You’ve heard of Aspen. In fact, based on a highly non-scientific study I conducted which involved asking 4 of my European friends to, “name the first American ski town that comes to mind” — to which all of them replied “Aspen” — I believe that Aspen is the best known ski town in not just America, but the world. And if my data is somehow skewed, it’s inarguable that Aspen is, at the very least, one of America’s most legendary.
But legends are frequently distorted based on stories and perceptions accumulated and manipulated over time. This is often the case with Aspen, a place that is so widely known, but less widely understood.
Aspen’s legends, like all legends, are based in truth. Yes, Aspen is a playground for millionaires, billionaires and celebrities. And yes, Aspen can be more expensive to visit than other mountains. But all it takes is one trip there to see through the legend to Aspen’s truth.
The truth is, that while Aspen is most enjoyably experienced while not pinching pennies (mostly on account of the luxury hotels you’ll want to stay in and the restaurants you’ll want to eat at), it remains a welcoming, real, laid-back mountain town filled with outdoor-loving, year-round locals who are just like you and me (i.e. not millionaires). But regardless of socioeconomic status, visitors and locals ultimately find themselves here not for the glitz and glamour, but for their love of the mountains, the powder and the insane amount of trails at their fingertips (336 in all) — that’s what Aspen is really all about.
So to help you have the best time possible, check out the following introductory guide to things to do in Aspen. It features some of the best restaurants, bars, hotels, shops and winter activities in Aspen, all of which I discovered by consulting 5 trustworthy Aspen locals pre-trip and speaking with plenty more during my trip (thank you all for your help).
When you think of skiing or snowboarding in Aspen, you probably think of one place with a mountain. You wouldn’t be entirely wrong — Aspen is a town located at the base of Aspen Mountain. But when people say they’re skiing in Aspen, they’re most likely referring to Aspen/Snowmass, the mountain complex made up of 4 incredible, unique and neighboring mountains all connected by a free shuttle: Aspen Mountain, Aspen Highlands, Buttermilk and Snowmass.
Aspen Mountain: known as Ajax to the locals (the mountain’s old name). Aspen Mountain is the classic (it opened nearly 70 years ago), and with its variety of terrain, its slopes never go out of style. Plus it’s served by a gondola located right in town, allowing easy access to après at day’s end.
Aspen Highlands: just 10 minutes by shuttle from downtown Aspen, you have no excuse not to ski Aspen Highlands. Plus, it’s the locals’ favorite so you know it must be good (the expert trails and the double black diamond Highland Bowl might be why). But don’t worry, there are great trails for intermediates too.
Buttermilk: 10 minutes by shuttle bus from downtown Aspen, Buttermilk is the smallest of the 4 mountains and lives a double life — it’s known as the family or beginner’s mountain for its easier blue and green trails, but it’s also home to the main terrain park (the Winter X-Games have been held here the past 14 years).
Snowmass: 20 minutes by shuttle bus from downtown Aspen, Snowmass is massive. Topping out at an elevation of 12,510 feet and with over 3,300 acres of terrain (3 times larger than the second largest mountain, Aspen Highlands), you could spend your entire trip on this mountain alone. And with a few hotels at its base, you could stay here too.
The lifts operate from 9am to 3:30pm — so your ski day will be over by about 4pm.
Tip: The gondola at Aspen Mountain somewhat secretly opens at 8am for a small group of people who make a reservation 24 hours in advance. This’ll allow you to cut through fresh powder before anyone else. Learn more here.
When You Should Go To Aspen
The typical Aspen/Snowmass ski season runs from early December to mid April. Things tend to be quieter the earlier in the season you go (before the Christmas/New Year holiday), so if you want more space and a toned down party scene, December is for you. For optimal conditions and for an amped up party scene, try visiting over holiday weekends in January and February, or during the X Games which take place at the end of January. Pretty obvious, right?
Take a look at the map above and you’ll see that Aspen is located just west of the square state’s center — that’s a four hour drive from Denver International Airport (in good weather conditions and without traffic).
