With its lively buzz and Old West vibe, the legendary J-Bar isn’t just Aspen’s social hub. It’s also a reminder—and bustling relic—of the town’s rich history. Cowboys and miners once rode their horses through J-Bar’s doors during Aspen’s silver boom, and drinks are still slung over the original century-plus-year-old maple bar. When Prohibition struck in 1920, J-Bar went the way of a host of other bars across America: it became a soda fountain. “Necessity is the mother of invention,” as they say, and the Aspen Crud was soon born.

I moved to Aspen last summer and soon adopted the same ritual as a lot of locals I know: trekking up Smuggler Mountain for an invigorating morning hike. The usual reward is a sweeping view of the town of Aspen and the Roaring Fork Valley from the observation deck at the summit. But on my last trek, I found another reward far sooner. Just off the first turn, I spotted a wooden swing carved with the words #AspenSwingProject. Whether you use it for a short rest, or pump your legs for a childish thrill like I did, the swing truly is a “random act of kindness.”

My wife Maggie and I are Co-Captains of the Banquets Team, where you will usually find us presiding over wedding receptions and corporate events, orchestrating all the minute details from setting up 12-piece place settings to making sure the procession of courses and wine pairings goes smoothly. But I also lead a double life. As many mornings as possible, I soar like a bird high over Aspen as a paragliding instructor. It’s the most exhilarating feeling to see the four ski mountains—Aspen, Snowmass, Highlands, and Buttermilk—and the entire valley from such a high vantage point.

Hotel Jerome has a rich history, one that parallels with the history of Aspen itself. During its silver boom years in the late 19th century—when fortunes rose dramatically and all anyone could see was up—department store magnate Jerome B. Wheeler envisioned a rival to the grande dame hotels of Europe. Hotel Jerome was born.