Ok, so here is a review on all 3 Madison area ski hills in one. I grew up skiing in the midwest, and have been doing so for nearly 29 years. I have skied all over Wisconsin, Minnesota, Michigan, Colorado, Utah, Wyoming, and California. So, this review will be from the point of advanced skier/boarder/tele. I love real double blacks and the backcountry, but I also need to get out and slide on my boards just to get whatever fix I can, as I live in Madison. All of the "black" or "black diamonds" in Wisconsin/lower-midwest are really western blues or blue-blacks (except maybe Damnation up at Mt La Crosse, and a couple of very short blacks and some glades up at Granite Peak/Rib Mountain).
When at Tyrol Basin, the skiers far left, lift "C," there is some decent terrain, in between Yodeler and Double Diamond, right down the lift line. If there is enough snow, you can ski some trees with a solid level of steepness. When the snow is deep enough this is my favorite terrain to ski out of the 3 ski areas, however, winters have not been kind lately, so this bliss is increasingly rare. TB also generally has the most varied features and park, which I certainly enjoy (as long as the park is not crowded with tweens, a rare occasion here, since it is the closest to Madison, and has the best lift-ticket deals). Also, you can generally find a pipe here. TB has the best bar in my opinion, but the lowest marks for overall infrastructure. Also, the parking lot is kind-of a pain at the end of a long ski day. Overall, TB has the highest bang for your buck though, as you are not paying for all the infrastructure.
The "blacks" at Cascade (CM) are the best, as compared to Devil's Head (DH) and Tyrol Basin (TB). Cascade, is by far the busiest, but also the easiest to access (especially for IL patrons). Although it is the busiest, the lift capacity (especially high-speed quad) is high enough that it usually isn't any worse than the other hills. Cascade has probably the largest and most varied infrastructure, with 2 lodges at the base and the Daisy lodge up top. One thing that I like about CM is that their best runs, Cindi Pop, Screamin Steven, and Pike (or something like that) are all serviced by the Cindi Pop lift. This segregates out the majority of the beginners, and allows one to take run after run with little in the way of lift line or rental-mentals to dodge, even on busy days (sorry couldn't resist the jab, I realize that I once was also one ;-). Also, North Wall, Mogul Monster, and Manitou have good terrain, all be it generally much busier. Rail features are plenty at CM, but solid kickers or a pipe are generally not present (strangely enough they do have a pipe dragon, but apparently the amount of now that they need to build a pipe, is prohibitive)
You will get the longest runs at DH, but they have very little in the way of really steep runs, and I often find my self making very few turns here, so as not to kill the speed which I crave. Skiers far left at DH is where you will find me if I go here. I cant remember the names of the runs, but there are a couple spots that you can drop some small rock out-croppings, and there are a few steep spots here. Most of the blacks at DH are really midwestern blue-blacks. DH does have some of the better kickers that I can remember, and also a solid representation of rails. DH also has a pretty good lodge system and set of bars, as one might expect from a full-out resort setting. I have never rented, so I cannot comment on that. This is probably the most out of the way of the three. Only other complaint with DH, is that it can be a bit spread out, too much skate-skiing to get from one side to the other. If there is fresh snow, DH is even slower, however fresh snow is when I head to TB or CM.
Overall, the 3 Madison area hills are a great option for S Wisconsin and IL people. Chestnut isn't bad in this respect either. Skip Sunburst, Christmas Mt, Alpine (unless it is a concert), etc. and make the trip to CM, TB, or DH. Otherwise head up to Michigan, Indianhead, Mt Bohemia, etal, and stop at Granite Peak on the way. Or head up to Lutsen and stop at Mt Lacrosse, Afton Alps, and/or Welch village on the way. Gotta get it how you can! Hope this helps. read more