The Definitive Family-Friendly Guide To Aspen, No Matter The Season

ASPEN — When I took my two children, ages 18 months and three and a half, to Aspen for a week in warm weather, I saw the town, which I’d visited numerous times before, through completely new eyes. My big realization? The town is one big family-friendly playground. There is so much to do, even if your kids aren’t old enough to ski or hike yet, for everyone to have age-appropriate fun. Here’s where to stay, eat, and play in Aspen year-round — without the younger family members feeling like they are being dragged along on an adult vacation, and without the adults feeling like they are being pulled into kiddie land.

Where to Stay

Sky Residences at W Aspen
The splashiest new hotel and residences in 30 years is also home to some of the best and most attentive service in Aspen. The Sky Residences — six three-bedroom and five two-bedroom suites — are located slope-side on Aspen Mountain and are ideal for families. The spacious layout includes a washer and dryer, e.g., the holy grail for anyone traveling with kids. The hotel’s rooftop is the hottest party in Aspen. At first, I thought my kids would be unwelcome interlopers to the scene (there’s usually a DJ spinning tunes in the afternoon and evening), but everyone was completely welcoming. And mine weren’t the only toddlers in the hot tub. (Start ‘em young, right?) The residences also have their own roof deck and hot tub. With rates that start at $1,199 per night in low season (April-May and October-November) and $1,499 in high season, the Sky Residences are a pricey option, but I thought they were totally worth the money. (The rates for the hotel start at $299 in low season, $699 in summer, and $799 in winter.)

Hotel Jerome, Auberge Resorts Collection
While the hotel’s buzzing bar scene ensures it remains one of Aspen’s hot spots, Hotel Jerome is also incredibly family oriented, with spacious adjoining rooms and new three-bedroom residences with private elevators and full kitchens, clocking in at a generous 2,000 square feet. The heated pool and two hot tubs are great for both relaxing and playing. The upscale, Western-chic vibe made me feel like a grown-up again. And that, as any parent knows, is priceless.

Limelight Aspen
The city's friendliest hotel (as in, single-friendly, business-friendly, family-friendly, pet-friendly) has just completed a terrific top-to-bottom makeover. All rooms and suites come with a huge television, microwave, Smeg fridge, humidifier (a nice touch). They have cribs and diaper genies if you need them, along with rollaway beds for $25/night — although any guest under four feet tall would be much happier in the teepee setup (sleeping gear and lantern) they can arrange for the same price.

Aspen Meadows
Why stay on the campus of the Aspen Institute? For the more accessible price point (two-bedroom suites in August start around $800/night). For the Bauhaus-inspired look and the gorgeous grounds. For options like two-bedroom suites with lots of room. And for the friendly service. The hotel is about a mile away from the center of downtown, but a shuttle makes getting around easy.

Aspen Street Lodge
Those looking for luxury and privacy should head to Aspen Street Lodge, which is great for family, extended family, and groups. The lodge is configured to have ten or eleven rooms, along with two theatre rooms, a game room, and two bunk rooms. In other words, enough space to be together and also apart.

Where to Play

When It’s Chilly

Ski and Snowboard School
Both Snowmass and Buttermilk mountains offer individual and group ski lessons for kids from age two-and-half. (Again, start ‘em young! As some say, if you can walk, you can ski.) Half- and full-day programs are available, as is the Aspen Highlands Kids & Teens Sunday program for ages 7 to 14 between December and March. Each week focuses on a new theme around skill-building on the mountain, such as edging, mountain safety, bumps, racing, freestyle, and more.

Anytime

Head to the Hills
It’s nice up at to the top of Aspen Mountain! And the gondola is easily the most scenic way to get there. Younger kids will like the treehouse and sandbox in warmer months. (They kept mine occupied for close to an hour, an eternity for toddlers.) Then settle in for lunch at the Sundeck — hot chocolate for them, hot toddies for you, pizza and soup for everyone. If you're not skiing, you can buy the foot pass up and just enjoy the view

Or make your way down along 75 ski trails, or explore on foot guided by Aspen Center for Environmental Studies (ACES). Those past the sandbox age can learn about wildlife, mining, and wildflowers on the free Aspen mountain walk in the summer months and a snowshoe tour in the winter.

For more kid offerings, head to Snowmass and take Gondola up to Elk Camp Meadows for zip lines, a high ropes course, disc golf, and downhill and cross-country mountain biking.

Ashcroft Ghost Town and Pine Creek Cookhouse
ACES leads another great tour to Ashcroft, a former mining town that now looks like a ghost town. This is a great half day trip to pair with lunch at Pine Creek Cookhouse, which is highly regarded for its alpine cuisine. Along the easy 1.8 mile walk to Pine Creek Cookhouse, you’ll learn about the history of Ashcroft, the wildlife species, and environmental stewardship, while enjoying absolutely phenomenal scenery. In the winter, you can only access to the restaurant via cross country ski, snowshoe, or by riding in a horse-pulled sleigh — no cars allowed.

