Best Time To Ski Aspen For Smaller Crowds: This is a strength for Aspen. It's not a place that gets crowded often. It avoids just about all of the day-tripper traffic on the weekends from Denver, as it's 3.5 hours from Denver (with zero traffic, which rarely happens on weekends) and 90 minutes beyond Beaver Creek. Even Denver-ites looking for a full weekend don't usually make it all the way to Aspen. So most of the skiers are destination skiers who flew in from elsewhere, or locals from the Roaring Fork TKCK Valley—there's more of them every day—who are spending a day on the slopes. In addition, there are four mountains on which skiers can spread out. The biggest crowds tend to pop up at Snowmass, whose location away from town and density of on-mountain lodging means a lot of skiers end up skiing Snowmass and nowhere else. But a busy day at Snowmass doesn't compare to one at Vail or Breckenridge. Crowds tend to be sparsest at Highlands, which locals favor for its good fall lines and the eponymous Highlands Bowl, home to one of the best boot packs in America.
Cheapest Time To Ski Aspen: Skiing isn't cheap, and skiing Aspen tends to make it even more expensive. But there are ways to get an Aspen vacation for less. First off, dates: avoiding holidays, as is the case across most of Colorado, is a must. But that's even more the case in Aspen, a place the globe's jetset seek out during those peak times. Lodging prices during winter break around Christmas and New Year's are among the highest in skiing. Same goes for President's Day and the early half of March. Outside of these envelopes, however, skiers can fish for deals, as Aspen has a good-sized lodging base. Lodging at Snowmass, about 20 minutes from town, tends to be cheaper than lodging in town. Snowmass tends to be better for some families who are seeking that all-in-one resort experience more similar to that at Vail Resorts' mountains. As with most ski resorts, it helps to have some kind of pass. Skiers eying Aspen have two options: the Ikon Pass, and the Mountain Collective. The latter has been lost in a lot of the fanfare around the Epic vs. Ikon Battle, but it remains an outstanding option, especially for skiers who take weekkend trips where they'll be skiing two or three days at most.
Best Time To Fly To Aspen: For those who can afford to fly directly into Aspen's airport, we heartily recommend it. Although it's small, the Pitkin County Airport gets a ton of service. For instance, most days in February see five flights from Chicago, multiple flights from Dallas, Denver, and Houston, and at least one from other big metros such as San Francisco, Los Angeles, Atlanta and New York. There's no other ski town that sees so many direct flights. In addition to the high numbers of options for flights, skiers who land in Aspen could, if they wanted to, walk to the slopes. The airport's proximity to town, Ajax, Highlands and Buttermilk mean that skiers don't need a car (another way to save dough). Most hotels in town will pick up their guests for free or for a nominal charge. Flying on Tuesdays, Wednesdays and Thursdays offer good discounts compared with peak days, especially Fridays and Sundays. For those not flying straight in, the drive from Denver is a stout 3.5 hours—a trade many people are willing to make for lower fares. Another option is the Vail-Eagle airport, which is about 90 minutes away, and allows travelers to avoid the worst parts of the drive up I-70 from Denver. Vail-Eagle has great directs, and it receives bigger planes than does Aspen, as it's in a more favorable spot with more room and less weather, so flights into Vail-Eagle are canceled at a far lower rate than those into Aspen. Going into Eagle the same rules apply, Tuesdays, Wednesdays and Thursdays are cheaper.