For Jeff’s birthday, we spent a weekend in Aspen for some fun in the snow. He’s lived in the midwest for most of his life and I spent about eight years in Chicago so we both have a love-hate relationship with the cold weather. However, Aspen is so beautiful and quaint that I barely even noticed the weather. In fact, if I could, I would pack my things up and move there permanently right now (based on my history of frequent moves, that wouldn’t be a huge surprise though).
I mean, seriously, everything about this place is just gorgeous. The mountains are literally surrounding you so it feels secluded and wonderful. Other than staring at the scenery, here’s how we spent our time:
Skiing: Now this isn’t something I would ever do again, but we brought my parents (they don’t love to travel so it felt like a waste of money to me). This way, no one had to ski alone, because someone always had to stay back with the little guy. If your kids are a little older, then you can obviously take them skiing with you, but if not, make sure to find a sitter or travel with a group.
Aspen has four excellent ski resorts to choose from: Aspen Mountain, Aspen Highlands, Snowmass and Buttermilk. We went with Buttermilk because it has options for everyone from beginner to advanced and I’m well… not very advanced. It’s also wise to book ahead of time because you can get cheaper tickets that way and it’s an expensive little town so make sure to budget ahead of time.
Shopping and walking: Downtown Aspen was just a few blocks from the hotel so we were able to spend a lot of time walking around. There are a lot of areas without cars so it was great to get Jimmy out of the stroller and let him run around in the snow (he loved it). Once he tired himself and passed out in the stroller, my mom and I went to do some shopping. Aspen shopping is comprised of primarily two types of shop: high-end retail and art/antiques. Both of these appeal to me so I had a great time checking things out, especially in the art galleries and antique stores.
Dining out: You probably know this already, but Aspen has some amazing food. My favorite was Maru Aspen, a sushi restaurant located under a retail shop. We also had breakfast at the St. Regis most days and that was phenomenal, so if you want to splurge on breakfast, that is a great option. They do an unlimited buffet style brunch which is free for the little ones and it’s a boisterous environment, which is great for kids.
The Hotel: Okay, I’ll admit it: I’m addicted to staying in nice hotels. We stayed at the St. Regis Aspen and it was perfect. The room had a giant outdoor patio (much better in the summertime, but still very appreciated) with an incredible view of the slopes. They have multiple dining options, all were excellent. And my favorite part was the lobby/lounge area at the entrance. It features a central fireplace and a couple dozen seating arrangements, mostly featuring nice, comfy couches. The perfect après-ski scene. Oh, and the hot chocolate was the best, even the adults agreed.
The Travel: So here is where we get to the part that wasn’t great. There are two primary ways to get into Aspen: you can either fly direct into Aspen/Pitkin Airport or you can fly into Denver and then drive in. It was more expensive, but we decided to fly direct because I don’t love the idea of strapping Jimmy into a car seat for three or more hours on snowy, mountain roads (plus, we had the points for it). Well, on the way out, our first flight was cancelled so we actually missed a full day of the trip. Our next best option was to fly into Denver, connect there, and fly into Aspen, so that added quite a bit of travel time. And the return flight was delayed, almost canceled, and then ended up going out, but let me tell you, it is not fun to have little ones at the airport during delays when it is freezing outside (you board the planes outside there).
Aspen certainly would not top my list of kid-friendly cities to visit (at least in the winter), but it would be very close to the top of my overall places to visit. So, if you’re up for the challenge of a potentially terrible airport experience and your kids enjoy the snow, this is a pretty good trip to do with kids. If you’re not up for it, wait a few years and then bring them or leave them at home. Either way, it’s a must-visit place at some point.