A Winnowed Guide to the Best Aspen Days

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Empty house lots in Aspen don’t sell for $22 million just because of good skiing and Kantian vistas. The sublime summer climate and vast cultural offerings elevate Aspen from scenic town to a promised land for independent travelers. Here’s a winnowed guide to the best of days.

Winnow is here to help you uncover your own best, version of Aspen. There’s more tucked into this little valley than meets the eye and with help from our network of local insiders, you can seamlessly find, book (and pay for) the best of the best. And, there’s a way to connect generations of mountain knowledge with the convenience of modern technology.

So let’s get started.

Arrival Day:  “Easy Does It”

Unless you are visiting from the Himalayas, the effects of Aspen’s nearly 8,000-foot altitude will no doubt tax your energy. In addition to lots of H20 to hedge the lack of O2, we recommend some easy-does-it activities. First off, stroll or bike the Rio Grande trail or the East Aspen Trail, both of which start right in town and have gently sloped, paved trails that meander through forests and along the river. (Aspen WeCycle bikes are free for the first 30 minutes.) 

Stretch, re-calibrate and expand the lungs with a Enjoy a wellness morning for a mid-vacation reboot$1400 for 6 guests2 Hoursprivate yoga session (either at your home, at the studio, or Perfect your asanas with mountain-top yoga$250 per guest2 Hourson top of Aspen Mountain) with one of Aspen’s most popular and beloved yoga teachers.

For something less taxing, try a little Design your own cowboy hat in a vintage saloon$580 per guest1 Hour 30 Minutes mad-hatting, cowboy style at the new and improved Kemo Sabe. Not only does a visit to this old-school Aspen shop jumpstart your Western fantasia, your new hat will come in handy for the rest of the trip (P.S. there’s a secret saloon upstairs that will really ignite the Old West “spirits.”).


Day 2: “Over the River and to the Bar”

The Marble Distilling Company in CarbondaleSee experience

Rocky Mountains Rivers are a spiritual experience. Of course, Fish the Roaring Fork River in perfect silence$375 for 2 guests4 Hoursfishing is a popular activity and a particularly magical experience for couples as long as you don't compete too hard for the most fish. For a little more adrenaline for the whole family, there is no shortage of Tick river rafting off your bucket list with a custom adventure$680 for 10 guests5 Hourswhite water rafting

A float of any kind means you have to take out somewhere down valley and whilst there, we highly recommend a stop in Carbondale. Nicknamed the Brooklyn of Aspen, Carbondale’s kooky village vibes are a nice counterpoint to upscale Downtown Aspen and it’s also where you will find the Marble Distilling Company. Using the fresh mountain water you just floated, Savor Aspen-made spirits on a private distillery tour$30 per guest1 Hourgo behind the barrels to on a private tour of their distilling floor before heading out front to sample the finished product.

Kids Alright? Book Aspen Nannies to watch over the little ones. They offer Let your little monsters loose with cookie decorating$50 per guest1 Hourcookie and cupcake decorating as a wholesome distraction.


Day 3: “For the Soul: Culture, Shopping & Spas”

As Hugh Grant once said, “Love, actually, is all around,” and in Aspen that love, actually takes many forms; in the vistas, the music, the art, yes, even the shopping. However you like to connect with something greater, or just with yourself, here are some ways to do it:

For the ears: The Aspen Music Festival and School offers hundreds of concerts at myriad venues. For example, Perfect your asanas with mountain-top yoga$250 per guest2 Hoursfloat up Aspen Mountain on the gondola for a morning yoga session, either take a group class or Sharpen your shoulder stand with private yoga instruction$138 per guest1 Hourbook a private session. Jaws will drop at the view and then again after lunch as Juilliard students site-read Bartók off their iPads. What we especially enjoy are the Master Classes where you can see the musicians work their craft, because even the best musicians in the world make mistakes sometimes.

For the eyes: There is so much art in this little town, so hand over to our Tour Aspen’s galleries with an art insider$325 for 4 guests2 Hourslocal art enthusiast guide who will take you around to only the best galleries and shows. It make for a very relaxing way to get your bearings and focus on the best art in town.  If you are curious about the artistic heritage or Aspen, Get to know the Aspen Institute Collection on a private tour$145 for 10 guests1 Hourbook a tour of the incredible campus and art collection at the Aspen Institute. This is perhaps the most intact and pristine example of Bauhaus art and architecture in the world.


Day 4: “Great things happen when man and mountain meet.”  - William Blake

Regardless of gender, if some proper mountain adventure is what you seek, Aspen has it in spades. Iconic hikes include the Maroon Bells, Cathedral Lake and American Lake. We also have guides that will take you on Hike up to the picturesque mountain town of Crested Butte$295 per guest11 Hoursthe magical journey to Crested Butte or Hike to the top of a 14,000-foot mountain$595 per guest6:00up one of Colorado’s “14er’s.” There are 54 peaks in total that rise above 14,000 feet and we believe that there truly is no greater thrill than climbing them. And when you’re back in town, have an Pamper yourself with a private in-home massage for the ultimate unwind$225 per guest1 Hour 30 Minutesin-home massage, Bliss out together with a massage for two$450 for 2 guests1 Hour 30 Minutescouples massage, Sharpen your shoulder stand with private yoga instruction$138 per guest1 Hourin-home yoga, or Explore the potential of Chinese medicinal healing$200 per guest1 Hour 30 MinutesChinese Healing therapy booked and ready to go.

Browse online or download the Winnow App. Take a second to set up your profile. A few taps on the screen, and you’re tapped into the very best Aspen.

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