About

Jackson Hole, Wyoming is an incredible place to vacation all times of year. With stunning scenery, wildlife galore, and an endless array of outdoor activities to enjoy by day, with fine dining and unpretentious “watering holes” by night, you can’t goo wrong coming here for a vacation. Nestled near the gorgeous Teton mountains, the natural environment lends itself to skiers, snowmobilers, fisherman, hikers, rafters, and more. I’ve only been during the winter, but it’s on my bucket list to check things out in the warmer months too.

How to get there

From Chicago, you’re going to want to fly in to Jackson Hole, WY. You can fly direct, and it’s a pretty quick flight! The Jackson Hole airport could very well be a five star resort with the views, the couches, the fireplaces. It’s giving luxury cabin energy in a big way. Once you’ve arrived, you may or may not want to rent a car. You can take a quick Uber to wherever you are staying, if you’re staying downtown there are shuttles up to the mountain for skiing. If you are staying on the mountain, you can certainly Uber after hours to the lively city restaurants, etc. but for skiing / outdoors vacations, I always find it a bit more convenient to have my own wheels. Since it’s a mountainous area, opt for something with four wheel drive if you are headed there in the winter.

Know before you go

From Chicago, this is one of the most straightforward ski vacations you can book. Yes, it’s a little pricey. Yes, JH is known for being a challenging and steep mountain to ski on, but honestly, being able to fly in, fly out, not having to rent a car, and getting the best of the best from an amenities perspective… it’s a wonderful spot and I highly recommend it!

Eat

Coffee — Persephone Bakery is the most adorable spot in Jackson for coffee and croissants. Enjoy the glorious sun-drenched cafe for your morning journaling, reading or time away from the madness of your ski vacation.
Lunch — Head to Mangy Moose at the base of the mountain for bar vibes and to make friends with the table next to you, or for something a bit more boujee (and with a view!) for the girlies, head up the Bridger Gondola and grab mimosas at Piste Mountain Bistro.
Dinner — Local has incredible food and craft cocktails. Head here for Manhattans, Dirty Martinis, and fresh Oysters, their rainbow trout, and their rabbit pappardelle, holy sh*t so good.
Drinks — Million Dollar Cowboy is the real one. Excellent vibes here. Saddle up to the bar and take a few pickleback shots for me.

Stay

We stayed in an Airbnb on our last trip, and I think for a big group, this is the way to go. There are tons of great options, and with all the gear you have to tote around for a ski vacation, plus the desire to have a non-hotel bar place to hang out with your friends and family when you get off the mountain, I think it’s the way to go. You’ll have to decide to stay on the mountain or downtown… If it were me, I am staying downtown :)
The Caldera House is next-level stunning, and next level pricey, but if you’re looking for an epic getaway, and a mountainside stay, this is the spot for you.
I haven’t stayed at The Cache House but this is a boutique-hotel-meets-hostel-style-property where you can get a room for under $100/night during ski season downtown Jackson. The catch? You’re sharing a room with other travelers… But honestly, I’m not mad about it. Travelers in Jackson Hole are there for one reason — they love the great outdoors as much as you do, and they are probably cool as hell. Bonus — it’s a 3 minute walk to Local and Million Dollar Cowboy Bar.
I haven’t stayed at the Fireside Jackson Hole but I discovered it recently and thought the little cabins looked cute and I’d enjoy going there for a romantic getaway, perhaps during hiking (read: not ski) season. It’s about 10 mins to the mountain and about 10 mins to heart of downtown.

Workout

You are on a ski vacation, what more do you need than the vacation on the mountain??? That said, I always love to check out a yoga class when I am in a new city, especially if I’m going skiing or snowboarding because let’s face it, I’m no spry chicken these days. If this is you too, head for yoga and sound baths at Home Yoga JH.

