Five Reasons Off Season is the Best Time to Visit Aspen

“There is no such thing as off-season anymore,” said Kyle, a longtime Aspen local who has been working at the liquor store counter at Carl’s Pharmacy for the better part of the last decade. He shook his head and rolled his eyes.

It was a particularly busy Saturday on October 10, which historically would be considered off-season. But to look outside, at all the hustle bustle and the unseasonably warm, sunny skies, you would have thought it was still the middle of summer. It just goes to show: You never know what October will bring. Fall can be an amazing time of year with mild weather, beautiful foliage, and a dusting of snow on the high peaks. But one thing you can count on in Fall are better deals on airfare, lodging, and food with no summer crowds to have to share it with. Aspen regains it’s small town feel in the off-season, a quieter time when the true essence of the town reveals itself.

Aspen Tree Grove


Even though locals like Kyle would rather we not tell you this, here are five reasons off-season is the best time to visit Aspen.

#1) No one can predict the weather, especially not in Colorado.
There’s an old saying, “If you don’t like the weather in Colorado, wait five minutes.” That’s especially true in the Fall, when sunny, warm days can give way to blistering cold nights and the occasional snowstorm. But this year, we’ve been blessed with an endless summer. That means flip-flops and sundresses are still in rotation and there’s extra time for that hike or bike ride you’ve been meaning to get to, not to mention lazy afternoons lingering over cocktails by the pool and dining al fresco are still in season. Walking around town, you’d think it was still mid-summer but without the crowds and a much lower cost.

#2) You can always find a parking space.
This might not sound like a big deal, but if you’ve tried to navigate downtown Aspen in the summertime, you can appreciate what a luxury it is to be able to avoid driving in circles for 15 minutes before parking so far away from where you’re going that it would have made more sense to walk or take the bus. Fewer people means Aspen retains the small town feel that makes it special, the kind of resort that doesn’t require parking in an enormous underground garage and then jumping on a shuttle (like another ski resort we know where “a highway runs through it.”). This is also true for getting a table at your favorite restaurant or a drink in a less crowded bar.

#3) Bargains can be found, even in Aspen.
Let’s face it: Aspen is not a place often associated with discount shopping. But in October, when retail stores are making one last ditch effort to clear out old inventory, there are sales galore with deep discounts. Our favorite is the rack of designer denim at Boogies with markdowns as low as 75 percent off, not to mention the great finds that can be found in the shoe deparment, where popular brands like Frye, Steve Madden and Donald J Pliner can be found at great prices. This is also a great time to stock up on ski and snowboard equipment and clothing, when you can get brand new gear for half the price. Deals can also be found at some Aspen’s most popular restaurants (the real local’s favorites stay open through the off season) where pre-fixe dinners and other food and drink specials make dinner out, well…almost affordable. Finally, airfare into Aspen also dips this time of year, and flights are more readily available.

#4) The party never stops, especially on Halloween.

Lit Carved Jack-o'-Lanterns

After the wall-to-wall events calendar that goes non-stop all summer long, it’s nice to take a breather but still enjoy some special events in October, which tend to me more intimate and locally attended. The Aspen Art Museum remains open with exhibits running all month and admission is free to the public (still hard to believe, but there is really no excuse not go and check it out). The Harvest Party fundraising event for the Aspen Center for Environmental Studiesis the go-to event for the season. And The Belly Up continues to offer live music all month long, with noteworthy bands performing at our favorite music venue in downtown Aspen. Last but not least, Halloween is huge in Aspen and costumes are taken very seriously—with over 80 bars and restaurants in the downtown core, it’s got to be one of the best adult renditions of “trick or treat” anywhere in the country.

#5) … and neither does the beauty.
Cyclists, hikers, fishermen and lovers of the outdoors rejoice for the warm, sunny days that have prevailed in past years the whole month of October. The leaves seem to be hanging on a little longer, too, providing that extra sparkle for scenery that is already exquisitely breathtaking. And there are plenty of ways to experience our Aspen fall foliage, including enjoying a drive over Independence Pass.

Get started planning your “off-season” Aspen vacation. Click here to see our incredible inventory of luxury Aspen rentals.