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Snowmass is similar to a Vail resort, more crowded and vanilla but a good park. Aspen highlands is sick, basically a blue run with steeps off both sides the whole way down. Aspen is one of my favorite places to ski, extremely underrated and made fun of but I honestly hope it stays that way.
What? I've never waited in line at Snowmass for more than a couple minutes on the busiest day of the year. And that was only at one lift. Much longer lines at the gondola for Aspen Mountain for sure. People that say Snowmass is flat haven't taken the time explore. There's a reason they hold the Freeride tour there. Having one of the best parks in the world is just a bonus.
you obviously have never actually ski'd snowmass. as thelorax said, there's a reason they hold a freeride comp there. Highlands isn't even that exciting, sure the bowl is huge but it's not even that gnarly besides being a consistent 45~ degree pitch.
Aight, I'll lay i tout for you guys since I want anybody going all the way to Aspen for a trip to enjoy it.
Buttermilk: Go there for the best park/half pipe in the world next to Keystone but don't expect any good terrain outside of the park. There's some fun tree runs and if yo have some BC knowledge and the necessary BC equipment, dropping off the backside is fun.
Aspen Mtn: Great skiing, fast laps and tons of vertical thanks to the Gondola and Silver Queen. Amazing tree runs, a few technical and very steep double blacks. What I love about the skiing at Aspen Mtn is that all of the more difficult runs are weird-off piste angles that are sure to make you think a lot more than you would on a standard double black. You'll look at it and likely think "damn, I've never skied a slope of this aspect before". Lots of hidden memorials for dead musicians where you can find locals smoking lots of cannabinoids. Aspen Mountain will also have the most fur wearing pretentious European and Texan tourists of any of the 4 mountains. If you can get past that, the locals are some of the most awesome people you'll ever meet. There is no park here. You don't come here for park.
Highlands: This is the local's mountain. Also no park except in the late spring there's occasionally a few boxes after Buttermilk closes. SOme of the best steep and tight tree skiing you'll ever experience and if you like skiing groomers, these are some of the most fun you'll ever have ripping down the main runs on any ski resort. Hiking the bowl is a must. If you ski the gut down it's the steepest way to do it, but I prefer to traverse the ridge over and drop into what's called the G-zones along the treeline.
Snowmass: This is probably the most marketed and "touristy" of the 4 mountains but if you've ever been to Vail, Park City, or any other large and famous ski resort, and then come here you'll think it's empty in comparison. It's got the biggest ski school of the 4 mountains (I used to teach in it), so the base area has the appearance of being a crowded shitshow in the AM but it clears out real quick once the kids get in their classes in the AM. If you want a variety of skiing, you literally cannot find a better mountain that has this diverse of terrain. Steep chutes, open bowls, tight trees, super steep trees, couliors, smoke huts, huge pillows, and even a 5 mile long run. Also one of the best parks in the country.
Since it's remote and off the i-70/Summit County corridor it's hard to find deals but in the spring they have a bunch of deals for stay and ski free. if you are in college they have a great college deal too. go on vrbo.com and find places to stay. hell, maybe you'll end up renting my family's place.