yellowstone or Gardiner) for the rest of your trip.

Day 1: A Relaxing Introduction to Grand Teton

Heron Pond/Swan Lake Hike

We kicked off our trip on September 20th by heading into Grand Teton National Park. Since we were adjusting to the area, we kept things relatively light, especially after a day of travel.

  • First Stop: Colter Bay Visitor Center. This is a great spot to grab a map, talk to park rangers about trail conditions, and stretch your legs. We also saw a moose here, just hanging out!
  • The Hike: We opted for some very chill, flat hikes around Heron Pond and Swan Lake. It’s a peaceful loop that gets you away from the heaviest crowds and offers great birdwatching. Also, the views are just absolutely beautiful!
  • The Afternoon: We spent the rest of the day wandering around the town of Jackson Hole, exploring the local shops and checking out the famous elk antler arches before making the long drive back to our base in Idaho.

Day 2: Our One-Day Yellowstone Blitz

Yellowstone is a lot of driving from one point of interest to another. It isn’t really the kind of place where you park once and hike to every spot. You will be hopping in and out of your car all day. It is also incredibly crowded. Even visiting in late September, the park was super busy! Everything is so accessible via paved pathways and boardwalks, everyone wants to see it. Which is awesome, but you need to pack your patience.

Grand Prismatic Basin, zoomed in from the overlook trail

Must-See Stops:

  • Grand Prismatic Spring: Walk the main boardwalk to see the vibrant colors up close. But if you’re feeling up for it, do not skip the overlook trail. Walk up the hill behind the basin on the Grand Prismatic Overlook Trail. It’s a short, easy-to-moderate trail (under 2 miles total) with a gentle incline. The aerial view of the spring from the top is worth the extra steps.
  • Scenic Viewpoints: Take your time driving the main loop and pulling off at the marked vistas. The canyons and thermal features change around every corner.
  • Old Faithful: You can’t visit Yellowstone without seeing its most famous geyser. Cell service is practically non-existent in the park, so if you are traveling with a group, make sure you establish a designated meeting spot beforehand. The Old Faithful eruption schedule is posted all around the visitor centers, and if you happen to catch a stray bar of service, it’s updated regularly online.

🗺️ Planning a longer visit? If you want to expand your Yellowstone adventure, check out my custom 3-Day Yellowstone Points of Interest Map to help plan your routes.

Day 3: Cascade Canyon, Inspiration Point, and Wildlife

September 22nd was easily our best hiking day of the entire trip. We drove over to the Jenny Lake Visitor Center early in the morning to secure parking.

Cascade Canyon

The Jenny Lake Shuttle Hack

There is a boat shuttle that runs across Jenny Lake which can cut about 4.5 miles off your total hiking distance. We weren’t able to take it on the way in because it doesn’t run super early in the morning, and we wanted to beat the crowds to the trailhead.

Instead, we hiked around the lake following this AllTrails route. Taking the long way gave us the opportunity to see:

  • Hidden Falls — A beautiful, rushing 100-foot waterfall.
  • Inspiration Point — A steep but rewarding climb that offers sweeping views across Jenny Lake.
  • Cascade Canyon — We didn’t do the entire grueling trail, but we hiked a good portion of it. The canyon walls towering over you are humbling.

To end the day? We took the ferry back across the lake at the end of the day! Skipping that final 2-plus mile walk back saved us some serious time and foot ache.

Wildlife Safety: We saw so many moose on this day, which was absolutely incredible. Please keep in mind not to approach or be on the path of these animals. On that same note, this is also active bear country. Always, always carry bear spray where it is easily accessible (not buried inside your backpack), and know how to use it.

A moose near Cascade Canyon

Day 4: Jackson Hole Mountain Resort & Local Eats

After a heavy hiking day, we dedicated the next day to relaxation and food. We headed over to the Jackson Hole Mountain Resort and took the ski lift up to the top of the mountain. There are a few small alpine trails at the summit where you can stroll around and enjoy panoramic views of the valley without any strenuous climbing.

View from the top of the ski lift

We spent the rest of our afternoon and evening eating our way through town:

  • Jackson Hole Winery: A gorgeous spot to sit back, sip some local wine, and unwind.
  • A lot of the restaurants we visited unfortunately closed during COVID. I encourage you to walk around town and stroll into places! There are so many interesting places to eat and try!

Day 5: Horseback Riding in Big Sky Country

You can’t spend a week near Montana without getting on a horse. For our final full day on September 24th, we booked a trail ride and it ended up being one of the highlights of our entire vacation.

We had the absolute best experience with Rockin’ M Horseback Rides. The guides were fantastic, the horses were wonderful, and riding through those wide-open western landscapes was the perfect way to wrap up our trip.

The end of our Montana Adventure

Reminder – At Night

Don’t forget to look up at night! If you’re from a big city, you will probably never see stars like this! It was my first time seeing the Milky Way and getting some practice with astrophotography.

Milky Way!

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