Our Perfect Jackson Winter Weekend

Published on March 01, 2019 - Updated on May 27, 2021

Our perfect winter weekend...

One of the reasons we created Happy Active Family in the first place was because we found that our free time was so scarce and precious, that the thought of wasting any time with endless google searches for ways to spend it seemed like a small tragedy. To spare you the same trouble, I want to share with you what our winter weekends typically look like. Because after 6 years of visiting and a year and a half of living full time in Jackson, I feel like we’ve finally cornered the perfect kid friendly weekend.

When 4pm on Friday afternoon rolls around, I feel myself breathing deeply, a huge sigh of relief coming into the time of week that I cherish the most; family time. A time to unwind and ease into leisure mode, Friday nights we often keep things simple by hanging out at home, making dinner, lighting up a fire and taking in the view of Snow King, because we are all pretty wiped from juggling the weeks activities. Once in a while, if our energy level surprise us, we head to Hole Bowl, our local Bowling Alley. It’s one of our favorite interactive family things to do, with the option to bowl, play arcade games, indulge in cornhole, shuffleboard, pool, or just sit down for some dinner in their intriguing space. It’s good for all ages, clean and a good way to have a great time.

After a generally early night to sleep, Saturday starts with an incredible feeling of gratitude for all of the time we’re about to get to spend together! We call it Baxter day and our daughter knows that it’s my absolute favorite day of the week. If Hanah and I don’t make Jo's Biscuits (and a super beautiful mess), we take it slow and head to Cafe Genevieve for breakfast/brunch. I’m partial to the Egg’s Benedict and our little loves the Waffle with whipped cream and berries (although, the berries seem to get eaten by the grown ups mostly, #momfail lol).

In a post breakfast glee, we start thinking about how we will choose to get active. In the midst of a Jackson winter, these activities often involve SNOW! They range from family skiing in Teton Village and exploring the Teewinot and Sweetwater runs (all day or part day event), hiking around dreamy Cache Creek (about an hour), or walking the Russ Garaman Bike Path (30 to 45 minutes). For us, we love the outside time and any chance to enjoy this glorious playground we feel blessed to live in. In Teton Village, we enjoy hot chocolate breaks and macaroni and cheese from the Handle Bar, some quieter snacks at OYG (sharing the chicken parmigiana sandwich), or some on the go pizza slices, chili, and Swedish Fish (also known as lunch for toddlers) from Off-Piste. No matter how many runs we get in, I always try to pause and enjoy the beauty.

After skiing or hiking, the Snow Castles in Teton Village tend to be a win. We play tag or hide and seek and, for moments, it’s all there is. There’s no rushing to work or other plans. It’s a chance to be present and enjoy. We love the relationships that are growing as we see other families enjoying similar things and special time together. Sometimes we stay for apre ski and indulge in the Spur’s nachos, music at the Mangy Moose (although it can be loud for little ears), or a quiet glass of wine in Hotel Terra’s lobby. As Saturday comes to a close and the last of the family movie night wraps up, I try not to think too far towards Sunday. Although a great part of the weekend, it’s a bit more scheduled and closer to the work week.

It’s easy to shake off the Sunday Scaries though, when we arrive to the Village and prepare to ski the day away. We participate in a locals ski program and feel super lucky for it. I struggle a little because I want the time with my daughter but I also marvel at the confidence she’s gaining from the program. I also try to soak in the time together before, during (as I cruise the green and blue slopes looking for her little smile and hoping she’s having fun), and after (where she usually ends up curled up in my lap with sleepy but proud eyes). If we are super lucky, after pick up, we get to do a few runs together as a family to celebrate the new learnings and to try out the new trails that were explored that day; Princess Woods, Squirrel Woods...the list goes on. The pride our sweet human feels for trying new things makes me feel okay with missing out on those few extra hours together.

One of our new favorite post skiing activities on Sunday’s is the band at Alpenhof. There’s nothing like live music and great happy hour deals to celebrate the ski day! It’s fun to see the little’s dancing to the chicken dance and sharing in the collective enervation of happy, and humbly tired skiers. Back in town, Sunday dinner at home is my favorite. If we have company though, we love Teton Tiger (great kids noodles with veggies they will actually eat), Local for burgers, macaroni and cheese bites, or kids pasta (bar area only), or Snake River Brewing (although we are somewhat partial to summer nights there because of the ability to stay outside and soak in the views and lawn games). Before we know it, it’s time to leave, and just like that, a great weekend has been had by all.

There’s so much to explore, enjoy and to appreciate in our beautiful little mountain town. If we can ever be of assistance as you’re planning your family vacation to Jackson, please reach out to us at team@happyactivefamily.com

Thoughtfully captured by:
Caitlin Iseler
Caitlin Iseler, happyly founder and CEO, was born in New York and is one of eight children. Her favorite holiday is Thanksgiving and the chance to sit at one table with her favorite 40 people. Caitlin, her outdoor loving husband, Thomas, and daughter, Hanah, live in Virginia Beach. She is also blessed to be a bonus mom to 2 incredible humans, Max & Elizabeth. Being a mom has always been something she dreamt of and it brings her joy beyond measure. Before starting happyly, Caitlin spent 15 years working in executive search with technology companies, most recently with Korn Ferry. In what seems like a lifetime ago, she attended the University of Virginia and was a member of the National & ACC Championship Teams, a gift that keeps giving.
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