Luckily, Aspen has its own airport, Aspen/Pitkin County Airport, and it’s located just 3 miles from downtown Aspen. Seriously, you could land, get to your hotel, change and be on a gondola in 30 minutes. However, this convenience often comes with a price — a recent check of roundtrip airfare from Los Angeles to Aspen was over double the price of a roundtrip flight from Los Angeles to Denver. But remember to consider the added cost of renting a car (or paying for a shuttle), gas and your time should you be swayed by cheaper flights into Denver.
Non-Stop Flights to Aspen
While you can fly your private jet to Aspen Airport whenever you’d like (it’s a private jet parking lot on busy winter weekends), normal folk have several options for flying to Aspen during the winter season. United offers daily non-stop seasonal flights to Aspen from Los Angeles, San Francisco, Chicago and Houston. American Airlines also has Los Angeles covered as well as Dallas/Fort Worth, both with daily non-stop flights. And Delta has daily non-stop flights from Atlanta and weekly flights on Saturdays from Minneapolis.
Connecting Through Denver
If there are no non-stop flights to Aspen from your city (or you find that connecting through Denver is cheaper than flying non-stop to Aspen) don’t worry. United Express offers 10, daily non-stop flights from Denver to Aspen during winter months. The 45-minutes flight will be way better than the 4-hour drive.
Flying Into Vail/Eagle County Airport
A third option is to fly into Vail/Eagle County Airport, located about 1.5 hours from Aspen, and catch a shuttle (it’ll cost approximately $79 each way and take about 2 hours). Like Aspen Airport, there are direct flights to Vail/Eagle from several US cities as well as connecting flights from Denver.
Once You’ve Arrived
Almost every hotel in the area offers a free shuttle service to and from the airport. But if you’re not staying in a hotel, you can find a taxi, shuttle or limo provider here.
This part is pretty simple: ski or snowboard as much as possible. And with four mountains to choose from and a total of 336 trails (as described above) you’d need to move to Aspen to truly them all.
Things To Do That Aren’t Skiing or Boarding
Alright, fine I’ll give you a few more ideas. If you’re in Aspen for more than a weekend and want to take a few hours off skiing or boarding to experience the mountains in a new light, try fat biking (which is mountain biking in the snow using a bike with fat snow tires) with Sun Dog Athletics. Sun Dog Athletics also offers cross county skiing tours on the Aspen/Snowmass Nordic Trail System, which is one of the largest cross country trail systems in America, as well as 3 different snowshoeing tours. Naturalist lead snowshoeing tours can also be arranged through the Aspen Center for Environmental Studies.
Too tame? Then take a snowmobiling tour with T-Lazy-7 who offer 2 to 3.5 hour tours. Not adrenaline inducing enough? Take a tandem paragliding flight with Aspen Paragliding for a bird’s-eye view of the trails you’ve been riding.
After trying one of those adventurous activities, you may need to relax and limber up before hitting the slopes again. For that, check out Yoga for Skiers (and snowboarders), an hour long yoga session from 9:30am-10:30am held on Tuesdays, Thursdays and Saturdays at the Sundeck, the lodge/restaurant at the top of Aspen Mountain.
In the morning, depending on how much you drank the night before (see “Drink” below), you’ll want to be on the mountain as early as possible. To accomplish this, you probably won’t have time for a big sit down breakfast, so grab a breakfast burrito from Jour de Fete or a coffee and a breakfast sandwich on a bagel from Ink Coffee – both are located about one block from the Aspen Mountain gondola.
If you leave yourself enough time in the morning and aren’t b-lining it to the gondola, grab a seat at Peach’s Corner Cafe or Aspen Over Easy for a hearty sit down breakfast of pancakes, waffles, eggs or a quinoa bowl (if you’re into that sort of thing).
For lunch near the Aspen Mountain gondola, check out 520 Grill for burgers and fish tacos and Big Wrap for burritos and salads. But personally, when I get on the mountain in the morning, I don’t get off until the lifts close in the afternoon. That’s why I almost always eat lunch at on-mountain, cafeteria-style lodges like the Sundeck, located at the top of Aspen Mountain and the Merry-Go-Round located mid-mountain at Aspen Highlands.
