Tucked away in the Northwest corner of Illinois on a high rocky bluff overlooking the Mississippi River near the tourist town of Galena is the Chestnut Mountain Resort. To the rest of pancake flat Illinois, the appeal of this section of the state are the hills, valleys, bluffs and large rock faces found in here. The last ice age somehow missed this area of the state. Thus the ski resort takes full advantage of what the glaciers missed.
So on the last day of their season I visited with my “Team” (Spencer 7 and Sam 5). The resort was in a festive mode for Easter, and even more so for the jubilation that comes when a long season comes to a close. Lots of hi fives and hugs all around and not just from the Easter Bunny.
Surprisingly, the area was still almost 100% open. Winter storms had been good to the area this year and provided some nice snow dumps. Add to that cold weather that allows for the 100% snowmaking to crank out the white stuff. So on this last day of the season there was enough frozen granular to go around. The coverage was so strong I am sure they could have remained open a few more weeks if the demand was there.
But in speaking to the Marketing Director Stewart Stoffregan, the demand was “really not” there. Post-Easter skiing is a hard sell in any market. Easter’s early arrival this year resulted in an even shorter demand cycle. Thus the resort decided to close for the season the day before Easter. Nevertheless, the bright sunshine and great views of the Mississippi river made for a fine day of skiing.
This is not your typical Midwestern ski bump. The terrain here is steep and rocky. The trails are really carved out of a bluff. The resulting pitches are so steep that they seem to take the resort’s 475 feet of vertical in one drop. This is a trail map that poses a challenge.
Typical of most “upside down” resorts, beginner terrain is limited to a few flat spots on top. “Old Main” is the only green trail that runs top to bottom. It is really a wide gully that has been bulldozed down the bluff. Steep rock walls loom on either side of the trail. My boys nicknamed it “the canyon” as that is what it felt like.
![]() |
The trail map doesn’t do justice to the steepness of the Chestnut terrain. Photo provided by Chestnut Mountain.
|
The rest of the trails are steep fast blues and challenging black diamonds. “Warpath” and “Crazy Horse” are two of the steepest trails I have found in the Midwest. They skied more like something you would find in Northern Vermont rather than Northern Illinois. Add to this an excellent mogul field on “Eagle” and you have some challenge here that will entertain the most jaded East Coast skier.
There also is a large terrain park area located off to the side of the main ski area called “The Far Side.” It is serviced by two rope tows. Here Chestnut sets up a large terrain park with many hits and jumps. This area is heavily marketed toward the snowboard and twin tip crowd. There is a half pipe and some smaller hits on the main area as well. However most of the main area is so steep that it is more apt for shredding than pulling tricks.
![]() |
Dropping down Eagle toward the river. Photo provided by Chestnut Mountain.
|
The resort’s main trails drop almost straight down to the river’s shoreline. The slopes are only separated from the river by a very active railway (and a large fence). Several trains passed during the day with their whistles blaring. Also several tow boats were visible pushing barges on the wide Mississippi. Thus not the most remote feeling resort, but great entertainment for a couple of elementary school kids.
![]() |
The “team” on the chair (note river and railway in background). Photo provided by Robbie Allen.
|
Chestnut Mountain Resort is a year-round location. They offer mountain biking, birding and cruises on the Mississippi in the non-snow months. The resort has a large lodge located directly above the slopes. Both the rooms and the dinning area offer excellent views of the river and the surrounding terrain.
Overall this was a great day of skiing. This resort offers some real challenges. My Team snowplowed down some of the steeper stuff under Dad’s watchful eye. I then swooped down enjoying the run and catching up with them at the bottom. The snow held up for most of the day but had become soft by the closing bell.
We greatly enjoyed our day and even found a few Easter eggs in the resort’s hunt late in the day. The best find was some real strong terrain where it would not be expected.
Robbie Allen is an avid small hill skier. He has written several articles on the many small hills he has sought out.
Join the conversation by logging in.
Don't have an account? Create one here.