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It’s no secret that Aspen, once a sleepy mountain town, is home to a swanky winter wonderland. Before the snow bunnies descend, consider a fall trip when crowds thin, days are blessed with sunshine, valleys are stocked with wildflowers and the town’s namesake trees spawn a brilliant golden-yellow. With nature at her finest coupled with high-adrenaline Rocky Mountain activities, elevated culinary ambitions, and cultural offerings, we've put together an insider's guide on what to do, where to eat, and where to rest your head.

Hiking the Rocky Mountains

Alas, you’ve come to Aspen (altitude: 8,000 feet) to breathe in the fresh air. For those who want to expand their lung capacity—and bragging rights—enlist in hiking a “14’er,” the state’s collection of peaks towering over 14,000 feet. Wait a few days to acclimate, and then call Aspen Alpine Guides to organize your climb. Don’t forget a sturdy pair of Keen boots, moisture-wicking layers from Fjallraven, and ample hydration (mixed with either Acli-Mate or chlorophyll drops). For more moderate hikes, consider Smuggler Mountain Trail or opt for Hunter Creek or Sunnyside Trail. Want to pedal? Cyclists enlist on the steep climb to Maroon Bells—largely void of cars, while the relatively flat Rio Grand Trail offers some downhill relief. For horseback riding, spend a half-day on the uber-scenic Maroon Creek ride with views that rival a ‘70s Marlboro Man commercial. You can also take in the sights from the comfort of your car; the scenic ride to Ashcroft Ghost Town is punctuated by sweeping views and Aspen groves.

Books, Art, Music, and Western Ware

In the mornings, stroll the Saturday farmers market stocked with locally-grown produce and baked goods. On Galena Street, the venerable western storefront Kemo Sabe stocks belts, cowboy boots, and their own hat label—which they’ll mold with high-powered steam based on how you like it to rest on your head. Nearby, get lost in the boho-flared, book-lined gem Explore, followed by caffeinated brew at Local Coffee, which also hawks chic souvenirs. Music buffs drop by iconic venue Belly Up (whose hosted Kenny Rogers and The Flaming Lips, respectively) or visit Wheeler Opera House for comedy and film billings. For visual delights, Shigeru Ban’s Aspen Art Museum, a modern, wood lattice cube is a striking place to view art followed by lunch at SO rooftop café. History fans enjoy the small Aspen Historical Society followed by a visit to Aspen Institute; who recently installed artist Hebert Bayer’s Anaconda sculpture and next year, will celebrate the 100th anniversary of the Bauhaus School. Finally, it’s legal to buy marijuana in Colorado, so pop by Silverpeak Cannabis; a handsome, wood-infused dispensary with “budtenders” who educate on the latest edibles, pre-rolls, and pens.

Diverse Dining and Drinking

For the most creative food in town, nab a table at Bosq where native chef Barclay Dodge’s elevated cuisine (Peking duck, crispy eggplant) employs ingredients from local farms. Meanwhile, Element 47 serves refined French-American food and houses an epic wine collection (call ahead and see if you can sneak down to their famed red-hued cellar touting a rarified ‘85 Romanee-Conti). For breakfast, Poppycocks Café (est. 1971) serves famed oatmeal buttermilk pancakes while the local’s lunch favorite Grateful Deli is stocked with subs and paninis. The health-minded Pyramid Bistro serves grain bowls while Meat & Cheese doubles as a spot for house-smoked meats and artisanal cheese. For seafood, the timber-chic Clark’s Oyster Bar has you covered. And for burgers and beers, don’t miss the legendary J Bar, which once doubled as Hunter S. Thompson’s campaign office and watering hole. Speaking of drinks, Jimmy’s Bodega pours a well-curated list of tequila and mezcal. For cocktails with a view, drop by Plato’s.

Where To Rest Your Head

Backing up to Ajax Mountain, the recently-updated The Little Nell is an exercise in contemporary art and pet-friendly wonder. Its 92-rooms are dressed in a creamy palate with pops of blue and gray. What’s more; the service is some of the nicest in town. Fall excursions include off-road tours and hooking rainbows on custom fly fishing trips (request the amicable Brady) to either Roaring Fork Valley or T-Lazy 7 Ranch’s stocked ponds. Afterward, sip mountainside pints at Ajax Tavern.

A few blocks away, the 93-room Western-Victorian infused Hotel Jerome is dressed in elevated western style—leather writing desks, burnished bedframes, and new spacious suites (with kitchens, fireplaces, and balconies). The property also hosts guided 14’er adventures. Feeling the effects of altitude? Sign up for the High Altitude Sports Recovery Massage (ask for Christopher) and add-on the CBD-infused deep salve to cure what ails. For late night cocktails, sneak down to the new dimly-lit subterranean bar, Bad Harriet.

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