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.

I started my career as a line cook at Hotel Jerome over 20 years ago, and I’ve been lucky to be executive chef here since 2012. Through the years, I’ve seen Aspen undergo a number of changes, but one thing has stayed remarkably constant: the Aspen Saturday Market, a community gathering spot since it opened in 1998.

To the rest of the country, Hunter S. Thompson might be best known as the godfather of gonzo journalism. Thompson lived and wrote on the edge in a style epitomized in “Fear and Loathing in Las Vegas,” which first came out in two installments in Rolling Stone before being published as a book that would end up defining the post-'60s counterculture. But to Aspenites, and especially here at Hotel Jerome, he’s best remembered for his 1970 run for sheriff of Aspen Pitkin County.

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.”

Next time you’re ordering your favorite cocktail at the J-Bar, ask about “the drawer.” And, after that, ask if your bartender has signed it yet. Famously known for its hundreds of intricately carved signatures, the drawer holds the names of every bartender who has worked in the J-Bar since its opening day in 1889. If you happen to be at the J-Bar at the right time, you might even catch a touring group from the Aspen Historical Society showing it off. Now shellacked to seal it’s inked history, the drawer is an Aspen landmark worth toasting to.