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Credit: Toby Harriman

With Love, From Aspen

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Dec. 9 2022, Updated 2:37 p.m. ET

How To Explore Colorado’s Most Chic Winter Playground

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Credit: Toby Harriman

Celebrating its 75th anniversary as a ski resort this season, Colorado’s most famous winter playground, Aspen, has been a thriving mountain hamlet since the late 1800s. Founded in the 19th century as a rip-roaring silver mining town, Aspen’s original red brick architecture still forms the foundation of its walkable downtown today.

Located in a valley surrounded by jagged mountain peaks and groves of aspen trees in Colorado’s Roaring Fork Valley about 3.5 hours southwest of Denver, Aspen is a year-round outdoor adventure destination. But it is in winter that it really shines. The stomping ground of the rich and famous (it’s often hard not to bump into a celebrity here), it is known for its steep ski slopes, ritzy resorts, chic restaurants, designer shopping and wild nightlife.

Follow our guide for how to play in Colorado’s most chic winter playground.

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Where to Play

In winter the main attraction is skiing. And with four mountains to choose from within a 30-minute radius of each other there is plenty of terrain to explore. In town there is Aspen Mountain, often referred to as Ajax, which is the most famous of the four resorts owned by Aspen Ski Co. and also home to the steepest terrain. This is where to ride if you want to see and be seen and the apres ski scene here is like no other. Just note there are no green runs.

For more diverse terrain, including options for beginners, head to nearby Snowmass Mountain Resort (the same lift ticket works for all four Aspen area ski resorts), which also boasts Colorado’s longest run. The aptly named Long Shot covers 5.3-miles from top to bottom. Aspen Highlands and Buttermilk are the two other area resorts. Buttermilk is for true newbies and a good place to get into your flow, but not much fun once you know how to ride. Aspen Highlands is where everyone heads in the spring as its higher elevation keeps the snow fresher longer.

Where to Stay

The Limelight Aspen is our favorite place to sleep in town. Walking distance from the slopes, it offers less expensive and less stuffy lodging than some of the other resorts. Plus the four-star property just finished a top-to-bottom remodel in 2021. The 126 rooms and suites have a vibrant chalet chic ambiance that feels super comfy and relaxing.

The hotel is known for its top notch, complimentary breakfast that features all sorts of hot and cold staples that will fill you up for a day on the slopes. Other perks at the Limelight Aspen include a restaurant with a great happy hour, a scenic rooftop terrace area with plenty of seating and a swimming pool and hot tub.

If you want the creme de la creme, book The Little Nell. Aspen’s only five-star, five-diamond property, it sits right at the base of the mountain and attracts a host of celebrity guests. Another top luxury choice is the Hotel Jerome. Aspen’s oldest property first opened during the silver rush in 1889 and was designed to look like a grand European hotel. Today it has elegant mountain decor and lots of Wild West memorabilia in the public spaces.

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Where to Eat

If you aren’t staying at the Limelight (where the breakfast is free) then fuel up at Poppycock’s first thing in the morning. A local staple, it serves Aspen’s best breakfast all day. The giant breakfast burritos with homemade green chili are the way to go.

If you are riding you’ll likely eat lunch on the mountain (see ‘Where To Drink’ below cause Ajax Tavern is tops) but off piste check out Hops Culture. It cooks up gourmet pub grub including super tasty Nashville-style hot chicken sandwiches. White House Tavern is another good spot that many argue has the best burger in town.

Keep it simple at dinner and order the wood oven pizzas from The Lounge restaurant at the Hotel Limelight. They are affordable and delicious. Pair with a microbrew. The restaurant also serves a full menu of elevated pub grub come dinner — the Wagyu Bolognese is a filling favorite.

Other top dinner spots include an outpost of the famed Matsuhisa, which is one of just a few Nobu restaurants personally owned and run by Nobu Matsuhisa and his family. It does all its classic nikkei offerings including a mixed seafood ceviche and miso-glazed cod that is to die for. The French Alpine Bistro is a romantic favorite cooking up French fare in low-lit mountain chic environs.

Where to Drink

Right at the base of the Silver Queen Gondola, and part of the Little Nell hotel, Ajax Tavern is Aspen’s definitive lunch and apres ski spot. You’ll want to order a bottle of bubbly and a dozen oysters to start. Other stellar menu items include the Wagyu double cheeseburger and the truffle fries. There is seating inside and on the large outdoor patio facing the ski hill. For apres the party moves to the surrounding concrete and there are often DJs and pop-up events.

Cache Cache is a scene-y restaurant that also does great cocktails at its marble bar. It’s a great people watching spot that isn’t too loud. Eric’s Bar is another fun choice for a low-key night out. Here you can rent pool and shuffleboard tables by the quarter-hour.

Bad Harriet, a speakeasy bar at the Hotel Jerome, is another sexy apres spot. It has a secret pairing menu where you’ll get a tequila cocktail and a mini taco one day and whiskey and a bite-sized pastrami sandwich the next. Also at the hotel, J Bar heats up after dark. The 19th century bar is known for its vintage-inspired craft cocktails and Old West buzz.

Escobar is one of the hottest clubs in town. The sexy basement spot offers bottle service at private tables and the best DJs in town. Weekends are packed. Another popular dancing spot is Belly Up Aspen, which might be the most iconic club in town. It’s been around for decades and serves up live music on its small stage. The venue can only hold 450 people but attracts major talent and seeing a show here is a very intimate experience.

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