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With its upscale boutiques, haute restaurants, and A-list celebrity residents, Aspen has rightfully earned its reputation as a posh mountain hideaway.
But the biggest mistake you can make is to pigeonhole this town as all style and no substance. Founded in the 1880s as a silver mining camp, Aspen has always had a surprisingly genteel side: When other mining towns were concerning themselves with saloons and brothels, Aspen chose to celebrate its boom years by constructing elegantly colorful Victorian cottages and the stately 1889 Wheeler Opera House. The founders would be proud to know that the town still shows off its brainier side with its annual slate of cultural festivals, such as the Aspen Music Festival, the Food & Wine Classic, the Aspen Ideas Festival, and Aspen Filmfest.
The city's contemporary art museum has been such a rollicking success that it will be moving into brand new digs in 2014 — a sustainable cultural center with 12,500 feet of gallery space, a black box theater, and a public rooftop with uninterrupted views of Aspen Mountain. Though Aspen can be surprisingly bookish, that doesn't stop it from letting its hair down. In the warmer months, you'll find residents fly-fishing in some of the state's best trout streams or hiking and biking on trails through forests of the town's namesake tree. But Aspen, of course, really comes to life in the winter, when it seems like the entire town is out on the slopes. And with four adjacent peaks to choose from, you're sure to find one that suits you, whether you're looking for the family-friendly runs on Buttermilk Mountain, the record-breaking 4,406 vertical feet of Snowmass Mountain, the expert black-diamond terrain of Aspen Mountain, or the steep open backcountry of the Aspen Highlands.
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Summer brings massive crowds of anglers to area rivers, but local experts know that spring can be an amazingly fruitful fly-fishing season with a fraction of the competition. In the early spring, before massive snowmelt raises stream levels, the Fryingpan River tailwater near the Ruedi Reservoir is a great place to snag a rainbow or brown trout. In fact, Aspen's lakes and rivers are so teeming that they've been named Gold Medal waters by the Colorado Wildlife Commission, a designation given to only 170 of the state's 9,000 miles of streams and lakes. If you're new to the sport, you may want to consider a lesson with Aspen Outfitting Company — they're sure to know the area's best spots!
In Colorado, the best summer wildflower hikes are called "century" trails, because you'll see 100 or more varieties along the way. Just outside of Aspen in the Maroon Bells-Snowmass Wilderness, the hike to Crater Lake offers a stunning selection of flowers in every color imaginable — yellow aspen sunflower, blue columbine, scarlet paintbrush, pink wild rose. The trail blooms to life from late June through August and reaches its peak in the first half of July. Along the way, keep an eye out for yellow monkeyflower and bittercress: The leaves of these vitamin-rich plants were used like lettuce by the Native Americans and make for an extraordinarily hyperlocal trailside snack.
It's no wonder Aspen was named for Colorado's favorite tree, which bursts into gold each autumn: This area was made for leaf peepers. One of the best places to catch the foliage in this corner of Colorado is the Maroon Bells. About 10 miles southwest of downtown, these three purplish peaks are said to be the most photographed mountains in North America. The trees here are at their most vibrant during the month of September. Crowds are appropriately massive on weekends, but there's a quick shuttle bus from downtown, meaning you won't have to battle traffic jams to see the fall's great display.
For more than half a century, Buttermilk Mountain has been known as Aspen's go-to spot for beginner skiers, thanks to its gentle, hilly terrain. But the ski area isn't all just a walk in the park. In fact, it has a rather extreme side, too: Buttermilk is home to the Winter X Games at least through 2014. Frequently ranked the best snowboarding terrain park in the world, Buttermilk boasts a slope-style course with 40 jumps and 25 rails, plus a 22-foot superpipe where pros like Shaun White test out their latest gravity-defying stunts. If you're not quite up to Shaun's level when you arrive, sign up for a full-day snowboarding class to hone your skills.