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Road Trip to Aspen, Colorado

Road Trip to Aspen, Colorado

At nine in the morning, I get a phone call from my boyfriend to tell me to pack a bag. By noon we had the car packed and were headed on an impromptu road trip to Colorado! This was a pleasant surprise for the New Year’s Eve weekend. During the 12 hour drive towards Denver, we debated where in Colorado we wanted to go. We agreed upon Aspen because neither of us had ever been there before and it sounded like a magical place to ring in the New Year!  

With nothing planned in advance, I started researching on the drive. We found out that the time between Christmas and New Year’s Eve is Aspen’s busiest time of year. Most everything was booked in town but we lucked out and found a great Airbnb in Carbondale, about 25 minutes away from downtown Aspen.

First Stop: We used the Hotel’s Tonight app to find our $99 boutique hotel in downtown Denver, The Curtis Hotel. We stayed there on our way to Aspen to break up the drive.

In the morning we fueled up with a delicious breakfast sandwich from Masterpiece Delicatessen before we went to REI to grab some ski gear. Across the street from REI is an outdoor resale shop, Wilderness Exchange Unlimited, that had some great deals name brand gear.

Tip: Before heading West towards the mountains check on google maps to see if there is any traffic on HWY 70. Since there was a wreck on 70 when we left we took the scenic route through Fairplay.

If you stop in Vail on your way West go to Westside Cafe and Market for a famous bloody mary and take home one of their iconic coffee mugs. If you are in the area for dinner, eat at Mountain Standard in the Vail Village. Westside Cafe  for a famous bloody mary and take home one of their iconic coffee mugs. If you are in the area for dinner, eat at Mountain Standard in the quaint Vail Village.


Driving into Aspen the mountains get higher and more rocky than what is in Vail or Breckenridge. The Maroon Bells are two 14er peaks in the Elk Mountains. These peaks are some of colorado’s most photographed and you can access the iconic view from Maroon Creek Road right as you enter town. 

If you can afford it you can conveniently fly your private jet into the airport right at the base of the Mountain, which is full of jets from around the world. This airport’s convenience paired with Aspen’s seclusion is why it has become a vacation spot for the rich and famous. Aspen has changed over the years to adapt to the new infiltration of wealthy snow bunnies. Local mom and pop shops have turned into Prada and Dolce and Gabbana’s. Even Tesla has opened it’s first year-round resort town location here.

Roll into town and gather your bearings at the St. Regis Hotel bar. People gather by the roaring fireplaces in the dark, swanky lobby with walls of windows that face up at the mountain. Drink some wine and eat the free bar snacks while you make your plan of attack for the slopes tomorrow.

Slope Breakdown

1. Buttermilk is great for beginners but has blacks as well. It has the closest parking to the mountain and parking is free.

2. Highlands would have the second most greens but also has the double black Highland Bowl for expert skiers.

3. Snowmass is a huge mountain with lots of different terrain for all types of skiers. You will have to pay to park in the garage or you can take the shuttle. Parking is $20.

4. Aspen Mountain has no greens, is narrow and very challenging and the skiers are aggressive.

Learn more about each mountain here. Download the Aspen Snowmass mobile app to learn everything you need to know about your adventures on the mountains. 


Snacks on Buttermilk Mountain

Other Winter Activities

Uphill hiking
Take a fat bike for a ride
Ice Skating
Hot Air Balloon Rides


Aprés Ski

The world class Aprés Ski is the best part of going to Aspen! After a day of skiing check these places out to get a drink and admire all the stunningly beautiful people that vacation there.

39 Degrees at Sky Hotel
Cloud 9 on Aspen Highland Mountain
Ajax Tavern at the Little Nell Hotel


We found that there is no shortage of dark, sexy bars where you can sip bubbly. A few of our favorites were…

Hotel Jerome’s Living Room Lobby Bar
Crêperie du Village
St. Regis Hotel Bar
Justice Snow’s

Food Scene

The food scene in town is off the charts. At least in Yelp reviews it is! It had the most 4.5 star ratings I’ve ever seen. So you will not be disappointed with almost anywhere you go. The most recommend spots we heard about were

Meat & Cheese Restaurant and Farm Shop
Crêperie du Village
New York Pizza
White House Tavern
Grey Lady Aspen
Cache Cache



You have to stop by the Penny Hot Springs in the Crystal River near Snowmass. It’s free and you can park your car right beside the river and it’s just a short walk down to the spring. It was pretty crowded the day we were there and the locals said it’s usually more crowded. But we met the most interesting people and it was well worth it! 

Enjoy the snow! 

Penny Hot Springs, Snowmass, Colorado 

Follow my Aspen Pinterest Board for more travel ideas!

 Photography Journal



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