If You Only Have Three Days in Aspen, Colorado…

These are the places to stay, things to do, food to eat and cocktails to drink if you only have a long weekend to spend in Aspen.


Words by Kevin Gray.

If Aspen is three things, it’s: a ski town, a playground for the wealthy and the kind of place you find yourself checking real estate listings after you visit—regardless of how far-fetched that move might be.

Established as a mining camp in the late-1800s during the Colorado silver boom, and later revived as a ski destination, today Aspen is home to a modest 7,000 residents. It maintains a charming, small town feel despite the fact that it draw tens of thousands of visitors from all over the world during its peak seasons. Combine all that with an idyllic location situated along the Roaring Fork River in the Western Rockies, and you’ve got a fine homebase for exploring the town itself and the surrounding area.

So pick a weekend in your near future, and make it a long one. Because we’ve got all the intel required to spend three memorable days in Aspen. First up: a place to rest your head.

Where to Stay
If you want to splurge on a hotel, well, that’s easy to do in Aspen. The St. Regis is nestled at the base of Aspen Mountain and channels an old world aesthetic, but with all the modern trappings. Lounge by the pool, sink into the top-notch spa and have dinner at the Chefs Club restaurant, which features 20 signature dishes from 20 different star chefs (think Eric Ripert and Mario Batali). And here’s something fun: each day, the St Regis sabers a bottle of champagne to signify the transition into evening. So position yourself nearby at sunset, and enjoy a gratis glass of bubbly to start your night.

Image courtesy of the St. Regis Aspen Resort.

The recently-renovated Little Nell is an inviting hotel sporting 94 guest rooms, gas fireplaces, private balconies, original artwork and some of the best service around. Visit the on-site Adventure Center, and let the knowledgeable concierges customize the perfect outdoor excursion, from mountain biking and fly fishing to stargazing tours.

For something more historic, there’s Hotel Jerome, which has been an Aspen landmark since 1889. Located right on Downtown’s Main Street, the upscale boutique—with its recently renovated guest rooms—is a comfortable spot to base your stay.

Plenty more options abound, from big names like the Hyatt and Kimpton’s Sky Hotel to numerous condo rentals. And that’s just in Aspen proper. Venture a few miles away to Snowmass, and your choices increase in number, while often decreasing in price.

What to Do
Start by going outside. Look around. See all that gorgeous surrounding nature? That’s your playground.

Hikes are plentiful, and include the challenging Ute Trail as well as relaxing, scenic walks around the iconic Maroon Bells, which should be at the top of any Aspen to-do list.

Image courtesy of Snowmass Bike Park.

If you’d like to speed things up, skip over to Snowmass and hop on a bike. The 50 miles of cross-country trails are supplemented by the Snowmass Bike Park, which features beginner runs as well as expert-only downhill adrenaline rushes served via gondola.

Since Aspen is situated along the Roaring Fork River, white water rafting is a popular way to spend half a day during summer visits. Book in advance with one of the several outfitters to ensure your spot. Level-three rapids are the most common option and suitable for families, offering thrills for adults and kids alike.

And, of course, you can (and should) ski. Aspen has four mountains, including Aspen Mountain, Aspen Highlands, Snowmass and Buttermilk. If you’re an expert, Aspen Mountain has the slopes for you. Snowmass has the widest variety of trails, and Buttermilk is the best bet for beginners.

What to Eat
Fortunately for the hungry traveler, most of Aspen’s best restaurants are located right in Downtown, so you don’t have to go far to eat well.

Breakfast starts at Jour de Fête, a casual, French-inspired cafe for coffee, croissants, scones and breakfast sandwiches. Spring Cafe has all your healthy-leaning bowls and juices. And Justice Snow’s has ricotta pancakes and bottomless mimosas because, hey, you’re on vacation.

Image courtesy of Ajax Tavern.

For a casual lunch that still keeps things interesting, Meat & Cheese is flush with charcuterie boards, fresh salads and two-handed sandwiches. Located in an old mining cottage dating back to 1883, White House Tavern grills a mean burger, and is a popular spot with locals. Get there early, or risk a growling stomach as you wait in line. And for something al fresco, Ajax Tavern is the place to be. With an expansive patio and great views of the mountain, it’s a fine choice for lunch or an apres-ski drink.

As for dinner, Jimmy’s is a local institution that’s been serving perfectly-cooked steaks, fish and all the accoutrement since 1997. For a classic meal and stellar wine list, you’re in the right place. And just a few doors down is the newer Jimmy’s Bodega, an offshoot that features fresh oysters and a seafood-heavy menu alongside a menu of craft cocktails inspired by the proprietor’s travels to places like Japan and Oaxaca.

Octopus a la plancha. Image by C2 Photography. Courtesy of Aspen Kitchen.

For something fun and casual, try the second-level Aspen Kitchen, which sports three walls of glass for good views of the mountains, and an expansive terrace for better ones. And lest you think this place is all views, they’ve got food, too—contemporary American fare like housemade charcuterie, suckling pig and dry-aged ribeyes.

And if it’s a special occasion, or you just really like fish, reserve a table at Matsuhisa. Chef Nobu’s menu features Japanese food with South American accents, and includes a variety of hot and cold dishes alongside the freshest sushi and sashimi.

If you’ve got some energy after dinner, check out The Living Room inside the Hotel Jerome. Grab a seat at the bar or find a plush chair near the fireplace of this gorgeous lounge, and order a well-deserved cocktail.

Or venture over to Hooch, which offers an expansive spirits collection and some of the best drinks in town that range from tried-and-true classics to inventive seasonal concoctions.

Of course, sometimes you just want a beer and a bar stool. For both, check out the Red Onion. Another historical gem (this one dating back to 1892), the casual bar stays open late, catering to locals and visitors alike with cold beers, lots of bourbon and all the wings and sliders that pair so nicely with both.