Best Things to Do in Aspen

If it’s winter and you’re in the pursuit of fresh powder, you’re going to find it here. Aspen Snowmass ski resort isn’t just one mountain, it’s four, with more than 5,500 acres for shredding across the bunch. Aspen Mountain (a.k.a. Ajax), is the only one directly in downtown Aspen, and it offers intermediate terrain. The others, all slightly outside of town, but connected by a free bus system, are Buttermilk (good for beginners), Highlands (expert-level runs) and Snowmass (the most family-friendly choice with the most varied terrain). If you’re here in the summer you can also catch a lift up Aspen and Snowmass for hiking, mountain biking and frequent concerts. 

One of the most scenic drives in the West, Independence Pass connects Aspen with Twin Lakes. At the highest point drivers are at 12,095 feet, and from the pull-out there you can see myriad other peaks, dense forests of aspens, alpine lakes and the other drivers white-knuckling many the hairpin turns of the pass. 

Note: Independence Pass closes during the winter season. The steep, serpentine road is too treacherous to attempt when the conditions are icy. 

Said to be the most photographed peaks in North America, the pyramid-shaped twin mountains of North Maroon Peak and Maroon Peak are best shot just after sunrise, when the two fourteeners are cast in a brilliant pink and orange light. If you stand at the far end of the lake, it’s possible to capture their reflection in the water. However, don’t fill up your memory card here — there are a handful of great hikes spidering out from the Visitor Center that deserve time and space too. 

Because it’s so popular, reservations are required for parking at the trailhead. However, if you don’t score one of the coveted few spaces, you can take the shuttle, which runs every 15 minutes from Aspen Highlands, or cycle your way there. 

This free 25-acre wildlife sanctuary on the shores of the Roaring Fork River has some of the best trails in the Hunter Creek Valley. The Aspen Center established the area with a goal of conservation, so there’s frequently naturalist guides leading hikes and snowshoe tours. There are also raptor (eagles and owls) demonstrations and programs for kiddos.

One of the best places to catch a live show in Aspen, this intimate (read: absolutely tiny) club has seen the likes of Twenty One Pilots, K’naan, The Beach Boys, and Diplo.

Whether it’s 70 degrees and bluebird or dumping snow, it’s always a good time to visit Aspen’s lone brewery. Be sure to ask for a flight — it comes on what can only be described as a mini shot ski board. Their semi-covered patio is also dog-friendly. 

Once upon a time, cowboys rode their horses directly into this saloon housed in the historic Hotel Jerome. While it does have a bit of a Wild West vibe, today it attracts a more well-heeled crowd with its extensive whiskey wall, craft cocktail menu and $28 burger.

Considering it’s the country’s most premier gastronomic festival, the Aspen Food & Wine Classic (which will be held June 17-19 in 2022) often sells out months ahead of time. The three-day festival sees cooking demonstrations with celebrity chefs like Martha Stewart and Andrew Zimmern, endless wine pours and the kind of opulent revelry that only Aspen can bring. If you go, remember to pace yourself — this is a marathon weekend of chomping and chugging.

For three days each January (21-23 in 2022), some of the best winter skiers and snowboarders from around the world descend on Aspen to compete in this extreme athletic competition. Everything from the superpipe to slopestyle takes place on Buttermilk Mountain and is open to the public. 

Given the name, it should come as no surprise what the signature foodstuffs are at this eatery. Whenever possible, the restaurant tries to source locally and seasonally, though the recipes have a more global bent (one example: bison schnitzel). If you’re on a budget, pop in between 2:30 and 5 p.m. when the cheese and charcuterie boards are a bit cheaper. 

Though it’s been open less than a year, Casa D’Angelo is already making a name for itself as an authentic Italian restaurant. The wine list is also very extensive, which makes sense considering the owner also has a vineyard in Italy. Given its second-floor patio seating with views of the mountain, it’s a great place for a sundowner. 

Considering it’s found at 11,000 feet and occasionally obscured by clouds, this bistro occupying a former ski patrol hut has an appropriate name. The things that happen inside… Well, they may be less appropriate. No matter the time of day, there’s a good chance the patrons will be dancing on tables in varying degrees of undress and spraying mind-bogglingly expensive champagne. Though the floors may be sticky, don’t expect bar food. Menu items include things like lobster and king crab bouillabaisse and rack of lamb.

One of the most iconic eateries in the area, Woody Creek Tavern is the place where aging hippies and Aspen socialites converge. Whether that’s because of its dangerously strong margaritas or because it was reportedly the favorite watering hole of Hunter S. Thompson, we’re not sure. With Christmas lights draped across the ceiling, leopard-print bar seats, walls papered with Polaroid photos signed by locals and guests and a taxidermy buffalo head that wears a too-small cowboy hat in the corner, it’s a fun place to hang out and people-watch over a plate of fish tacos. 

This 40-acre property was originally the headquarters of the Aspen Institute, but now it’s a chic, art-forward hotel, with multiple indoor galleries, as well as a massive sculpture collection that’s scattered throughout the grounds. It’s a little outside of the downtown core, but if you’re looking for a less rambunctious getaway, that might be ideal. 

The only true ski-in/ski-out hotel in Aspen, The Little Nell is constantly buzzing with activity. Considering the hotel also holds a handful of restaurants and bars (including a swanky speakeasy hidden behind a bookshelf), it’s something of a meeting place. If you do stay there, expect a room with a fireplace, a balcony overlooking either the town or the mountain and a very well-stocked minibar with free nonalcoholic drinks and snacks. 

The Hotel Jerome has a lot of interesting bragging rights. It’s been open since 1889, was the first hotel in Aspen, was the first west of the Mississippi to have electric lighting and was the campaign headquarters for Hunter S. Thompson during his infamous (failed) run to become the sheriff of Aspen in 1970. The three-story redbrick building has a bit of an eccentric vibe, with taxidermy festooning the walls, ample leather accents and staff dressed in cowboy attire.