CHESTNUT MOUNTAIN RESORT Review — A Warm and Welcoming Winter Getaway

Slopes for beginners, intermediate skiers, and professionals mean there's something for everyone at Chesnut. Chestnut Mountain resort

“I can’t take on those Black Diamonds yet...”
“It’s your first time on the slopes?”
“When you want to slow down, just remember: pizza!”
“You think you’re ready to take on Old Main now?”
“Pizza! Pizza!”
 “Man, Crazy Horse was awesome!”

It’s All About the Skiing

Looking around the grounds of Chestnut Mountain Resort in January, there are three things you’re guaranteed to see: snow, skiers, and snowboarders. Snow machines whir, magically kicking frozen precipitation up into the air, and people of all ages enjoy the resort’s nineteen runs. Some skiers lounge in between runs, watching others from the large bay windows of Chestnut’s restaurants that overlook the slopes.This reviewer--a skiing neophyte--was particularly struck by the sheer number of children zipping around the slopes, many without a need for ski poles at all! Fearless, poised, and thoroughly loving it, they could be found throughout the runs, enjoying the clear skies, brisk air, and even the ski lifts. Clearly, it’s never too early to learn to ski, and at Chestnut Mountain Resort, it’s all about the skiing.

Hit the Slopes by Ski or Board at Chestnut Mountain Resort

While most visitors to Chestnut you come across will be tackling the slopes on ski, snowboarders are also popular with some. If you’re interested in trying one or the other, but aren’t sure where to start, Chestnut offers private and group lessons for all skill levels. At a group lesson, you can expect patient, friendly, and clear instructions--even if it’s your fourth time biffing it on the Rookie slope! Snowboarders, especially, it seems, get used to such falls by the very nature of how they stop, so as we watch in amazement as beginners take to the slopes with their snowboarding instructors, getting up from a seated position is one of the first things they practice.

The jacuzzi tub was a wonderful treat after spending time in the winter weather! Photo provided by Chestnut Mountain Resort
Learn to snowboard or ski at Chestnut -- lessons and rentals are offered!

A MidWest Mecca

Expect to see visitors who hail from eastern Iowa, Chicago, or suburban Illinois at the resort. Some are weekenders who live right across the Mississippi river and come frequently, while others may have made the drive from the Windy CIty for a getaway with friends or loved ones. If you’re visiting during a Friday in January, you may see hundreds of middle schoolers flock to the resort for an annual school skiing trip. If your time does overlap with such a large party, fear not! The staff can handle crowds without you ever feeling like you’re waiting a long time for your turn on the slopes or lifts. Chestnut is a popular destination for couples of all ages, too--several pairs “double dated” at the chalet, sharing meals and slope time together.

Tips for your trip:

  • Do take advantage of Chestnut’s hot tub and sauna to keep your muscles from getting sore.
  • Do pack snow pants and expect to fall if you’re just starting out
  • Do take a lesson to brush up on your skills--earlier lessons will get you more individualized attention
  • Do try the horseradish whipped mashed potatoes at Sunset Grille
  • Do take advantage of the ski racks in each room to hold your gear
  • Don’t worry about looking out of place--the staff helps you stay informed!

Chestnut Mountain Resort, located in Galena, IL, bills itself as “The Midwest’s Premier Year Round Resort.” If Chestnut’s summertime offerings are as well-run as its winter options, in this writer’s view, travelers interested in outdoor fun should find plenty to enjoy whenever they visit the resort.


P.S. Curious about who said "Pizza! Pizza!" on the slopes and in what context? Nothing more than a friendly staff member repeating the mnemonic device many are taught when learning how to slow down on skis, thanks to the pizza like shape the skis form as you dig in to reduce your speed.

The nachos from The Summit Sports Bar were so good you may want to get them a second time! Perfect to recharge while watching others through the restaurant's large bay windows. Photo by Brent Ervin-Eickhoff
Even on beginner slopes, you're bound to feel the rush of skiing as you glide down the slopes


Reservations to Chestnut Mountain Resort are available year-round.


Reservations can be made online at Chestnut Mountain Resort's website.


Chestnut Mountain Resort
8700 W. Chestnut Mountain Rd
Galena, IL


Photos provided by Chestnut Mountain Resort, unless otherwise noted.

Brent Ervin-Eickhoff
Brent Ervin-Eickhoff is a director, writer, and educator based in Chicago, IL. He has worked with A Red Orchid Theatre, Silk Road Rising, Mary-Arrchie Theatre Co., Facility Theatre, and others as a director, assistant director, and in a variety of artistic capacities. Brent served as Co-Artistic Director and then Managing Director of Blue Goose Theatre Ensemble for three years, of which he was a founding member. His productions of Herculaneum and Bison? Bison. Bison! with Blue Goose were praised by critics and audiences. Bison? Bison. Bison! was selected and performed as part of Chicago’s Night Out in the Parks Initiative. An award-winning filmmaker, Brent’s films have screened as part of the Frog Baby Film Festival and Indianapolis 48 Hour Film Project. His play Puget Sound was workshopped as a staged reading as part of A Red Orchid Theatre’s Incubator Program in 2017. Brent graduated from Ball State University Magna Cum Laude with degrees in Directing and Theatre Education, as well as Ball State’s prestigious Academic Honors in Writing.

Read more about him and other Picture this Post writers on the Picture this Post Masthead.

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