How to Plan a Family Trip to One of America's Most Glamorous Mountain Towns
Aspen's mystique is palpable –– it's seen outside Paradise Bakery where snow bunnies sip morning cappuccinos, heard by the off-key belting out of "Sweet Caroline" at Cloud 9, and tasted in Hotel Jerome's infamous prohibition-style spiked milkshakes. As a parent, the experiential learning philosophy resonates for me and it is all about the mix to raise well-rounded children. While I love adventuring to the remote and unknown, and Aspen is not down a dusty dirt road, it is the essence of the symbiotic lifestyle.
I have been accused of being too curious about too many things all at once (but really, how does anyone not want to know and embrace everything around her?). Still, guilty as I am, Aspen is my kryptonite. If you are heading to this snow-globe of a town in winter, I have some sympathy for you –– there are truly so many winter activities, après-ski options, and delicious restaurants in Aspen that it can feel overwhelming.
Après-ski is to Aspen as tea time is to Brits, so for proper pomp and circumstance of this pastime, head to The Little Nell's Ajax Tavern for hot chocolates the size of your head with house-made marshmallows, country club–sized pours of pinot, and trays of truffle fries. Even on the busiest week of the year, we managed to find tables for our crew and just sort of piled in for an après session.
Walking into the Hotel Jerome is stepping into a John Wayne diorama, the site of Hunter S. Thompson's infamous Sherrif Campaign headquarters. J-Bar serves an "Aspen Crud," a Bourbon Milkshake created during prohibition so when the law walked in, patrons would appear to be drinking ice cream milkshakes rather than the boozy beverage.
There is romance in the solitude of a snowy walk, and somehow the snow keeps even the birds in a deep sleep. It is as quiet as a library and is my favorite time of day to grab a morning pick-me-up for the tots back at home, while also getting my dose of "me" time. Jour De Fête is my go-to for this purpose exactly –– it's family-owned, opens early (6:30 a.m.), and makes the perfect hot cocoa and croissants to bring back to the chalet for sleepy heads.
Paradise Bakery's fresh-baked muffins and breakfast burritos make for a delightful morning haul. Pro tip: Make sure to snag a bag of the mini cookies (pure convection perfection) because vacation math means five mini cookies = one regular cookie.
Poppycocks is Aspen's local diner. The kids rated the Mickey Mouse pancakes the best in town (though my personal vote goes to the oatmeal pancakes at Bonnies on Aspen Mountain) and you can get in and out in 45 minutes, which, in the morning madness to the slopes, deserves some sort of prize.
Normally, my human body is 60% water. After a week in Aspen, this percentage is mostly The Big Wrap's Pesto Wrapture (grilled chicken, brown rice, salsa, poblano cilantro, cheese, and sour cream). The chicken caesar salad is also the perfect ratio of salad to dressing. After a day on the mountain, the kids' favorite après-ski is a wrap from the Little Wrapscals menu on the couch with "Encanto." I don't make it to the couch, as I have already promptly inhaled my wrap in the car at this point after picking up our orders.
One of my many parenting errors was introducing our children to sushi. At the time, we thought it was clever to introduce their palates to a wide variety of flavors. What we didn't take into consideration was that they body sushi rolls and suddenly our spend per head at family dinners has quadrupled. C'est la vie. Matsuhisa Upstairs is casual and perfect for early kids dinner of avocado rolls, edamame, and mochi ice cream.
Meat & Cheese is my top pick for takeout, namely their roast chicken for tired kids. Pro tip: Delegate dinner pickup duty to yourself and wiggle to the back bar for a Meat & Cheese Board for one while you wait for your order to be ready.
Ice skating makes me feel like I'm 9 again, and as someone who loves to tap into her inner child –– and also share these moments with her children –– this is always a delight. If there is an ice rink in heaven, it will be modeled after Aspen's ice rink, complete with CP Burgers and chocolate milkshakes.
Skiing Buttermilk with your kids is one of life's sweetest moments. Few things bring me as much joy as squealing down the mountain with our kidlets. How very Aspen to have the most posh open-to-the-public Recreation Center replete with waterslides, spouting fountains, and a jacuzzi for local nattering after a day on the slopes. There is something calming and nostalgic about the smell of an indoor pool that feels like a small-town comfort blanket. The lazy river was a welcome respite after a day whizzing down the slopes.
Pine Creek Horse Sleigh is a charming adventure if you need a day off from skiing. If everyone needs a break from their ski boots, book a horse-drawn carriage for a snowy wonderland journey to lunch at Pine Creek's log cabin wonderland.
We want to see it all, do it all and embrace it all, and this battery ram of excitement scores low on the vacation relaxation scale. We subscribe to the Alain de Botton school of thought in that: "The pleasure we derive from journeys is perhaps dependent more on the mindset with which we travel than on the destination we travel to."
And so while I invited Aspen to delight me with Caribou Club cocktails and Belly Up boogies, we also proactively carved out time for solo morning walks in the snow, cheese board chats, and lazy river floats to give us the nourishing balance we needed and the family connection we craved.