When It’s Warm

Ebiking
I was a bit skeptical about ebikes until I rode one nine miles to and from Woody Creek and became a convert. Everyone could use a little help going uphill at altitude. And if you are attaching a kid trailer to transport your small humans, a little electric power isn’t such a bad thing. A company called Bike Butlers will deliver the bike directly to your hotel. (In the winter, they are the Ski Butlers who will come outfit your whole family with the ski gear of your choice, sparing you from having to shlep your equipment from home.)

The Aspen Music Festival
Students at the Aspen Music School show off their skills every summer in several daily performances all over town. We were lucky enough to catch the last performance of the season on the sprawling campus of the Aspen Institute. Find a patch of grass (so many to choose from), set up your blanket, lay out the snacks, and listen to Tchaikovsky while gazing up at the trees. The best part? Lawn seating is free!

Maroon Bells Hiking
For great summer hiking, reserve a shuttle (reservations are required) that leaves from Aspen Highlands and head to the Maroon Bells, the most photographed mountains in North America. For older children, the rocky, but beautiful, Crater Lake hike is challenging but highly rewarding. Easier hikes for younger children include the one-mile, round-trip Maroon Lake Scenic Trail and the 3.2-mile one-way Maroon Creek Trail.

Paddle Boarding
Normally I wouldn’t think paddle boarding was a good toddler activity, but it was one of the most fun mornings my three-and-half-year-old daughter and I had together. We were taken out by a wonderful guide through Aspen Adventure Company. The outdoor outfitter provides transportation, paddle boards, and attentive guides who paddle alongside you. I paddled (on my knees) through the North Star nature preserve while my daughter sat on the front scouting for wildlife. We stopped at “beaches” along the way — little sandy alcoves along the river. The beginner experience lasts about an hour, and options are available for more experienced paddle boarders.

Summer Camp
Camp Aspen Snowmass runs from June through August for kids as young as three. Activities include downhill biking, fishing, rocket building, and arts and crafts. Parents can sign up by the week, but should do it early because the camp is very popular and fills up fast. Another great option right in Aspen is the Gan Israel camp for children. Run through Aspen’s Chabad at their $18 million Jewish Community Center, it has many great facilities for kids, including a large, airy classroom and a playground.

Where to Eat

Woody Creek Tavern
The dining institution right off the Rio Grande River, now under new ownership, is the perfect reward after the 45-minute bike ride along the Rio Grande Trail from Aspen (or, if you're recovering from Saturday night, the ten-minute drive). Their elevated brunch will please even the pickiest of eaters. The salads and grilled cheese are standouts, and the corn bread should be a controlled substance. No need to take my word for it: The two-hour wait times for tables are a pretty big hint.

Prospect
Just like Hotel Jerome, its fantastic al fresco and indoor dining experience lets adults feel like adults and kids like kids — without anyone cramping anyone else’s style. There are crayons, highchairs, and an entire kids’ menu, as well as baked oysters, great cocktails, and the best cheesecake I’ve ever had. In sum, a perfect evening.

Ajax Tavern
The sundeck at Ajax Tavern at the base of Aspen Mountain is a reliable crowd pleaser for good reason. It’s a great family-friendly dining option with universally beloved and mouth-watering dishes like roast chicken, wagyu beef Bolognese, truffle fries, trout, and chocolate peanut butter pie, a bone fide next-level dessert. When it’s warm, sit mountainside and let the kids can run around on the grass. During ski season, come for lunch and catch the rays (it’s called “the sundeck” for a reason). You won’t leave hungry, and a meal here, even for a family, won’t break the bank. (Though, to be clear. “won’t break the bank” in Aspen can hardly be considered “inexpensive.”)

Parents’ Night Out

Bosq
The only chef-owned restaurant in Aspen is, perhaps not surprisingly, also one of the most inventive. Barclay Dodge forages for ingredients that result in a forest-inspired tasting menu of four, five, or seven courses, with dishes like smoked salmon crackers with black chili, summer pea, and flowers; lobster grilled over juniper branches; and beef tenderloin with wild watercress, hazelnut miso, and local porcini mushrooms. His may be the most sophisticated flavor palate in town.

Cache Cache
One of the most successful restaurants in Aspen has been a mainstay for 30 years, and it’s not hard to see why. The scene is fun and lively, the food is fantastic, and they serve the best martini I’ve ever had. For a parents’ night, we ordered escargot and king crab.

Casa D’Angelo
This new Florida-imported addition to the Aspen dining scene is the town’s new go-to for a sophisticated, elegant Italian dinner. While we saw a family with very well-behaved children eating here, we left our kids at home and did not regret the decision. A standout for food, ambience, and service, Casa D’Angelo hit high notes on the menu with charred octopus, Aspen salad, homemade maccheroni with vodka sauce, branzino, and a chocolate bomb made with a Nutella-like sauce with hazelnuts that the chef grows himself.

Sushi Nakazawa
Another mini chain to land in Aspen this year took over the space of Grey Lady, another East Cost import. The omakase at the open-air sushi counter is a terrific splurge — a decadent, delicious, and inventive multi-course meal (I lost count) that includes wagyu beef, king crab, and some of the freshest, most memorable sushi you’ll ever eat.

Not enough for you? Okay, okay. We have more restaurants, bars, hotels, shops, and art. Here's what's new in Aspen this season.