Let’s break it down, why travel to Aspen? Ski Vacation? Celebrity Stalking? R&R? Take it from a local, you can do all of that and more. Keep reading for a locals perspective and how to conquer this little mountain town with a big reputation.

An Ultimate Local’s Guide to Aspen, Colorado

Aspen, Colorado: that idyllic mountain town nestled at the base of Aspen Mountain, known as Ajax to the locals. It is a town of only about four square blocks of weathered and rustic brick walkways and historic buildings from the 1800’s, many modernized and updated for the mountain bougie touch.  As you stroll along you will pass fountains and streams, parks and flowers, as well as high end retail like Gucci, Prada and Ralph Lauren.  There are also five star hotels, crafty breweries, high end eateries, coffee shops, private clubs and music venues. However for locals, the town is not defined by upscale retail or the wealthy tourists who flock here. What the Aspen locals know and why most of them are here is that this area is one of the most stunning mountain regions in the world. Nature at it’s finest. Majestic mountain ranges made up of several 14ers (14,000 foot peaks), glimmering Aspen trees, rushing streams and lakes, world class skiing, bluebird skies and an average of 246 days of sunshine per year make it an idillic setting for people who want to get outside for hiking, biking, skiing, walking, rafting, golfing, climbing and SUP…you get the idea!

Tourists have quickly discovered what the locals would like to keep secret. This is a town surrounded by nature, a mountain town, that has amenities that you would find in many vibrant cities. Here in Aspen one’s lifestyle choices can and do change by the day. One can live a life filled with outdoor pursuits one minute, like skiing and hiking, and then trade in your ski boots for heels and a night maneuvering across the cobblestones searching for the perfect Espresso Martini.  Or maybe that’s just me?!  From Bull Run to the Belly Up, Lost Man to Las Montanas, the choices and variety is what makes this town so desirable.  This Ultimate Local’s Guide to Aspen will answer your questions whether it’s your first time or whether you are a repeat offender. And whether you roll budget or bougie – we gotcha!!

When to Visit? There is a Reason for that Season

We have a saying that people come for the winter’s but stay for the summers. Many locals started out as ski bums just trying out the snow and the town for a season. Then the snow melts and Aspen turns into a different type of wonderland. Aspen is an old mining town that sits at 8,000 ft, a mountain town, a ski town that fills up (it’s packed!) in the Winter with avid snow sports enthusiasts from around the world. The Winter customer skis hard and plays harder.  We have seen a change though and now Aspen’s Summer has become just as crowded. The town transforms, the snow melts and the Aspen trees and grass turn green, the weather is perfect with warm temps during the day and temps a bit cooler at night, the mountains suddenly become hikeable, the ice and snow melt and rivers and streams start flowing. There are many events scheduled to lure and keep visitors entertained, starting with the official kick off to summer: Aspen’s Food and Wine Festival. F&W is followed closely by: the Aspen Ideas Festival, Aspen Music Festival, July 4th parade, AAM Art Crush, JAS Aspen Labor Day Concert, Snowmass Thursday Concerts on the hill etc- there is always so much to do during the summer and Summer tourism has eclipsed Winter. 

If you are like me and want to explore a new destination without the crowds, there are the shoulder seasons to consider – Spring and Fall. 

Let’s break down the seasons with a guide for what each season offers – Winter, Spring, Summer and Fall.

Then we will go over where to sleep, where to eat, what to wear, and how to have fun!!