Aspen City Guide


So now that I’ve told you what to pack for Aspen (read the post here), I’m so excited to share what my top things to do, see, eat, and drink are in the fairytale town! I had some favorite spots I wanted to revisit from last year and definitely added some new ones to my list this trip.

If you missed my previous post, this was my second trip with the Tremblay Clan to Aspen, Colorado. The manfriend’s family has been making the hike to the Midwest for nearly 20 years so they all know the lay of the land pretty well and are all awesome skiers. I, on the other hand, have only been skiing three times in my life and I don’t think the time when I was 6 years old on the east coast really counts so I consider myself a novice skier (although I did get pretty good at the Blues on the “baby mountain” by the end of this year’s trip!) Luckily, there is plenty to do in Aspen if you’re not a skier, or are a new skier like me and want to take some time off between hitting the slopes. Shop my look below and read on for my guide to this magical winter escape! 


Sweater | Rose Wholesale

Leather Pants | Rose Wholesale


  • Mountain Chalet: the manfriend’s family has been staying at this quaint, family-run hotel for decades and it’s seriously the best deal in Aspen. Located downtown, it’s not very fancy, but puts you right in the center of the shops and restaurants, offers complimentary breakfast every morning, and always has fresh-baked cookies in the lobby. Not to mention, it’s one of the most affordable lodges in the town
  • LimeLight Hotel: if you’re attending Gay Ski Week, this is where you want to stay. The hotel is the event’s main headquarters and throws multiple parties throughout the week, complete with open bars and drag queens
  • The St. Regis: centered directly behind the Mountain Chalet, you probably saw this red brick hotel in a lot of my photos for the trip. The St. Regis is stunning and has an awesome bar and amnesties but is probably the least affordable option for lodging 


There are four mountains in Aspen, Snowmass, Highlands, Buttermilk, and Aspen Mountain, each offering their own unique terrains and restaurants. I’ve only ever been skiing on Buttermilk because I’m a beginner, but I’ve learned a lot about each of them over the years!

  • Buttermilk – this mountain is known as one of the best mountains in the countries for beginners to learn how to ski and while I may be biased, I agree. The mountain boasts the most greens out of the four, but has plenty of blues and blacks for those of you who want a challenge. If you take a lunch break on the slopes, opt for the Mongolian Grill at The Cliff House
  • Snowmass – the furtherest away from downtown Aspen, this mountain actually has an entire ski in, ski out resort on it. It’s the most family-friendly mountain and offers slopes for every level of skier 
  • Highlands – I could be wrong, but I’m pretty sure this is the favorite mountain of serious skiers. Fun fact – the local high school has a chair lift from the school’s property straight up to the mountain so its students can hit the slopes after class 
  • Aspen Mountain – commonly called AJAX, this mountain is smack in the middle of town and where the annual Gay Ski Week race takes place. Even if you don’t ski it, the 25 minute gondola ride to the top is worth the views. They also offer sunrise yoga classes on top of the mountain! 


  •  Brunelleschi’s – this restaurant has hands down some of the best pizza I’ve ever had. If you’re into thin crust pizza with tangy tomato sauce – this is your haven. The atmosphere is laid back, the food is fairly affordable compared to some of the white table cloth spots, and the service is great 
  • White House Tavern – if you’re a sandwich lover, this is where you want to go. The space is super tiny (it’s a converted home) but their piled high sandwiches pack a big punch. They also have a decent salad selection and excellent fries
  • HOPS Culture – I struggled whether to put this under eat or drink so know that it’s a great spot for both! From mac n’ cheese to taco salads and wings, this is gastropub fare at its finest. Wash it down with a brew from what can only be considered “a bible of craft beer” – they seriously have every type you could want 


  • Justice Snows -we loved this cocktail bar so much we went back twice! The drinks are pricey, around $16 a cocktail, but the mixologists are amazing and these were seriously some of the best drinks I’ve ever had
  • AJAX Tavern – nestled at the bottom of Aspen Mountain, this is my favorite spot for Aprés Ski because you can watch everyone come down the mountain while you sip your drink of choice on their heated patio. This is also the best place to watch the gay ski week drag race, but get there early because seats fill up fast! 
  • Aspen Brewing Company – walk into Aspen’s only brewery and you can instantly tell that this is where all of the locals hang out. The beer is good, dogs are allowed, and it’s fairly priced – what’s not to love?
  • Escobar – I’m throwing this in here due to its insane interior because there was no one there when we were there (apparently it gets the “late night crowd”) but this underground bar is definitely worth a visit. Completely Pablo Escobar themed, the bar mimics an airplane and has all sorts of crazy neon signs and lounge areas 


  • Aspen Art Museum – I fell in love with this museum before I even set foot in it because its facade is beautiful. The museum is smaller inside than you would think (you can get through the whole thing in under 45 minutes) but the exhibits are modern and innovative and they have great guidebooks for each installation. Top off your trip with a glass of prosecco at their rooftop cafe
  • Smuggler Mountain – the manfriend told me we were going for a walk around town and ended up making me hike up a mountain. you can imagine how thrilled I was about that. In all seriousness, the hike was beautiful but make sure you are wearing the right shoes (I was wearing my massive snow boots that give me blisters after 20 minutes) and bring water (we had none) because the altitude makes you dehydrated very quickly. Needless to say I bitched the whole way up because of these circumstances but if I’d been prepared it would have been a very lovely hike
  • Belly Up – one of my favorite nights of the trip was going to see Fruition at this amazing music venue. The concert hall has hosted everyone from Calvin Harris to Nappy Roots and has an intimacy that equates to the 9:30 club. Highly recommend catching a show here — even if you aren’t familiar with the band it will still be a blast! 

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