Planning a trip to Aspen, Colorado: A travel guide from a family who calls Aspen home

Aspen, Colorado is no walk through the park, ranking as one of the most expensive vacation spots in the United States. This city is elite, attracting affluent families worldwide. For my family and I, Aspen has been our home for two decades, nestled in a cozy community on Snowmass Mountain. We embrace Aspen with a low-key profile, frequenting favorite restaurants, enjoying incredible skiing, stunning hikes, and cherished après-ski moments.

A trip to Aspen, Colorado calls for planning and this is your travel guide to do so!

This post is dedicated to my family, who have been there for each other through and through. 

1. Places of stay

2. Skiing

3. Where to ski

4. Buying a pass

5. Après-ski

6. Hiking & Other Activities 

7. Restaurants

8. Cafes a. The Holy Beloved - Paradise Bakery

9. Shopping

10. Bars
    

Places to stay

The city of Aspen within itself will offer exquisite and high-end hotels. If seeking something on the “cheaper” side, I would recommend searching for places in “Snowmass” which is about a 20-minute drive from downtown Aspen. This is where my family and I reside, being that Snowmass Mountain is hands down the best mountain to ski on during winter times. 

• Cheapest option: Aspen Chalet

• More expensive:

  •  If seeking to experience Aspen like a local and experience a week-long timeshare on Snowmass Mountain, please reach out to me HERE with your inquiries and dates.

  • Places on Snowmass Moutain 

• The most expensive: St. Regis, The Little Nell, Hotel Jerome, W Aspen

Skiing

a. Where to ski

1. Snowmass Mountain: Easily the best mountain to ski in Aspen. With 94 runs and around 21 chairlifts, it accompanies any and all levels with extreme fun and icon views. The Cique headwall is a highlight for me!

2. Highlands Mountain: A more overall steep mountain. Beyond stunning and features the iconic bowl and cloud9 which is known for its crazy champagne-spraying daytime parties

3. Aspen Mountain: Another overall steep mountain for a skier's paradise. You will find more skiers enjoying this mountain and more snowboarders enjoying Snowmass Moutain. Not much variety and open space like there is on Snowmass Mountain.

4. Buttermilk Mountain: Not a mountain I would recommend unless you are a beginner at skiing. Lessons can be held here to get down to the basics.

b. Where to buy a pass

• You can find information and pricing about tickets here. Your best bet is to obtain the ticket once at the mountain. 
  

c. Apres ski

• Ajax Tavern: At the bottom of Aspen Moutain, it’s always a fun time here.

• CHICA: Another spot at the bottom of Aspen Moutain, views and drinks are immaculate

• Sundeck on top of Aspen Moutain 

• Cloud Nine: Such an iconic spot but insanely expensive. Reservations are needed and only open during the winter time!

Hiking & Other Activities:

a. Hiking:

• Ute Trail: Easily the top-recommended hike with the most rewarding views of the city. Rather short but mostly steep!

• Maroon Bells: A must-visit if here during the summer! Buy tickets in advance!

• Smuggler: A 7-mile hike that is rarely fully completed unless seeking a FULL day hike! Can easily turn around whenever desired! 

• Rim Trail South: Make sure to stop at the Yin Yang platform or the hike will go on for miles. My favorite hike - quiet, relaxing, and not very low-demanding! Stop at the Yin Yang for a snack, stretch, and meditation. 
  

b. Other Activities:

• A1 Oriental - Foot Massage: After a few days of skiing or hiking, this is your spot. This place has turned into my family’s sanctuary as we come here religiously when in town. A1 masseuses with customizable massages - such a special treat. 

• Bike from Snowmass to Aspen: a favorite daytime activity - Best bike rentals here and can be dropped off in downtown Aspen afterward. 

• Downhill Mountain Biking: An exhilarating adventure during summer or fall time. 

• Whitewater Rafting: This company offers rafting as well as other fun summer activities, like paddle boarding down the river.

• Snowmass Rodeo: Grab your boots and cowgirl hat to experience the best Wild West Rodeo! Every Wednesday night from June 19- August 21, gates and BBQ at 5 pm, show starts at 7! 

Restaurants:

Sushi & Fine Dining:

• Matsuhisa: Top sushi restaurant in the city

• Madame Ushi: Sushi but with a party club scene 

• Jing: Asian-infused sushi

• Kenichi: Sushi house est. 1991

• Clark’s Oyster Bar: Fantastic oyster bar with a variety of seafood options

• Casa Tua: High end Italian 

• Catch Steak: The name speaks for itself!

• Monarch: A delicious high-end steak house

• CHICA: High-end Latin flavors 

Relaxed Dining:

• Meat & Cheese: A family beloved spot! Featuring mixed cuisine, our favorites are the chicken and the pork board. Also open for lunch, no reservations!

• White House Tavern: A comfortable Tavern within the city! The crispy dings sandwich and the French dip are our recommendations!

• French Alpine Bistro: My favorite spot! A cozy little bisto with fondue, crepes, gnocchis, and more!

• Mawa’s Kitchen: Michelin guide recommended flagship restaurant - Black and woman-owned, featuring organic and African-inspired flavors!

• Mi Chola: A casual Mexican spot.

• Little Ollie’s: Casual and relaxed dining vibes, featuring dim sum and other Chinese classics. 

Down and Dirty: 

• Woody Creek Tavern: Been in the city as long as we can remember, a down-and-dirty pub for some good grub.

• Aspen Hickory House: A classic BBQ house

• New York Pizza: late-night pizza 

Cafes:

• Spring Cafe: Vegan spot with a variety of pastries, salads, sandwiches, smoothies, and hearty bowls!

• Swedish Hill Cafe: Brand new from Austin, a great lunch spot in the Aspen Art Museum. 

• Jus Aspen & Jus Snowmass: Juice bar featuring hearty and healthy choices!

• Jour De Fête: Little French-inspired counter cafe.

• Sant Ambroeus: A delightful bakery & cafe from Milan. a. The Holy Beloved - Paradise Bakery:

  • The one and only! Not only freshly prepared baked goods and sandwiches made from scratch every morning, but serving the best ice cream since 1981! It doesn't get more Aspen than this spot!

Shopping: 

• Pitkin County Dry Goods: Selling the majority of the hippest, trendiest, and laid-back clothing, shoes, jewelry, and accessories in all of Aspen

• P E 101: A small shop on a corner home to my favorite Lauren Mochi sweatpants and sweatshirts, with other cozy and trendy apparel.

• Kemo Sabe: A western apparel store nationally known as the best spot to customize a cowgirl (or boy) hat and get a kick-ass pair of cowgirl boots!

• Chrome Hearts: Doesn't get better than this - a luxury brand from Hollywood creating unique and edgy jewelry, clothing, and accessories with a dope punk twist!

• Kith: Nuff said.

Bars:

• Escobar: DJ's & checkered dance floor - a trendy nighttime spot.

• The Sterling: Night club in downtown Aspen.

• The W Hotel Rooftop

• Silver City: Cocktails, wood decor, and live music.

• Belly up: A fun and hip music venue with special performances!

With these guides and tips, covering all the seasons, I guarantee the ultimate trip to Aspen, Colorado! Peace and love to the cutest little city!

Xoxo,

Chelsey