Wheeler Opera House
320 E. Hyman Ave., Aspen
The redbrick-fronted Wheeler Opera House is an icon in Aspen. It’s been around since 1889 and was the first building in Aspen to earn a spot on the National Register of Historic Places. Today, it’s an all-purpose entertainment center and hosts a full series of events, like film and comedy festivals, magic shows, and every kind of musical act you can think of.
Highlands is known for having some of the most challenging terrain in Aspen, offering steep runs and, of course, the legendary Highlands Bowl. It's not a huge mountain, but it's absolutely the place you want to be on a powder day. (Though you'll be fighting locals for the first chair if that's the case.)
The original resort here, Aspen Mountain is the closest of the mountains to the village, with its lower runs spitting out skiers at the doors of the Little Nell. The mountain is known to locals as Ajax, and it's a favorite among them for its convenient location and its steep, bumpy style.
The least steep of the four mountains, Buttermilk is typically a favorite of beginner skiers (whether they're little kids or adults who are just getting the hang of things). In the spring, the mountain's entire personality completely changes when the X Games hosts its competition there for the week. If you happen to be in town, have your concierge arrange for you to see a few of the events in person.
Hike Cathedral Lake
Though they're iconic in many ways, the Maroon Bells can get grossly crowded. For those who prefer to enjoy the mountains in quiet silence, Cathedral Lake offers plenty of views and requires a lot less sharing. Meanwhile, the picturesque lake at the top makes a photo-worthy picnic spot and a perfectly serene place for a few casts. Fair warning: At 7 miles round trip and steep in some areas, this hike isn't for the faint of heart. Leave early to avoid getting caught in afternoon thunderstorms, which are are all but guaranteed in the summer. Photos: Protrails
601 E. Dean St., Aspen
Aspen's Roaring Fork Valley is home to four different rivers, and between them they make up some of the best fly fishing in the United States: In the summer, the cold mountain waters are home to gorgeous rainbows, brown trout, and more. Even inexperienced fishermen will appreciate the scenic surroundings; most finishing spots also offer panoramic views. While guide companies are a dime a dozen, Aspen Fly Fishing is our pick—their experienced guides will tailor a trip to your needs, whether that means fitting you with waders or organizing a full-fledged float trip.
Aspen Center for Environmental Studies
Hallam Lake, 100 Puppy Smith St., Aspen
The Aspen Center for Environmental Studies (ACES), which operates out of four different locations in the area, is a tremendous community asset. The organization provides classes and a host of educational activities for the community from a nature camp for kids, to senior birdwatching, to cooking classes using local ingredients, and everything in between. Visitors can hire a naturalist guide from the center to give a personalized—and vastly informative—tour of the surrounding mountains, focusing on wildlife, native plants, and more. You'll go by foot in the summer and snow shoe or cross-country skis in the winter.
The Maroon Bells
Maroon Creek Rd., Highlands, Aspen
Even if you've never been to the Maroon Bells, there's a good chance you've seen them before—the view of them from the parking lot is one of the most widely photographed vistas in the United States. While driving up the trailhead (there's a $10 entrance fee) is gorgeous, it's also crowded. To find some quiet, head up in the winter when you'll have to snowshoe or cross country ski to reach the view, or hike up to nearby Crater Lake via a 3.6-mile trail—it's steep, but worth it for the constant photo-ops.
315 E. Hyman Ave., Aspen
Cycling is a pretty huge part of Aspen's culture, especially in the summer, when the professionals make their way through town in the Colorado Pro Cycling challenge. And while some of the most famous rides are best left to the experienced or the extremely fit (the climb over Independence Pass, for example, is challenging), there are plenty of options for beginners as well. Bike Hub of Aspen will outfit the entire family with bikes and send you out with maps and information about where to go. As a warm-up, check out the paved Rio Grande bike path that spans much of the Roaring Fork valley, which is as tame as it is stunning.
555 E. Durant Ave., Aspen
Glenwood Springs (which you'll drive through on your way to Aspen if you fly into Denver) is a cozy little laid-back town, and it's home to sections of the Colorado River that are anything but. In the summer, kayaking and rafting trips through the stunning Glenwood Canyon are not to be missed. Blazing Adventures can set up an outing for any level of experience, from beginner-friendly kayaking to heart-pounding raft trips over difficult stretches of rapids. They also do SUP rental.