Weather 
Two kids, boys about 10 years old, walk past the bar to the hostess stand of a popular restaurant in Aspen, Colo. “We’d like a table for two,” one says. The waitress doesn’t blink; she leads them to a booth.
The mountain town of Aspen isn’t just a gnarly spot of X Games sports, or a seventh home location for the world’s most rapaciously successful accumulators of capital (the median price of a single-family home hovers around $13 million). It’s also become a playground for . . . children. Very rich children, yes, but that isn’t their fault.
The pretty, pedestrian-friendly downtown, girt by gingerbread houses, is just five blocks across from Main Street to the gondola up Ajax (officially Aspen Mountain), and only about three times as wide. Cafes swell with families around Wagner Park Playground in the heart of the town’s pedestrian mall. Its curvaceous, wooden climbing structures were completed last fall, inspired by the city’s namesake trembling tree. But practically every inch of this at times ostentatious little town, once known for countercultural figures like Hunter S. Thompson, is kid heaven.
Strollers are like supercars, and sometimes made by the same brands. Bigger kids can roam freely (armed with dad’s credit card) in this supremely safe and privileged space.
Scooter-friendly streets, ice cream and shaved ice stands, a diverse restaurant scene and a bijou movie theater add to pre-adolescent interest. Best of all, a concentration of luxurt hotels — like Little Nell, Hotel Jerome, St. Regis and the newly opened White Elephant pamper juveniles with all-seasons programming and concierge services that are special to the 8,000-foot elevation.
“Aspen is truly a year-round escape that’s perfect for family adventure,” said Whytney Rawls, the travel adviser founder of the Amara Escapes. “Whether you’re an adventurer, a grand resort connoisseur, or looking for that Western feel we all dream of when visiting the spectacular Colorado Rockies, there’s something for everyone. [But] when planning an Aspen trip, thinking you can just show up and handle everything once you arrive is not the move, especially during peak winter dates.”
Here’s what top travel pros recommend for your family on your next (or first) trip to the town one adviser called “St. Barts with fur.”
Where to stay
Where you book will reflect what your kids are into. “For families with confident skiers who want the full Aspen experience, the Little Nell is the benchmark,” said Sangeeta Sadarangani, founder of Crossing Travel. “[It’s] the only ski-in/ski-out hotel on Aspen Mountain, with an excellent ski concierge and the town just outside the door.”
But a stay there is never cheap, and its sister property, Limelight Hotel Aspen, is a good, upbeat, less formal alternative.
Sadarangani sends families with younger children to Viceroy Snowmass. With ski-in/ski-out access, multi-bedroom residences and proximity to family-friendly terrain, it removes the fuss from the morning rush to the mountain. But know that Ajax, the mountain afront Little Nell, is serious stuff, with no beginner terrain.
For multigenerational trips, or for older teenagers looking to make the scene, historic Hotel Jerome, Auberge Collection, is the spot.
Although it’s in the center of Main Street, the hotel organizes a mountain of on- and off-season fun: from horseback rides through the Rockies, pony rides and horse-drawn carriages to family ski days, with ski fittings and private instructors on the beginner friendly slopes of Buttermilk or Snowmass — and après-ski for kids, including a build-your-own snowman kit.
In winter, ride a snowcat to the Lynn Britt Cabin restaurant for a Colorado-themed gourmet dinner.
What to do
Aspen is on a downhill, which is a good thing since most families come here to ski. But since the pandemic, it’s become a year-round destination that any guide will tell you is best enjoyed in the less-crowded summer.
Once you’ve checked in, have your family hit the trails. Bike scenic tot-friendly trails include the Rio Grande along the Roaring Fork River. Almost every hotel offers cruiser bikes, but rented e-bikes are how the cognoscenti get around.
Viceroy Snowmass
Sadarangani recommends the 0.7-mile Snowmass Village Nature Trail for younger children, or the area’s most iconic trip: the one-mile Maroon Bells scenic trail. “The Grottos [a half-mile loop trail near Aspen] is another family favorite, because children can explore the rocks and waterfalls,” she added. “I would then allow half a day for Lost Forest [a mid-mountain adventure park on Snowmass Mountain], where younger children have Robin’s Nest, the trout pond and climbing wall, while those tall enough can ride the Breathtaker Alpine Coaster.”
For children around 9 to 12, the Sierra Club Loop at Snowmass and Smuggler Mountain Overlook are great climbs, and adventurous children will want to attempt the Treeline Challenge Course, with its ziplines, bridges and rappels.
Teenagers will appreciate the challenge of Crater Lake or Hunter Creek, both half-day hikes. Or consider the 5.6 miles to Cathedral Lake (elevation gain 1,986 feet), or the 6.5 mile out-and-back to American Lake (elevation gain 2,034 feet).
White water rafting the Class 3 rapids in the Colorado River is another bonding experience (book with Blazing Adventures). Or teach the kids to fly fish with Aspen Outfitting Company located in the St. Regis.
Snowmass Bike Park is another teenage hang, but book a professional clinic, say experts. They’ll start in the learning area and on the green Verde Trail before moving up.
Indoor kids will appreciate the Anderson Ranch Arts Center, a workshop and creative space for children and teenagers interested in ceramics, painting, photography or digital art.
However, just loitering around America’s richest little town may be the best together time money can buy.
