Alpine Views, Endless Adventure, and an Epic Après Scene: The 4-Day Weekend in Aspen

Maroon Bells, Aspen Colorado
Maroon Bells, Aspen Colorado Ron and Patty Thomas / Getty Images

Few states are as perennially adored as Colorado. Winter months dump blankets of powder-fine snow, pleasing skiers and snowboarders alike, while spring, summer, and fall transition locals and tourists into other adventurous exploits like mountain biking, camping, and fishing, not to mention a wealth of festivals. It doesn’t hurt that Colorado’s craft-beer scene is as epic as its après-ski options, too.

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If you’re pining for a trip to the mountains, regardless of the season, consider Aspen. Follow our four-day weekend guide for the best hot spots in town.

Aspen Meadows Resort
Aspen Meadows Resort Courtesy of VRX

Where to Stay

Aspen Meadows Resort: A Dolce Resort, Aspen Meadows epitomizes Bauhaus architecture—emphasizing pragmatic, functional design over grandeur and ornamentation. The rooms are neutral and well lit, letting the natural environment take precedence. The health club has a heated outdoor lap pool and hot tub, and complimentary rentals: bikes in the summer and snowshoes in the winter. The boutique hotel is situated on 40 acres, over which you’ll find numerous installations by Bauhaus artist Herbert Bayer. Don’t miss the dessert inspired by Bayer at Plato’s (bite-size cake covered in bright, primary-colored fondant). Enjoy it with a glass of wine overlooking the sprawling vistas of the Aspen Mountain, Aspen Highlands, and Buttermilk ranges.

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Limelight Snowmass
Limelight Hotel Snowmass residence Matt Kisiday

Limelight Hotel Snowmass: If you want to ski-in/ski-out, opt for Limelight at Snowmass Base Village. The rooms have punchier personalities than Aspen Meadows’, but they still have that classic Aspen vibe. There are also luxury residences (above) for those looking for a permanent spot mere steps from a gondola. This is an excellent spot for families, too. There’s an ice rink and the state’s tallest indoor climbing wall.

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If you really want to lean in to Aspen’s mountain-town culture, book a stay at The Little Nell, Hotel Jerome, or The St. Regis Aspen Resort.

What to Do

Winter Activities—Ski and Snowboard, Obviously: You can gain access to Aspen Highlands, Aspen (Ajax) Mountain, Buttermilk, and Snowmass with the same ticket. Snowmass is down the valley near Snowmass Village, whereas the rest are close to downtown Aspen. Start at Snowmass (if you’re not staying at Limelight Hotel and need to rent gear, go to Four Mountain Sports). It has a solid mix of beginner slopes for first-timers, as well as the option for private and group lessons. If you’re intermediate or advanced, there are plenty of steeps and cliffs for thrills. The top of Elk Camp Chair on Snowmass also has a killer vantage point of Maroon Bells. In the following days, hit up the other mountains.

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For some of the best views, don’t miss Buckhorn Cabin on Ajax to peep the sprawling Highlands Bowl—an unforgettable run if you’re experienced enough to tackle; see Aspen Chamber’s guide to skiing it like a local). After, make your way to Picnic Point for more views of Maroon Bells’ peaks. It’s also the perfect spot for a midday brew or champagne pop. Use your ski to saber the top off. (Yes, it’ll take a while. Yes, it’s absolutely worth it. Have a camera ready.) Make sure to reserve a spot for First Tracks on Ajax (every day) or Snowmass (every Wednesday and Friday). It starts at 8 a.m., and you get full access to freshly groomed runs.

Sabering champagne bottle with a ski
Sabering a champagne bottle with a ski Matt Kisiday

Take the time to mosey on over to Cliffhouse at Buttermilk for the best views of Pyramid Peak. Oh, and lest we forget the shrines sprinkled across all four mountains. You’ll stumble upon stashes of memorabilia—some pay homage to bands like Grateful Dead, while others pay respect to local legends. Make it a treasure hunt of sorts.

Spring, Summer, and Fall Activities:

There’s truly no shortage of adventure in Aspen. When crisp bluebird days turn balmy, try your hand at mountain biking (there are more than 50 miles of trails zig-zagging along Snowmass Bike Park). Bike down to the Woody Creek Tavern and cool down with margaritas (journalist Hunter S. Thompson used to frequent the spot) before cruising to the bottom. Hiking up the Ute Trail to the top of Aspen Mountain is another popular activity, as is golf, paintball, and zip-lining. Water enthusiasts can go fly-fishing and white-water rafting to boot.

