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Why Aspen became Hollywood’s favorite winter hideaway

October 1, 2026 By itravelnet.com

Aspen Colorado

Every December, no, no… literally every of them. This one, not a joke. So, a small former silver mining town in the Colorado Rockies starts collecting more famous faces per square mile than most red carpets.

Most of Private jets crowd the local airport. Plenty of guests land in Denver and rely on a car service to Aspen to cover the last 200 miles of mountain highway. The pull goes back more than 80 years.

How Hollywood Found the Slopes

Aspen’s early ski investors figured out that a few famous skiers could sell a resort better than any brochure. It worked:

•       In 1941, investors invited film star Jack Oakie for a weeklong ski vacation.

•       Oakie loved the trip and promised to come back with more Hollywood friends.

•       Gary Cooper later stayed for long stretches and became the town’s original celebrity regular.

•       Swiss racer Fred Iselin came from Sun Valley to run the ski school and brought famous friends along.

The Stars Who Stayed

Some visitors never really left. Aspen has collected part-time residents who could fill a studio casting sheet:

•       Jack Nicholson bought a West End home in 1980.

•       Goldie Hawn and Kurt Russell have owned homes here since the 1980s.

•       Snowmass named a ski lift and run after former resident John Denver.

•       Kevin Costner started building an Independence Pass ranch in the early 1990s.

Hunter S. Thompson lived nearby too and ran for Pitkin County sheriff in 1970, so the town was never only about fur coats.

A Calendar Built for Cameras

The yearly schedule looks like this:

Event

Timing

Why It Draws a Crowd

Holiday season

Late December

Peak weeks for star sightings downtown and on Aspen Mountain

X Games Aspen

Late January

Hosted at Buttermilk every winter since 2002

Aspen Shortsfest

April

Oscar-qualifying short film festival run by Aspen Film

Aspen Filmfest

Fall

Feature film showcase running since 1979

Why Stars Keep Coming Back

Locals usually point to a few reasons:

•       Famous people can walk down the street without drawing a crowd.

•       A billionaire in worn-out ski pants barely gets a second look.

•       Four ski mountains sit within easy reach of downtown.

•       The Hotel Jerome bar has hosted stars since the days of John Wayne and Gary Cooper.

The Drive From Denver

The scenic shortcut is off the table in winter, since Independence Pass closes for the season from roughly November until Memorial Day. The winter route is simple:

•       Take I-70 west from Denver to Glenwood Springs.

•       Follow Highway 82 south through Carbondale and Basalt.

•       Plan on about 3.5 hours in clear conditions.

•       Leave early on Fridays, when ski traffic stacks up near the Eisenhower Tunnel.

Once in town, everyone plays by the same rules, and even an Oscar winner is just another helmet in the lift line.

Filed Under: Travel Blog Tagged With: aspen, colorado, usa

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