I’ve always been drawn to Aspen for its artsy side. Hunter S. Thompson lived in the area for 40 years. John Denver lived there and wrote Annie’s Song in his head while riding up Aspen Mountain on a chairlift. Jimmy Buffet made it his Key West-West for a spell, and Stevie Nicks wrote “Landslide” while staying in Aspen. While you still see some archeological traces of Freak Power, Aspen is more about luxury these days. I was about to drive into the heart of it.
Day 1: The Road To Aspen
We hopped off a plane from Charleston and were handed the keys to a 2026 Lexus LX 700h Overtrail—the luxury automaker’s ultimate SUV in its most rugged offroad-ready trim. Though even the offroad model, which starts at around $117k, has all the creature comforts you could want, like massaging seats for long rides and a refrigerated console for keeping beverages frosty.
We passed through the highest city in North America at 10,154 feet, Leadville, then turned right towards Independence Pass; a summer-only roadway closed from October to May, but which offers an incredible—if harrowing—drive. Cute towns, hairpin turns, cliffs without guardrails as you ascend, and then finally a wind down towards Aspen, where the road narrows to one lane in places that are marked only as “do not pass.” In the home stretch it follows the Roaring Fork River and takes a sharp turn at a towering rock face that had a half-dozen belay ropes attached to climbers working their way up.
Queen Of The Silver Boom
Our destination was the Hotel Jerome, part of the Auberge Collection. Built in 1889 during a silver mining boom, Aspen’s original luxury hotel is still the city’s best. Valets in cowboy hats usher you into an entryway the feels like a step back in time, with fireplaces crackling, stag mounts and Old West relics on the walls.
My wife and I split a Wagyu burger on arrival at the J Bar, at a booth beneath Hunter S. Thompson memorabilia, then settled into a gorgeous room overlooking the street and Aspen Mountain, which was bright orange and yellow with autumn.
Our first foray into town was a stop at Kemo Sabe, a high-end Western outfitter specializing in customized cowboy hats. As soon as you walk in, you’re paired up with an enthusiastic salesperson, you pick out your base hat from the hundreds hanging on the walls, and then in a flurry they’re adding an assortment of bling—branded initials, ribbons, leather bands, semi-precious stones, pins. During this process, an $800 beaver hat can turn into an $1,800 beaver hat pretty quick. The upstairs VIP bar keeps the gears greased and the yesses coming, and soon you’re standing out front telling yourself you’re a cowboy hat guy now. But when in Aspen…
Dinner our first night was at Bosq, where the kitchen of Michelin-starred local chef Barclay Dodge, who spent time working at El Bulli, blew our minds with dishes that resembled miniature Zen gardens on the forest floor and tasted like Nirvana.
Day 2: Fly Fishing & Fixing Chakras
“Pressure” is the word that fishing guides use to describe fish that are constantly caught and released and get wise to the trickery of man. In other words, keep your ego in check in these waters. That’s because the Roaring Fork River is public, and it flows through the center of Aspen. I took it as a challenge. Christopher, our guide, was ex-Air Force with the handsome angularity of Fast Time at Ridgemont High‘s Jeff Spicoli. After fishing with guides all around the country, I find them to be remarkably similar, as if the job naturally selects for certain personalities to such an extreme degree that they all seem like a brother or a cousin of the first fishing guide you ever met.
Christopher was intense and stayed on me like a middle school math teacher, responding to my every botched set with an “Ahh, that was a fish.” Nevertheless, I managed to land five nice trout before peeling off my waders in triumph. Knowing of course that if the rod had been in his hands, the number would’ve been tripled.
After a leisurely Italian lunch at Casa Tua, we headed to massages at Yarrow Spa at the Hotel Jerome. Writers are all shameless gossips when it comes to getting under the hood of any subculture they parachute into, so I picked the brain of my massage therapist about the local off-the-record pulse. My takeaway was that while winter is prime time for Aspen, summer and fall are the seasons favored more by the locals. Though I’d love to experience both, I felt lucky to get in before the winter crowds.
That night we had dinner at the excellent Prospect at Hotel Jerome, followed by drinks at The Living Room, a cozy, dark, and moody lounge and cocktail bar that you’d want to lose hours in on a winter night.
Day 3: Climbing Aspen Mountain
We woke up to a welcome change of plans: After a rainy night, our planned hike was swapped for a chance to take the SUVs on an off-road drive up Aspen Mountain. I’d been staring out at the grassy would-be ski slopes from the window of our room the whole time and leapt at the chance to conquer the mountain on wheels. We drove up to a parking area for contractor vehicles coming and going on their off-season projects, then onto a muddy single-lane road that people would soon be skiing down to avoid a black diamond.
This is where I really got to feel the offroad DNA of the Lexus. Separate from the on-road drive modes like Eco, Comfort, and Sport, the LX has several offroad drive modes like Dirt, Sand, Mud, and Deep Snow. We put the LX into 4Lo on the Mud drive mode for the final push to the top of the mountain, then left it in 4Lo and manual for the descent to let the engine be our brakes. As the LX rolled smoothly down the road gashed by construction vehicles, I realized that because of the smooth trip out from Denver, I had been thinking about the LX as a road vehicle that can go offroad. But once I actually got offroad, I could just as easily describe it as an offroad vehicle that can go on a freeway.
The Lexus LX first appeared in the U.S. in 1996 as the Land Cruiser’s luxe sibling. Now that the latter has gone through its dramatic redesign with a more rugged look, the Lexus LX is the new standard bearer for that full-size luxury off-road lineage.
That afternoon, we had a caviar tasting in the Garden Room at the Jerome. Petrossian on kettle chips, washed down with glasses of Dom Perignon, served by someone in cowboy boots and a Western shirt. In other words, a perfect encapsulation of the over-the-top mountain luxury that the Hotel Jerome is known for.
Our final dinner was at Matsuhisa; a meal I’d been looking forward to since we got to Aspen. Many years ago, I had my first serious sushi experience at Matsuhisa’s Los Angeles location. I was in my twenties and bartending at L.A.’s Chateau Marmont Hotel. One of my favorite regulars, a Swedish actor, took me to dinner there with his son, who was on the verge of fame himself. I’d never had such a genuine invitation to cross the bar, socially speaking, and I never forgot it. Fast forward many years, and getting to have Matsuhisa’s world-class sushi in Aspen with my wife was the perfect follow-up.
Day 4: Like A Dream
It was 4 a.m. and pitch dark when we set out on our return drive to Denver. The hotel lobby was so empty, in my imagination I could feel the silver boom spirits in the silence. This time we skipped Independence Pass, taking instead the more traveled route where there would be no cliffs without guardrails in the dark. But if you have to do a four-hour drive at 4 a.m., do it in a Lexus LX. The cushy cockpit made the drive fly by, and the massaging seats made up for a lack of caffeine that morning. As we pulled up at the departures door at the Denver airport and handed back the keys, it was barely 8 a.m. On the plane, I was asleep before the seatbelt sign went off, with our time in Aspen fading into a very good dream.
It’s been nearly six decades since Hunter S. Thompson coined the term “Freak Power” to rally the Aspen subculture around a common identity. A lot has changed since then, but when you get beyond small talk with the cool locals, you can still feel that pulse. Or, as Thompson once said about a different place from his past, “With the right kind of eyes, you can almost see the high-water mark—that place where the wave finally broke and rolled back.”
