layout, lifts, size, variety, affordability
some poling required, town disconnected from base village
No matter your skiing ability, there is plenty to keep you entertained at Winter Park. Perhaps the best feature of the mountain is the way it is laid out, which especially benefits families. There are very few places where experts and beginners will cross paths, and the terrain is divided into multiple pods where five to ten runs return to the same high-speed lift. For families or anyone who just loves a smooth, groomed run, I highly recommend the terrain off of the Olympia Express and High Lonesome Express lifts. These areas contain only green and blue runs, so you don't have to fear being run down by a bored expert flying past you.
Of course, everyone knows about Mary Jane, and if you enjoy bumps or long, consistently steep runs, you will likely spend most of your time here. For me, Mary Jane trail is about as good as any run anywhere. It's usually half groomed and half bumps, so everyone is happy, and it just goes on and on.
Parsenn Bowl is breathtaking, and for a blue cruiser like me, it's also heaven. These are the longest runs on the mountain, and the bowl is served by a high-speed six pack, so you can make laps with just the right amount of rest on the lift. They do a good job of leaving some runs natural while grooming others. I could ski a different line in this bowl all day long without getting bored. One note of caution though: do not get stuck here on a cold, windy day. The top third or so is completely exposed, and that lift ride is brutal in the wrong conditions.
I heard a ton of good things about Vasquez Cirque, but since I don't go out of my way to ski blacks, I didn't check it out myself. This is another example of great layout at Winter Park, because that section is hard to get to and only has expert stuff, so different skill levels don't cross. As for Vasquez Ridge, this area is a hidden gem. Though you will have to pole at the bottom of these runs, these blues are worth it. My wife and I got to make the first tracks down Buckaroo one morning after about three inches fresh on top of grooming. I don't know what heaven will be like, but I hope it's similar to that. I floated the entire way down, making huge GS turns with a smile on my face.
The last thing I'll say about Winter Park is that the base-area lodging is incredibly more affordable than other Colorado resorts. They have the expensive slopeside condos if you want, but they also offer three high-quality affordable options within walking distance of the base and multiple choices in town (2 or 3 miles away). We actually stayed at Iron Horse Resort, which has ski in-ski out access along a trail connecting the base of Mary Jane Mountain and Winter Park Mountain. The great thing about this location is that it allows you to end your day at the bottom of Mary Jane Trail. That's a pretty darn good way to finish.