Tip: At both Aspen Mountain and Aspen Highlands, you don’t need to ski all the way down to the base of the mountain until you’re ready to end your day (you take the gondola to the top in the morning, ski down to about half way, take a chair lift back to the top and repeat. If you want to take a longer lunch break and ski all the way to the bottom of the mountain, grab a burger at Aspen Mountain’s Ajax Tavern or a pizza and a beer at Aspen Highland’s The Highlands Alehouse – both of which are located directly at the bottom of their respective mountains.
For dinner, there are endless options from casual to high end. Lets start with The White House Tavern, specifically their chicken sandwich (pictured above). Go there. Eat that. Thank me later. Keeping it casual head to Irish bar, Finnbarr, for pub fare, beer and a good selection of whisky. Moving up the price scale, try Nantucket-inspired seafood restaurant, Grey Lady, Italian restaurant, L’Hostaria, and French bistro, Cache Cache.
On the highest end of the spectrum, don’t pass up a meal at Chefs Club by Food & Wine at the St. Regis Aspen, where chefs from Food & Wine’s Best New Chefs list create and curate new menus on an ever-changing basis, and Matsuhisa, which dishes out the best sushi in town.
The adventure doesn’t have to stop when the lifts close. On Tuesdays and Thursdays, take a 30-minute long snowcat ride up Aspen Highlands for dinner at the legendary Cloud 9 Alpine Bistro, a small chalet with a wood-burning stove that’ll make you feel like you’re hidden away in the Swiss Alps. Cloud 9 is also open for ski-in ski-out lunch everyday, but be warned, it’s pricey.
For a dinner outside of town and one you’ll have to work for, try Pine Creek Cookhouse, where the only way in is to cross country ski (with the aid of a miner’s light attached to your head) or by horse drawn sleigh.
Like the snow, the booze in Aspen is plentiful. Drinking on the mountain begins with finding The Oasis, a roving, pop-up champagne and caviar bar set up on Aspen Mountain on Fridays, Saturdays and Sundays. Follow The Little Nell’s Twitter account and the hashtag #AspenOasis for clues to its current location.
Aside from hidden champagne bars and a beer during your on-mountain lunch break, the real drinking begins around 4pm after the ski lifts close.
Your first stop is Ajax Tavern, located directly next to the Aspen Mountain gondola. Grab a seat outside, a Colorado brewed beer and an order of truffle fries. Next door, take it up a notch at Sky Hotel’s 39 Degrees, which is frequently called Aspen’s best après ski party. Now, head back to your hotel for a brief break and a shower.
Tip: Aspen may seem trendy and stylish, but its bar scene, even the nicest bars, are casual — so don’t show up over dressed (remember, this a mountain town and you can’t go wrong with jeans, a flannel shirt and a coat).
For a pre or post dinner drink, head to the old timey Justice Snows and select a specialty cocktail from their 95+ item, leather bound bar menu. Keeping on the classic Aspen atmosphere train, head to J Bar at Hotel Jerome, which was built and opened in 1889. Swing by after dinner and try the Aspen Curd (a.k.a the whisky milkshake).
Next, keep the party going at Jimmy’s, a local favorite bar with strong cocktails, Eric’s Bar for billiards and cigars, and Aspen Brewing Company, a small tasting room featuring delicious local brews (their Belgian Farmhouse Saison won the Gold Medal at the 2o14 World Beer Cup in the French & Belgian Saison category).
If it’s late, you’re drunk and looking for a club vibe, Bootsy Bellows, the L.A. club’s Aspen outpost (you might be able to understand what you’re in for just based on that description) fits the bill. And if it’s live music you want, check to see who’s playing at Belly Up during your time in Aspen. The tiny yet legendary music venue has hosted intimate performances by the likes of The Flaming Lips, Snoop Dog, Jimmy Buffet and John Legend among countless others.
If you’re anything like me, you’ll want to spend as much of your time in Aspen either on the mountain, relaxing in a nice hotel or leisurely eating and drinking. But for any downtime you for some strange reason find yourself with, Aspen isn’t short on places to shop.
