Beautiful views, quaint-but-lively downtown, adventure filled, balanced.

That is how I would describe our 5-day trip to Jackson Hole, Wyoming. The weather early September forecasts clear skies, chilly mornings (lows of 35 degrees), and beautiful sunny afternoons (highs of 75 degrees). We are the type of people who love a vacation with a healthy balance of activity, adventure, and relaxation; Jackson checked off all those boxes for us. Not to mention we had great company along the way!

CLICK HERE to jump to screen shot-able suggestion lists of this trip.

This past Labor Day, we took a trip with another one of our couple friends up to the beautiful state of Wyoming, and let me say, it did not disappoint! This was an adult-only trip, so while there are kid-friendly activities mentioned, and though we did see a lot children shredding the trails, be forewarned that this is not a “How-to-Survive-Jackson-With-Children” post. (Jackson is definitely a place I will return with children-it would be a great time!)

Jackson and Jackson Hole can be used interchangebly. Jackson is the name of the main town located at the southern end of Jackson Hole; while Jackson Hole refers to the whole valley, and includes Jackson, Teton Village, Wilson, and the surrounding areas.


Below you will find suggestive day-by-day itineraries based off how we spent our time, but there is so much more to Jackson that we didn’t get to see, so I highly suggest booking a couple things in advance, but overall letting the adventure and town guide you!

Sidenote: The Yellowstone National Park entrance is approximately 1.25 hours from Jackson; however we opted to save that trip for another time because it takes an additional hour driving inside the park before you reach any points of interest. Be aware that a day trip to Yellowstone is possible, but you need to start your day EARLY.

COVID-19: As of our trip dates, the state did not require masks in public/outdoor spaces unless decided by the business; however, majority of businesses and restaurants require masks upon entry, and will provide them if you do not have one with you.

Day 1

Fly out in the morning or early afternoon.

There are two options when it comes to airports near Jackson: Jackson Hole Airport/JAC (15 min drive into town) and Idaho Falls Airport/IDA (1.75 hours into town). JAC is a smaller airport, while IDA is the larger airport. JAC is more expensive to fly into; however, we chose to fly into JAC strictly because this was such a short trip for us and we did not want to spend a good portion of our day driving from the airport.

Be sure to bring a mask, because federal requirements state that you must wear one at all times in the airports/on the airplane.

Pick up a rental car at the airport

Jackson does utilize Lyft and Taxi’s (Uber is here, but not as prevalent), many hotels provide shuttle services, and downtown is extremely walker friendly, so you definitely can get around without a rental car-but if you are planning on taking any day trips, get a rental. (For reference, a 30 min taxi ride from downtown up to Teton Village will run you about $45 one way). We used Enterprise and were able to pick up our car right at the airport, which was a super easy/quick process given that we flew into the smaller airport and had virtually no wait time.

Check into your hotel

I highly recommend staying in a hotel/resort downtown during the summer months in Jackson. It’s extremely walker friendly, the shops/restauraunts are localized here, and its adorable. I think Teton village would be perfect for a winter stay (ski in and ski out resorts), but downtown during this time of year could not be beat.

Because we are Marriott members, we stayed at the Cloudveil, which is an Autograph Collection hotel just built off the square. It was very nice, but do not waste any “free suite upgrades” on this hotel—at this location the only upgrade they gave us was a standard king room with a view vs the courtyard view, which was nice, but since we were on the second floor overlooking one of the very popular ice cream shops, we kept the curtains drawn majority of the time for privacy.

The aesthetic of the hotel is beautiful: the location is perfect, each “king” bedroom has a fireplace, the bathrooms were roomy/clean, the Bistro (hotel restaurant/bar) was great, and it does have an outdoor pool/hot tub, as well as a rooftop terrace with fire pits. Our concierge Matt was stellar, and was able to get us exclusive reservations on several occasions. This is a beautiful hotel if you are willing to splurge, it is one of the more pricier hotels in the area. If not, there are several other options to choose from (hotels and AirBnB), but again, I highly recommend staying close to downtown for ease of access, especially if you are taking a shorter trip.

Explore Downtown

We got into town around 3pm and spent our first afternoon roaming the town and shops. There are several local galleries, bookstores, souvenir shops, plus so much more. And don’t forget to take your picture under one of the iconic antler sculptures located around the Veterans Memorial park.

Eat Dinner at Snake River Grill

You will want a reservation for this restaurant, as it is one of the most sought out places in Jackson (many celebrities will eat here when visiting). Come hungry and willing to spend some $$$, because they pride themselves on “over 25 years on the Town Square… [and being] the locals’ favorite fine dining experience… featuring 300 wines and signature cocktails…SRG is a must for fresh, uniquely-crafted New American cuisine.”

The food was pretty good, and my personal favorite item we ordered was the salmon potato pancakes (just try it, its great). Unfortunately, we had a couple of “meh” cocktail moments here, so I would stick to wine.

Grab Ice Cream at Moo’s Gormet Ice Cream

If you happen to have room for more, pop over to Moo’s! Known for their natural sourcing, be sure to try the huckleberry ice cream! In Jackson, you can find huckleberry-flavored everything, so be sure to try it all!

Day 2

Grab Breakfast/Coffee at Persephone’s

Wake up early (or don’t, we know I don’t do early mornings) and head out to coffee/breakfast. If you like characteristic, cute coffee places, Persephone’s is a must. They have amazing baked goods and croissant sandwhiches which you can eat in an outdoor courtyard that makes my garden dreams swoon.

