In case you didn’t know, media megastar Oprah Winfrey has long-been a homeowner in the Telluride area. Her first visit to this mountain enclave took place in 1992, far before the town’s most recent tourism boom and the international hype the destination receives today.

In a recent post made by Oprah on social media, she looked back at that first visit, remembering how one of the well-known hikes in the area left her gasping for air.

During that first visit, Oprah says she was at her highest weight ever – 237 pounds. Amid a lack of physical fitness and having traveled in from a lower elevation, she opted to tackle Bear Creek Trail – still one of the most popular hikes in the area today.

Rated 4.8 stars on AllTrails, this route is rated as a ‘moderate’ hike and it’s not exactly easy. It stretches 4.5 miles round-trip as an out-and-back trail with the main feature being a stunning waterfall at the turnaround point. The real kicker, however, is that it gains about 1,092 feet of elevation, with all of that gain coming in the first 2.75 miles during an uphill climb to the falls.

Oprah recounted that the hike took her half a day during her 1992 trip to the town, feeling “impossible” along the way.

“I never even looked up and saw the view because I was only focused on one foot in front of the other and trying to breathe in the nearly 10,000 foot altitude,” Oprah wrote of the experience.

More than 30 years later, on September 6 of 2025, Oprah returned to give the trail another shot. She happily reported to her social media followers that this more recent hike was quite different.

“Today, I finished the trail in one hour and 48 minutes,” she wrote. “I enjoyed every step, took in the beauty, and made it to the waterfall with my goddaughter Kirby, her husband Virgil, and hairdresser friend Nicole. Triumph!”

Now at 71 years old, Oprah’s pair of experiences on the trail shows how adopting a healthier lifestyle can have major impacts when it comes to enjoying the outdoor recreation space. One might assume an Oprah in her late-30s might be hiking faster, but that wasn’t the case. It’s never too late to make a change that can lead to a happier and healthier life. The example of Oprah’s experiences on Bear Creek Trail capture this reality in a motivating way.