Skip the ultra luxury shops and head straight for Pitken County Dry Goods, which has been stocking mens sweaters, jackets, jeans and more since opening in 1969. And while you may like to splurge on travel, you’ve always appreciated a good deal — so after PCDG, swing by The Thrift Shop of Aspen to score some barely used designer threads. If you’re a lady and this meager section leaves you wanting more, I suggest you check out Lucky Magazine’s Aspen shopping guide.
If it’s your first time in Aspen, you’ll want to stay in downtown Aspen near the base of Aspen Mountain. There are only a few hotels to choose from and it’s difficult to go wrong with any of them, but for my first ever trip to Aspen, I choose the legendary St. Regis Aspen.
The 179-room hotel is located just two blocks from the Aspen Mountain gondola and two blocks from the center of downtown Aspen. While the walk to the gondola is easy, this is the St. Regis after all, so just hop in one of hotel’s black Escalades which are always ready to shuttle you back and forth.
Inside, the rooms feature a soothing neutral color palette of light grays and off-whites, offset with chocolate leather accents like a leather headboard and a leather lined Ralph Lauren desk. Many of the rooms feature a mountain view and I stayed in a second floor room with a large balcony and incredible view of the slopes. Let me tell you, there’s nothing quite like waking up to the mountains at your doorstep.
Outside of the lobby, there are 2 constantly roaring fireplaces and on the terrace above them, a heated pool and 3 hot tubs. Going for a swim and sitting in one of the hot tubs after a long day of snowboarding, while fresh snow is falling from the sky, is an experience you need to have — trust me.
Lastly don’t leave without trying a Downhill Snapper, the St. Regis Aspen’s signature Bloody Mary. I made my own with the mini Bloody Mary bar that was waiting for me in my room when I checked in. Best. Hotel. Welcome. Gift. Ever.
Located directly next to the gondola, making it Aspen Mountain’s only ski-in ski-out hotel, is The Little Nell. Right next door and home to a popular après ski scene you’ll find Sky Hotel. A few blocks deeper into downtown Aspen (requiring a complimentary shuttle ride to and from the mountain) is the historic and stylish Hotel Jerome. And located about a block behind the St. Regis, there’s the eco-friendly Limelight.
There are also a few hotels, like the Viceroy and the Westin, at the base of Snowmass (both are ski-in ski-out). If it’s your first trip to Aspen, I’d recommend staying in downtown Aspen and taking the shuttle over to ski at Snowmass for a day. If you find Snowmass is more your style, you can always stay there on your next trip.
You worked hard conquering the slopes. You bounded through fresh powder, you maneuvered around trees with skill and you may have even done the ol’ yard sale once or twice. While all this would warrant a spirited pat on the back at some other mountains, in Aspen, it warrants a rejuvenating full body massage. And there’s no better place to indulge in a massage than at Remède Spa at the St. Regis Aspen, which was voted the best spa in the world by Travel+Leisure. Allow me to repeat that — in. the. world.
I’m no fool, so I made sure to end my weekend in Aspen with an expertly administered and customized full body massage at Remède – but not before sipping champagne and putting the spa’s oxygen lounge, steam cave, hot tub, cold plunge pool and confluence waterfall room to good use.
When my massage was complete and I gently returned to reality with my snowboarding-inflicted aches now soothed away, I was ready to rewind the weekend and do it all over again (and again and again). But the real world, as in the world outside of an Aspen ski vacation, unfortunately required that I return.
Extra: What to Wear
To get the most out of Aspen, you need to be prepared with the right gear. To help you with that, go check out these TMT articles: Aspen Winter Style Guide featuring Eddie Bauer and Winter Gear Essentials: What I Wear On The Mountain.
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Photo Credit: Top photo by Jeremy Swanson. “The Basic” photo by Aspen Chamber of Commerce. “Play” photos by Aspen Skiing Company. “Getting There” photo by ColoradoDotPhoto. “Eat” photo by Jessica Greenfield. ”Drink” photo by Nan Palmero. ”Stay” and “Relax” photos by St. Regis Aspen.
Special thanks to Aspen/Snowmass and St. Regis Aspen for hosting me during my stay. All opinions are entirely my own. Seriously, I want go to Aspen at least once a moth and re-trace everything I mentioned in this article…but I’m not a millionaire (yet).
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