Festivals: The Food & Wine Classic is a local favorite in the summertime, as is Jazz Aspen Snowmass (John Mayer is playing this year).

Shopping: For leather goods, turquoise jewelry, and custom Stetson hats (among other brands), poke around Kemo Sabe. You’ll find boutique designer labels at Pitkin County Dry Goods, Aspen’s oldest clothing retailer.

Lobby of Hotel Jerome Auberge Resort
Lobby of Hotel Jerome Auberge Resort Courtesy Image

Where to Eat in Apsen

Dining on the Mountain

Elk Camp Restaurant: Take a break from skiing to chow down on a belly-warming soup in the winter. In the summer months, take advantage of Farm to Table Tuesdays with an à la carte menu of local fare. Cap it all off with a s’more and an IPA by the fire pit. Location: Snowmass

Up4Pizza: Honestly, the fresh-baked chocolate-chip cookies are the show-stopper at this renovated patrol hut. Devour them hot and buttery, straight from the oven, or ask for some to-go (they’ll wrap them so they stay warm). Location: Snowmass

Merry-Go-Round: You’ll find tourists and locals sunning themselves on the Adirondack chairs at this mid-mountain spot. Feast on fish tacos or a hearty salad, and don’t forget a lemon bar for good measure. (Only open in the winter.) Location: Aspen Highlands

Bonnie’s: Glide on in to this mid-mountain staple (only open in the winter) for a legendary breakfast. You can’t miss the oat pancakes. Location: Ajax

NY Strip with grilled avocado and crab Oscar
NY Strip with grilled avocado and crab Oscar at TORO Kitchen & Bar at Viceroy Snowmass Matt Kisiday

Dining in Town

Clark’s Oyster Bar: Martinis, East- and West-Coast oysters, and stellar seafood options—not to mention killer sourdough bread, an irresistible chimichurri sauce, and a happy-hour burger special that can’t be beat—make this Austin transplant a smashing success.

Mi Chola: Get your tequila- and Mexican-fare fix.

Kenichi: This is the spot for world-class sushi. Get the Greentail Roll and Dynamite Shrimp.

Ajax Tavern: Drop in for casual, fast dining. We’re all about balance, so order the Ajax Truffle Fries and the Kale & Quinoa Caesar.

TORO Kitchen & Bar at Viceroy Snowmass: If you’re craving red meat, the NY Strip with grilled avocado and crab Oscar is unbelievable.

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Bad Harriet in Hotel Jerome
Bad Harriet in Hotel Jerome Courtesy Image

Where to Drink in Aspen

Bad Harriet: Venture down in the old Aspen Times building to this new speakeasy—the glittering gem of the Jerome hotel complex. Low lighting, intimate seating, and craft cocktails inspired by powerful women in history are hallmarks of the space. Drop by for pre-dinner drinks and small bites.

7908 Aspen: If you’re craving some vino, come here. The wine list has been curated by master sommelier  Jonathan Pullis, one of only 250 in the world.

Zane’s Tavern: Go here if you’re searching for a local dive bar with cheap pitchers.

Aspen Brewing Company: Sip on small-batch microbrews.

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Best Spots to Apres-Ski in Aspen

  • Schlomo’s Deli & Grill: Throw back a shotski with friends or sip on an espresso martini—either way this is a guaranteed good time at the base of Ajax.
  • The Red OnionAn Aspen saloon dating back to 1892, this is a stellar spot to crush a $2 PBR and listen to live music. You’ll forget you’re wearing ski boots.
  • The Lounge at the Limelight Aspen: Sit by the fire as you sip on cocktails and nosh on hand-tossed prosciutto crudo pizza with caramelized onions and white truffle oil. This is the best (and longest) happy hour in town.
Klaus Obermeyer at offices in Aspen
Klaus Obermeyer at offices in Aspen Matt Kisiday

Necessary Gear: What You Need to Explore Aspen

  • Smith Optics 4D MAG Goggle: Ski/snowboard goggle that offers a greater field of vision (25% more).
  • Obermeyer The Down Snowshirt: This is an essential transition layer for chilly morning hikes and everyday jaunts around town. (Obermeyer HQ is right in town.)
  • Altra Superior 4: This speedy trail shoe has a removable liner to protect your feet from sharp rocks and debris and grippy lugs that help you tear across messy terrain.
  • Bose SoundSport Free: Hike, run, bike, or hit the slopes. No matter the sport, these buds will stay put.

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