Aspen: The Kind of Ski Trip You Just Love

We started the morning heading straight to Aspen Highlands, which is always one of our favorite mountains. The views are incredible, the runs are fun, and it’s one of those places where you keep saying “just one more run” and suddenly it’s the afternoon. For lunch, we stopped at Merry-Go-Round Restaurant right on the mountain, which is such an easy and fun spot to take a break, grab something warm, and sit out in the sun before heading back out.

After skiing, we made our way into town. Walking through downtown felt like a movie scene, with snowy streets, twinkling lights, and beautiful storefronts everywhere you look. We spent time popping in and out of boutiques, browsing everything from cozy winter wear to high-end shops, and just taking it all in. We made a stop at Aviator Nation, which is such a fun little shop known for its super soft, colorful sweats and relaxed vibe—the perfect place to pick up something cozy for the trip.

We grabbed a coffee and wandered over to Wagner Park, which sits right in the middle of town. It was so peaceful with the snow all around and the mountains in the background, and we took a little time to just sit, relax, and enjoy it.

That night, we headed to Ajax Tavern for dinner, which is always such a great spot after a full day. I recommend ordering the wagyu burger, truffle fries to share, and a cocktail or glass of wine. Make sure to book dinner ahead of time, especially during ski season—it gets busy, and this is one of those places you don’t want to miss.

We started the day skiing at Aspen Mountain, which is right in the center of town and so easy to access. The runs here are a little more advanced, but the views and overall experience make it completely worth it, especially being able to ski right down into town at the end of the day. We stopped for lunch on the mountain and had chili, which was exactly what you want on a cold ski day—something warm, easy, and so satisfying before heading back out for a few more runs.

If I had planned ahead, I would have made a reservation to take a snowcat up to Cloud Nine Alpine Bistro for dinner, which is such a fun and unique experience. But instead, we stayed in town and had dinner at French Alpine Bistro, and it ended up being the perfect cozy night.

We ordered cheese fondue to share, schnitzel for dinner, and a banana crêpe for dessert, and it was one of those meals that just felt so fun and relaxed. Sharing everything made it even better, and after a full day of skiing, it was exactly what we were in the mood for.

On our last full ski day, we headed back to Aspen Highlands. We spent the morning skiing and made our way to Merry-Go-Round Restaurant for lunch, which ended up being quite the party scene. Everyone was dressed up in costumes, music was playing, and people were dancing, it felt like a celebration right on the mountain.

After skiing down, the energy kept going at the base where there was another party with a live band and a DJ—such a fun and unexpected way to wrap up the day on the slopes. It’s one of those moments that just makes Aspen feel so unique and memorable.

That night, we kept things more casual and headed into town, ending up at Aspen Brewing Company, which was such a fun, easy spot after a full day. We ordered a beer flight to try a little of everything, along with a pretzel and some shareable bites, which was perfect for a relaxed night.

My tip would be to lean into the energy of the day—Aspen has this way of turning a normal ski day into something so much more, especially toward the end of the season.

After wrapping up our time in Aspen, we added one more day and made the drive out to Ouray, and this ended up being such a cool and unexpected part of the trip. Often called the “Switzerland of America,” it’s surrounded by dramatic mountain peaks that make you feel like you’re in a completely different place.

One of the most unique things here in the winter is the ice climbing. Watching climbers scale frozen waterfalls is incredible to see in person and something you don’t experience in many places. We also visited Box Cañon Falls Park & Nature Center, which was such a highlight. It’s a short, easy walk, and then suddenly you’re standing right in front of this powerful waterfall rushing through a narrow gorge. The sound and energy of it make it so memorable.

The town itself is small, charming, and very picturesque, with cozy streets, local shops, and even creative spots for glass blowing and pottery if you want something hands-on. We passed by Wright Opera House, which adds to the historic feel, and there’s also a well-known hot springs pool that would be such a great stop to relax if you have the time.

If you’re feeling adventurous, there are even more options like off-road tours, hiking, and exploring nearby ghost towns. It feels completely different from Aspen, and adding it on gave the trip such a unique and memorable ending.