Head up to Teton Village for the Day

Teton Village is a smaller town at the base of the mountain and is popular in the winter month for the convenient lift access, but there is plenty to explore during the summer months as well! It is a 30 min drive from downtown and has beautiful views along the way (you may even be lucky enough to see some moose!) There is plenty to do in this village, and below are some activities members of our party participated in during our day at Teton Village:

  • Ride the Gondola to the top of the mountatain
    • I personally don’t like gondola’s, but the views are amazing during the ride and at the top. There is a restaurant that overlooks the valley, and unfortunately it was closed for a private event the day we went. I would suggest trying to eat there on a weekday to avoid crowds/events.
    • Click here to purchase gondola tickets. (When you buy online you save $7).
  • Hike a trail
    • Once you reach the “top” of the mountain, there are several trails at varying diffculties that will take you to the tip top of the mountain, or all the way to the bottom! We chose to hike Casper Ridge Loop, which was a beginner/moderate loop that took us about 1.5 hours to complete. It was challenging with steep inclines at the beginning, but is doable without any hiking gear. This was hands down the most best view, and worth every second.
    • Click here for a summer hiking trail map
  • Mountain Biking
    • You can find bikes for rent in Teton Village, or can bring your own!
    • Click here for a bike park map
  • Play a round of disc golf
    • Either bring your own or purchase from a local sporting good shop at Teton Village, they do not rent the discs out.
    • The course is free and you can find the map here.
  • Have a light lunch at the Four Seasons Resort
    • They have really good guacamole/salsa/queso, and great cocktails- Try a spicy margarita-you’ll find these on the menu most places because they’re very popular in Jackson! (If you aren’t a “spicy” fan, get it with half regular tequila and half infused tequila to knock the spice down!) Be prepared that this is another finer dining experience and will be a little pricier. If you can, sit outside on the balcony, but don’t worry-the indoor seating also showcases beautiful views.
  • Relax!
    • The base of the mountain has several seating options to just sit, sip a drink, and just take it all in!

Dinner at Local Restaurant and Bar

Located downtown, Local was by far my favorite restaurant of the entire trip. The menu features both classic and specialty cuts of locally-ranched meats and game alongside fresh seafood, shellfish, house-ground burgers, and seasonally-inspired food. (Oysters were amazing!)

Drinks and Dancing at Million Dollar Cowboy Bar

Next door to Local is the town honkytonk hotspot: Million Dollar Cowboy. This is a great time if you love two stepping (they have live performances on the weekends), cowboy hats, and people watching while drinking a cold one. There is a cover fee of $10 to enter.

Day 3

Farmer’s Market

Grab a bite to eat and wander around the local farmer’s market that is set up downtown every Wednesday and Saturday from 8-12. Here you can see I bought a cinnamon roll the size of my face, and it was delicious.

Whitewater Rafting

If you need an adventure, go whitewater rafting down Snake River! We booked through Jackson Hole White Water and we had the best guide! He was very knowledgable, and couldn’t have given us a better experience (I got to “ride the bull” which means you get to sit on the front of the raft and hold on for dear life, laughing and getting soaked the whole time you’re up there!) I do recommend renting a wet suit, the water this time of year is about 60 degrees farenheit, which sounds doable, but it’s COLD. Also bring a set of towels/dry clothes to change into after your float! (Forgive my screenshot, I didn’t want to purchase an unwatermarked photo for $50…)

Burgers and Milkshakes at Jackson Drug

Located on the square, this “drug store” first opened its doors in 1919! You can find the rest of their story here.

Visit the Local Rodeo

The rodeo grounds are located right outside of downtown, and I think they have the best rodeo clown I’ve ever seen. During season, rodeos are every Wednesday and Saturday (with additional dates during July and August) starting at 8pm, with tickets for purchase starting at $34. (Reserve/purchase your tickets from jhrodeo.com to avoid major third party upcharging).

Day 4

Breakfast at Cafe Genevieve

Great coffee, great food, cute atmosphere and quick service.

Race Down Snow King Mountain

Located just outside downtown at Snow King Resort, there is Snow King Mountain, where in the summer is full of activities including an alpine slide, mountain coaster, mini golf, ropes courses, and much more!

Round of Golf at Snake River Sporting Club

This is a private club that our concierge was able to work magic to land a tee time for the guys, but if you are able to pull some strings, definitely check this course out. It was beautiful, but I’m also sure that any golf course in this area would be a perfect end to a trip!

Massages and Spa at SpaTerre

This spa is located in Teton Village inside Teton Mountain Lodge. They provide facials, massages, and several other services to choose from as a way to relax before returning to “real life”. *Reserve in advance if possible*

Order in Pizza from Hand Fire Pizza

Rumored to be the best pizza in downtown, and I agree it was pretty good. Our crew decided to stay in, order pizza (picked up by the guys at the storefront) and play boardgames. We ordered a classic pepperoni and a pesto chicken pizza, but you honestly you can’t go wrong with anything from their menu. I couldn’t have imagined a better last night.

Day 5

Grab a quick breakfast at the hotel Bistro, soak up the mountain views, and head up to the airport, crying because you are leaving but looking forward to the day you return. You also could fly out later and squeeze another one of the numerous activities in the Jackson has to offer.

You’ve just skimmed through a snapshot summary of our 5 day visit to Jackson, Wyoming. In between these lines live so many good memories, and I cannot even begin to cover all the great things Jackson Hole has to offer. I even learned that these mountains are highly sought after for their winter slopes, so maybe there will be a snowy return for us in the near future?

Talk soon,

xx, Lanna

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