How To Ski, Eat & Party Your Way Through An Aspen Adventure

How To Ski, Eat & Party Your Way Through An Aspen Adventure
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As part of StyleCaster’s Second Annual Ultimate Ski Trip, the SC team has had the opportunity to see some of the most magical (and varied) terrain on the planet. From the untouched 360-degree views of Banff, Canada, to the international splendor of Verbier, Switzerland and the East Coast “peaks” of Stowe, the team at StyleCaster is ready to keep you up-to-date on the best cold weather winter destinations, gear and style so you can hit the slopes like a seasoned pro too.

Click through the slideshow above for our guide to Aspen. We’ve got it all — from where to ski to where to rest your head after a hard night of partying. (And trust us when we say we don’t believe in doing anything half way.)

For more information on booking your trip, head to!

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The view of Aspen from high atop Ajax Mountain.

Ajax Mountain

Right in the center of town Ajax (a.k.a. Aspen Mountain) is by far the most popular. An excellent mountain to see and be seen, the terrain is challenging, picturesque and easily navigable. Due to its excellent location, you’re likely to find slightly longer lift lines and more crowded slopes than the other mountains, but it is worth it.

Vitals: Base elevation is 7,945 ft. with a summit of 11,212 ft. There are 64 miles of runs on 76 trails covering 675 acres of terrain. With 8 lifts including a high-speed gondola that takes you from the base to the top in 14-minutes flat.

Aspen Highlands

Also known as “The Locals’ Mountain” Highlands has something for everyone. With 360-degree vistas of the surrounding landscape, a quaint base village and the legendary Highland Bowl, a visitor can want for nothing on this epic piste. (SC tip: Go with a guide or trusted local and hike the 12, 392 ft. vertical rise to the top of the Highland Bowl for the ultimate in inbounds-backcountry rush.)

Vitals: Base elevation is 8,040 ft. with a summit of 11,675, and the hike to the top of Highland Bowl at 12, 392 ft. There are 84 miles of runs on 118 trails covering 1,028 acres of terrain. With 5 lifts, 3 of which are high-speed quads.

Highland Bowl

One of the great experiences at Aspen Highland Mountain is the hike to the 12,392 foot summit. Not just for locals, this trek is well worth the effort, scoring all whom accomplish this physical feat access to the freshest powder and tree skiing in the area.

Photo: Jeremy Swanson

Just before entering the Highland Bowl after a long hike.


Coming in at 4,406 vertical feet, Snowmass has the most in the country. A truly massive mountain, one could spend their entire ski vacation here. Snowmass is located approximately 30 minutes via free shuttle bus from the center of Aspen town. A destination unto itself, Snowmass Village has restaurants, shopping, and a family-friendly environment that caters to any whim.


Base elevation is 8,104 ft. with a summit of 12,510. There are 147 miles of runs on 91 trails covering 3,132 acres of terrain. With 21 lifts including an eight-person gondola.

Photo: Jeremy Swanson

Sushi at Matsuhisa


Cuisine: Japanese and sushi

Diner’s Notes: You just cannot go wrong with “Matsu” as the locals call it. A slice of NYC or LA in the heart of the Rockies.

SC TIP: The bar scene is where to head on short notice. All the quality, half the fuss.

Recommended dishes: The unmistakable Yellowtail and jalapeño, and the Cod with Black Bean Sauce

Cloud Nine

Cuisine: Swiss/Austrian

Diner’s Notes: By far the pinnacle (or summit) of on-mountain dining. This Swiss-inspired chalet has limited seating so make a reservation in advance.

SC tip: Beyond the fondue, the name of the game is Raclette, order yours at least 24-hours in advance. Also, this is not a quick stop to refuel, expect to spend 2-3 hours at least. We hear the après-ski scene is pretty insane as well.

Recommended dishes: Fondue, Raccalette, any soup of the day.

The view from Cloud Nine Alpine Bistro.

The premiere restaurant in the Viceroy Snowmass. EightK (aptly titled for its elevation) serves up local fare and hearty Rocky Mountain flavors in a modern setting.

Casa Tua

Cuisine: Northern Italian

Diner’s notes: Situated in the alpine outpost of the famous Miami private club, Casa Tua is a true locals’ see-and-be-seen crowd. Try to snag a table downstairs unless you are with a member (the upstairs is exclusively members-only).

Recommended dishes: Casa Tua Tuna Tar Tar, Artichoke Carpaccio


Cuisine: Refined rustic

Diner’s Notes: Could this be Aspen’s best? The price-fixed menu leaves nothing out. Chef Robert McCormick has reinvented the menu when he took over in 2011. A semi-formal environment lends itself perfectly to a date-night or dinner with the parents.

Recommended dishes: Charcuterie plate (all meats are cured in-house), Liberty Farms Duck and the Venison Tenderloin

Woody Creek Tavern

Cuisine: Mexican with a twist

Diner’s Notes: One of Hunter S. Thompson’s mythic hangouts, Woody Creek is the equivalent of the Mos Eisley Cantina. It’s a spot where well-dressed ladies mix with gruff locals over strong margaritas, nachos and burritos. The food is simple and excellent. The art on the walls reminds you of a truly authentic T.G.I. Friday’s and every song on the jukebox is the perfect song for that moment.

SC tip: Slightly off the beaten path, take a taxi or drive there (about 20 minutes outside of town).

Recommended dishes: Nachos and margaritas, what more can you ask for?

Campo de Fiori

Cuisine: Italian

Diner’s Notes: One of Aspen’s sceniest spots, but don’t let that deter you. The people watching is fantastic and the food exquisite.

