Jenny Lake at Grand Teton National Park, Jackson Hole in September

A Spectacular 4 Day Jackson Hole Itinerary in September

Our trip to Jackson Hole was such a pleasant surprise. We were gifted the trip from Chick-fil-A after competing in their yearly Operator Sales Contest. (If you’re new here, my husband is a Chick-fil-A Owner/Operator). We would be visiting Jackson Hole in late September–this meant cooler temps and fewer crowds! While I wanted this trip to be relaxing, I also wanted to take advantage of the scenery and wildlife.

Keep reading to discover all the things we did and why visiting Jackson Hole in September is the best…

Related Posts:
Jackson Hole in September Travel Guide
Jackson Hole to Yellowstone Day Trip

4 Day Jackson Hole Itinerary

We were in Wyoming a total of 6 days, but I chose not to include the travel days in this itinerary. If you’re traveling to Jackson Hole from the east coast, you’ll likely have a full day of travel.

Day One: Grand Teton National Park

If you’re traveling to the Tetons from a place of a lower altitude like Florida, take the advice others tried give me and wait 2-3 days before hiking. I didn’t think the altitude would really affect me, but I had a headache for 3 days. It was also hard to sleep and it can be hard to catch your breath.

Please also know, we didn’t do that much hiking. I did some quick research and knew I wanted to go to Jenny Lake. Jenny Lake Boating offers one way transportation or round trip across the lake, so you only have to hike 1/2 a mile to see Hidden Falls. If you were to do one-way, the hike is about 2.5 miles back. They only provide services between May 15th to September 30th, which is why we opted to visit Grand Teton National Park on our first full day.

After visiting Jenny Lake, we drove around to some other sites including Mormon Row, Mt Moran, and other lookout areas. We spent about 3 hours in the park before heading back to our resort. You could easily spend a full day in the Tetons. There are numerous hikes and of course, plenty of wildlife to see.

John and Brittney Naylor standing beside the Grand Teton National Park sign in Wyoming
Jenny Lake and the Grand Teton mountain range
Grand Teton National Park trees and mountain rocks

Day Two: Yellowstone National Park

On our second day, we booked a tour with Yellowstone Day Tours. It’s a FULL day tour and they provide hotel pickup from most hotels in Jackson Hole and Teton Village. They also provided breakfast and lunch for us.

Doing a day tour to Yellowstone was such a great thing for us for many reasons. For one, we didn’t rent a car. We also knew very little about Yellowstone and it was great to have a tour guide to offer history and drive us around the lower loop. If you’re interested in learning more about the park and its wildlife, I highly recommend scheduling one of their tours. They provide an informative and engaging experience.

We were able to see Old Faithful, Artist Point, geyser basins, and more! We also saw a TON of Bison, some prong-horned deer, and moose.

Old Faithful in Yellowstone National Park
bison roaming in yellowstone national park
artist point in yellowstone national park

Day Three: Aerial Tram in Teton Village

On day three, we slept in a little bit and then walked to the arial tram in Teton Village. The aerial tram takes you to the top of Rendezvous Mountain where not only can you see some spectacular views, but you can eat waffles! An aerial tram holds up to 100 people and it’s about a 12 minute ride–though it definitely didn’t feel like it. You can also paraglide or hike from the top of the mountain.

I’m also not one to eat waffles, but opted to try some that included peanut butter and bacon–I loved it. John had classic waffles and he was a big fan, too.

Chick-fil-A had activities planned for us that afternoon, so we didn’t plan anything else for day three.

Check out some of our favorite places to eat in the area.

John Naylor on the top of rendezvous Mountain in Jackson Hole, Wyoming
waffles on the top of rendezvous mountain in jackson hole wyoming

Day Four: Jackson Square

Jackson Square is probably the cutest little downtown area I’ve ever seen. It’s filled with plenty of shops and restaurants to enjoy. We ate lunch at Teton Hand Fire Pizza, which use to be an old movie theatre. It was really great and a great change from bison burgers. I also grabbed a fabulous latte from Cowboy Coffee. During our day trip, we had discovered that huckleberry flavored anything is really popular in Wyoming, so we bought some goodies back home.

Jackson Square also has 4 beautiful arches that were built using the antlers from elk. Don’t worry, the antlers actually fall off the male elk every winter. After a few hours in Jackson Square, we went back to our resort to enjoy some football and begin the task of packing everything for our return home.

teton in red letters and marquee, hand fire pizza
Jackson Square Elk Antler Arch, John and Brittney Naylor standing together underneath, Jackson Hole in September

4 Day Jackson Hole Itinerary: Conclusion

Visiting Jackson Hole in September was truly a magical experience. It was definitely a change of scenery from our typical Florida landscapes and we thoroughly enjoyed our time. We are so blessed to be a part of Chick-fil-A and love that they do trips like this for us.

I hope this 4 day Jackson Hole itinerary helps you as you plan your trip out west. Even if you just decide to take in the views and watch the wildlife, it’s an unforgettable experience.

Have questions about Jackson Hole in September? Leave them down below and I’d love to help!

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4 Days in Jackson Hole, Wyoming for Couples

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Leave a Comment

The Comments

  • Saunter With Sanika
    March 27, 2023

    I absolutely love exploring nature parks, this would be such a wonderful weekend away!

    • Brittney
      → Saunter With Sanika
      March 27, 2023

      Still can’t get over all of those amazing views!

  • simplyjolayne
    March 27, 2023

    Where is the escape next year for Chick fil A? Congrats! Glad you were able to enjoy your time.

    • Brittney
      → simplyjolayne
      March 27, 2023

      It will be in Hawaii, but unfortunately I don’t think we’ll be winning this trip. At least we have our own Italy trip to look forward to this summer!

  • Sierra
    March 27, 2023

    What an amazing trip…September looks like a great time to visit! Your pictures are amazing. Thanks for sharing!

    • Brittney
      → Sierra
      March 27, 2023

      Yes! The weather was perfect and the crowds were minimal.

  • Bre | Somewhere With a Suitcase
    March 27, 2023

    Wow!! This post makes me want to visit Wyoming even more! The pictures are absolutely gorgeous! Saved this to reference for my future trip out there, thanks for all the information!

    • Brittney
      → Bre | Somewhere With a Suitcase
      March 30, 2023

      Thank you so much! I hope you get to visit one day!

  • Jillian
    March 27, 2023

    Great information! I’ve been wanting to do a Wyoming trip for years now but never realized how much can be done in 4 days! Hotels always seem on the pricier side but I’ll have to look for September now!

    • Brittney
      → Jillian
      March 27, 2023

      There are so many resorts/hotels to choose from! You could also look into Airbnbs too!

  • Jennifer Femrite
    March 27, 2023

    Your photos are beautiful! I’m definitely adding Jackson Hole to my travel bucket list! Thanks for the tips and advice.

    • Brittney
      → Jennifer Femrite
      March 28, 2023

      Thank you so much! It’s such a beautiful area and it was such a treat for this Florida girl.

  • Leah
    March 28, 2023

    Wow, your photos are beautiful! Wyoming is so high up my travel bucket list!

    • Brittney
      → Leah
      March 28, 2023

      Thank you so much! Wyoming was such a magical and beautiful destination! So glad we had the opportunity to visit!

  • wanderwithbelle
    March 30, 2023

    I would love to visit