Updated Aspen, Colorado Travel Guide 2021

OTTEstyle Aspen Guide

I’ve grown up going to Aspen with my family and it holds a special place in my heart. It has been so fun to have so many memories there and it is easily one of my favorite places in the entire world. I was so excited to share it with Sam when we were dating and I hoped he would grow to love it in the same way that I always have… and he definitely does. So to say that we are both anxious to share it with Nora and start creating memories there with her would be an understatement.

This is an update on a blog post I wrote about Aspen a few years ago- my recs are all the same but I added some fresh links with a few things I’m packing for our trip!


OTTEstyle Aspen Guide






OTTEstyle Aspen Guide: Skiing

We usually opt to stay in a house when we travel with my entire family so we can spread out and have our own rooms, but also have a space to hangout together and watch movies or play games at night. If y’all have a large family (consisting mostly of adults) and this is something you’re interested in, I suggest checking out Home Away. I think it makes a trip feel so different when you’re staying in a residence, almost like you’re a local! But, for a quick weekend getaway or a trip with your guy– a hotel is also a really fun option for Aspen.

  1. The St. Regis Aspen Resort: right in the heart of downtown Aspen, upscale-lodge feel
  2. The Little Nell: ski-in/ski-out access to Aspen Mountain, F A N T A S T I C location and views of downtown
  3. The Viceroy Snowmass: ski-in/ski-out access to Snowmass Mountain, 15 minutes from downtown Aspen, more “family-friendly” vibes but still a luxury hotel *best of both worlds*, also have to add because its me, duh, its pet friendly πŸ˜‰
  4. The Ritz Carlton Club of Aspen Highlands: ski-in/ski-out access to Aspen Highlands, condos available (game changer!!)
  5. Hotel Jerome: super cool, historic, an Aspen “must see”


OTTEstyle Aspen Guide: Skiing
OTTEstyle Aspen Guide: Skiing

So there are four mountains to ski in Aspen: Buttermilk, Snowmass, Aspen Highlands and Aspen Mountain. Now I am *by no means* an expert skier, I like to say I can get down just about anything but I can’t promise it’ll be pretty! Sam, on the other hand, is just about as good as it gets and we both can enjoy ourselves on these mountains.

Buttermilk is much more “beginner friendly” and also where ski school is located (if you’re showing up in Aspen with no experience, I definitely suggest checking this out for a few days). My family skis with the same instructor (hi, Bryna) every year because 1. she’s our friend and 2. we can always benefit from a few pointers PLUS she knows all of the mountains like the back of her hand and knows what we are all capable of skiing. Any who, Buttermilk has lots of great greens to learn on or just spend the day warming up.

Snowmass is the largest of the four mountains, I believe I heard once that all three of the other mountains combined are still not as large as Snowmass. SO that means theres lots of options and something for anyone at any level to ski. I’m ALL ABOUT a groomed run and Snowmass has a lot of great blues and blacks for the intermediate skier who is trying to perfect her S moves (aka me). PLUS there are tons of fun and delicious restaurants and shops at Snowmass Village (the bottom of the mountain) for lunch– y’all know I’m a fan of atmosphere.

Aspen Highlands is a little more tricky but definitely doable for intermediate skiers. This is Sam’s favorite of the four mountains because it has a lot of steep black diamonds– my nightmare. If you’re feeling on top of your game, you can even hike up the bowl and ski down some double blacks… no thanks! I’ll leave that one up to you, SD– I’ll be waiting at the bottom, hot cocoa in hand!

Aspen Mountain is the fourth mountain and (in my P E R S O N A L (aka unprofessional) opinion) the trickiest to ski but also totally doable for intermediate skiers. My favorite part about this mountain is the views, it looks right over downtown Aspen. Your girl definitely gets a little side tracked when skiing this mountain because… pictures. If you’re not into skiing, you can always ride the gondola up Ajax and have lunch at the top of the mountain and just ride the gondola back down, how nice does that sound?


Aspen cuisine is my favorite cuisine. There are SO many delicious places to eat and I suggest trying them all– so essentially just eat your way through Aspen, alright? But if you’re on a schedule and need to just hit the high points, here are some I suggest:

  1. Matsuhisa: same owner/head chef as Nobu // sushi + sashimi + small plates
  2. Kenichi: apologies that the first two are sushi, but– priorities. I read on an Aspen blog once that “if you can’t get into Matsuisa, try Kenichi…” so, yeah I agree. // sushi + small plates
  3. Steakhouse 316: prohibition vibes // GREAT steaks + tons of sides
  4. La CrΓͺperie du Village: such a cool underground space, a M U S T for dessert // nutella crepe with bananas and strawberries
  5. Woody Creek Tavern: a local spot, very casual, “pool hall” vibes // ribs + burritos (yeah, what a mix)
  6. Bosq: great for cocktails
  7. White House Tavern: small little miners cottage, no reservations // sandwiches + fries


OTTEstyle Aspen Guide: Shopping

Downtown is FULL of shops, from North Face to Moncler– there is literally something for everyone. Besides the brands that y’all know (Rag & Bone, Burberry, J.Crew… etc.), there are tons of local gems! My personal favorites are Pitkin County Dry Goods for regular clothes and Performance Ski for ski attire.

There are also several outdoor activities, besides skiing! We’ve gone snowmobiling to the Maroon Bells before and it was such a FUN experience with the most gorgeous views. I’ve always wanted to go night tubing, but we’ve never been able to make it happen– its on my to do list though. Has anyone tried it before?