Play

Skiing — Jackson Hole Resort is the place to be. If you are an Ikon pass member you can ski here to your heart’s content. If you know an Ikon pass member, they can get you special discounts here. If you are neither, you’re looking at $225 for a weekend ski lift ticket, and they do sell out, so grab yours in advance.
Dog sledding — Call of the Wyld is female-founded and offers 45 min tours, plus is at the base of the mountain. There are other dog sledding outfits in town, but honestly 45 mins is a wonderful amount of time for this activity. Most other places require 6 hours or more. I don’t know about you, but I’m always apprehensive to give up half a day to an activity I’m not sure I’m going to enjoy. We had a ton of fun with the Call of the Wyld team, but for us 45 mins on a dog sled was just perfect.
Snowmobiling — You can rent snowmobiles or book a tour, but I think renting is the way to go! Rent from JH Adventures and make your own adventure. Ronnie and I wanted to take a trip to a hot spring, so we rented the sleds, and a trailer, and drove about an hour outside of JH to the Granite Creek Trailhead to see the Granite Creek Hot Springs. We packed bathing suits, towels, and snacks. When we made it to the hot spring, we were pleased to find they had facilities for us to change and whatnot from our snowmobiling gear into our swimwear.
Spa — An alternative to skiing and day drinking, head to any one of the hotel and resort spas to be pampered, I hear the four seasons is nice, but I’d recommend the one at the Caldera House, so you can meet up with your friends on the mountain after. If you’re feeling more of a DIY spa day, book with Jackson Mobile Massage and get a concierge IV from Reméde.

Sound bath — As another alternative to skiing and day drinking, Home Yoga offers sound baths from time to time, so you can drop in, relax, meditate, and head back to your ski friends with a sounder mind. If you haven’t ever done a sound bath, first and foremost, you should. Why? It’s been explained to me this way: the way sound vibrates, creates an experience where you basically get a fully body massage, but on a cellular level. Oh yeah, it’s gooooood. I am a huge fan, and when I was living downtown Chicago, I would get one about once a month, so this is totally worth looking into!
Shopping — Jackson Hole has cute boutiques all over downtown. You can park near Million Dollar Cowboy and walk around from there. Lots of places to pick up souvenirs, unique clothing or jewelry, and anything else your heart desires!

A Dream Day

If I had one day in JH and realllllly wanted to pack it in, here’s what I’d do…

Wake up at Caldera House and head straight to your spa appointment — get a massage and a facial and bask in how good it feels to be on vacation. After you’ve had worked up an appetite from your pampering, head to Persephone for coffee and breakfast, bring your journal so you can write your thoughts about how beautiful life is, and how lucky you are to be vacationing in Jackson Hole and how grateful you are for friends that are into the same things you are. Head back to Caldera, grab your skis and get on the mountain! Enjoy a mimosa at the Piste Mountain Bistro at the top of the hill. Check out a multitude of runs, Jackson Hole is known for being steep and challenging, so take it easy and make sure to map out your path down the mountain before you get caught up in a situation you can’t get out of. At the base, head to Mangy Moose for lunch and vibes. If you’re feeling only half day energy, pack it in, and drive yourself to downtown Jackson Hole for some shopping, yoga and a sound bath for your afternoon adventure. Head back to the hotel to shower up and meet your friends back at the mountain for a 45 min dog sledding adventure with Call of the Wyld, followed by Aprés, before heading out for dinner at Local. Local is cute enough, you’ll want your friends to have showered and put on their nicest leggings and sweaters to attend dinner with you. Get a dirty martini, oysters, and the rainbow trout. Pay your bill and walk on over to Million Dollar Cowboy. Take shots, hang out with other vacationers and locals alike, maybe even make some bad decisions like dancing in public (jk, jk). Head home and lay your weary head to rest, you made the most out of your day in Jackson Hole. In the morning, head into Reméde for an IV, you’ll need the stamina for your snowmobiling adventure at Granite Creek/Hot Springs later…

Summary

Jackson Hole is a wonderful place for a trip with your best friends of any gender, your family of all ages, or your girlfriends (assuming your girls ski). From the outdoor enthusiast, to the shopaholic, to the spa girly, there’s something for everyone. Burn your calories by day on an epic adventure, fill up with delicious food and drink by night. You won’t lose any weight on vaca, but you also won’t gain any, lol. Enjoy! I can’t wait to hear what you think about these recommendations!

Jackson Hole, Wyoming