Recommended dishes: Tagliata (steak), Gnocchi Sorrentina

Caribou Club

The classic members-only club, there is always something happening at the Caribou. Find someone who can get you in and party until the wee hours.

Belly Up

THE place to see live music in town. This hot-spot attracts big talent you'll never see on a stage this small again.


Definitely the most talked about bar this season, Finbarr’s has tons of beers on tap, beautiful people and a great atmosphere.


The center of the Apres-ski scene in Aspen. Located at the base of the goldola, it arguably serves up the best burger and truffle fries in town. Snag a spot on the outside patio during a sunny day and watch the world go by.

Photo: Daniel Bayer

Private House Parties

There's always a ridiculous amount of house parties happening in Aspen. And as it happens, when we were there the good folks at Krug champagne sponsored a palatial home in the hills overlooking town. Keep your ear to the ground to find out where the scene is.

SC tip: Check our friends at for the latest goings on in town.

The Viceroy

As far as we're concerned there's only one place to stay at Snowmass Village; The Viceroy. Opened in 2009, the 173-room resort is the only one in Snowmass to boast ski in/ski out access with its own lift and slope to boot. Rooms are fashioned more like apartments in the mountains and are exquisitely appointed with fireplaces, kitchens, and Neil George products in the bathrooms. Upon check-in, make sure you call the ski valet to have your gear stored (and tuned if needed) to minimize losing any precious powder time. The Viceroy has two main restaurants, Nest for pan-Asian slope-side sushi and sake and Eight K -- one of the best restaurants in all of Aspen-Snowmass. We recommend visiting the spa for a restorative deep-tissue massage to sooth muscles after tearing up the mountain. (SC Tip: Arrive as early as you can to your treatment to take advantage of the quiet room).

No expense has been spared in slope-side luxury as seen in this one bedroom suite. Two LCD TVs and a freestanding fireplace are just a few of the amenities you can enjoy.

The pinnacle of relaxation. Make sure you arrive at the Viceroy’s spa early in order to take complete advantage of the relaxation room before your treatment.

The Gant

All of the comforts of home with all of the luxury that is Aspen, the Gant’s condo residences are run like a hotel. Located at the foot of Aspen Mountain, it's located just a few blocks from the Ajax lifts (no bother with their complimentary and on-call shuttle service). The resort boasts 140 condos, ranging from one to  four-bedrooms (our two-bedroom featured a balcony, complete modern kitchen, 2 bathrooms, fireplace, and 3 flat-screen TVs…but who’s counting?). The front-desk and concierge staff are all eager to please with any requests, and the outdoor pool is one of the largest and most relaxing we’ve ever encountered at a ski-town hotel. All guests also receive access to the Aspen Club and Spa’s fitness center on the off chance you need to work out any more after a day on the slopes. Oh and did we mention that airport transfers are complimentary?

The two-bedroom options at The Gant are the perfect size for a family or up to six friends. It features a modern kitchen, wood-burning fireplace, patio and flat-screen TV.

One of the better outdoor pools in a ski town we’ve encountered. The Gant’s pool also features an outdoor fireplace, two hot tubs and enormous swimming pool.

St. Regis

The 179-room St. Regis is perfectly located on Aspen’s Wagner Park at the base of Ajax Mountain just a stone’s throw from everything.  The Remede Spa could be Aspen’s finest and the treatments are out of this world. One of the more unique offerings that caught our attention was the onsite outpost for Aspen Outfitters who can plan excursions (skiing-based or not) to picturesque areas throughout the valley.

(SC Tip: arrive at 4:15 where the daily tradition of champagne sabering begins. First started by St. Regis founder John Jacob Astor, a sword is used to slice off the cork of a champagne bottle signifying the transition between day and night.)

The Sky Hotel

A little like entering Wonderland, the Sky has a great après ski scene and a youthful/chic vibe that appeals to 20-30 something professionals.

Little Nell

Hang your hat at the Little Nell hotel after a night of heavy snow. “The Nell” as the locals affectionately refer to it, is the ever-present grand-dame of Aspen. The Little Nell is situated right at the base of the Ajax lift. Head here for incredible dining, the après-scene, celebrity sighting and luxe shopping. Trust us, the Nell has it all.

Photo: Jason Dewey


One of Moncler’s three US stand-alone shops with items not available in department stores, pick up the perfect puffer, hat or jacket to make all of your friends at home jealous.


Born in Aspen and located at the base of Highlands, Strafe is true high-performance gear for serious skiers and boarders. Founded by expert-free riders (and brothers) John and Pete Gaston, Strafe was created to fill their need for gear that both performed under the most specific of conditions and looked good. Even if you're all geared-out, stop in and pick up a limited-edition baseball cap or beanie.


The premiere destination for all things mountain living. Gorsuch carries everything from high-end, high-performance gear, to beautiful decorative accessories for your second...or third home.

J. Crew at the Mountain

The mountain outpost of one of our favorite brands, seek out unique and limited-edition pieces specific to the alpine environment.

Thankfully, Aspen’s Pitkin County (ASE) airport is a quick 15-minute drive from town. The only catch is you have to get there first. Unfortunately, direct flights from the east coast do not exist (without the aid of a private jet). However many airlines have expanded their flights from many major cities. Most flights connect in Chicago or Denver. A recent search found round-trip airfare from New York is about $450 on Continental/United (but given the recent gas prices, we encourage you to shop around and book early before the snow melts and you're left in the slush).

Drive it! – The other option is get a cheap flight to Denver International and drive. Colorado Mountain Express offers transport from DEN for approximately $225 per person each way.

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