Not Your Mother’s Chestnut Mountain: After a recent polish, Galena’s hidden gem shines.


From the outside, the hotel looks as I remember: a rustic, familiar ski chalet. Inside is a different story, as the hotel has undergone major renovations throughout the past 3 years.

 Nine miles outside of the historical, charming, Midwest tourist mecca of Galena, IL, there’s a ski resort that you may have heard of—if you’re like me, you may even have memories of skiing there in your youth.  You probably can easily recall its name: Chestnut Mountain.

The welcoming lobby even features a piano, which a few guests were playing and singing along with when we checked out.

But if you haven’t been there lately, you really haven’t been there.

Admittedly, when I checked-in to Chestnut Mountain last week with my sister-in-law Dennae, aka my photographer, I kept my expectations in check.

I vowed to myself I wasn’t going to be a snob. I wasn’t going to cringe if my room featured shag carpeting or wood paneling.  After all, I figured, people don’t come here for deluxe lodging. They come for the action.

To my pleasant surprise, I opened the door to a spacious and modern room, graciously decorated in warm hues and featuring a killer view of the “Old Main” ski hill and Mighty Mississippi in all her frozen glory.

As I later learned, the resort has undergone major renovations within the past 3 years, and it shows!

Other things I loved about this room:

  • large enough to feature a full-sized sleeper sofa and a table and chairs in addition to the two queen beds
  • the bathroom featured two vanity sinks—one inside the bathroom, and one just outside of it
  • did I mention the killer view of the slope known as Old Main?

I have a history with Old Main. As a teenager, I collided with a middle-aged father of two on that very hill. He was minding his own business when I, at the tender age of 13, plowed into him like a run-away freight train, resulting in us both lying imbedded in the snow like two groaning snow angels.

And that was the end of my skiing career, which is why you see Lindsey Vonn on the medal stand and not me.

With that in mind, I decided to relaunch my skiing career with private lessons.

As my sister-in-law and I donned our gear, the temperature dropped suddenly from high-40’s to below freezing, and the falling rain turned our outdoor surroundings into an downhill ice rink.

God bless Dan, our instructor, he took us out and tried his best to teach us a thing or two, even though we all acknowledged and agreed the conditions were completely terrible, and this was a very bad idea.

Within 5 minutes, my ski partner was on the ground and decided to opt out.  Dan and I powered through for an abbreviated lesson, which included two trips down the bunny hill and covered stopping and turning—two very essential things that eluded me 26 years ago.

Unfortunately, that is where the rebirth of my skiing career ended, as Mother Nature decided it was not the right day for me to relaunch my skiing career after all.  I’m guessing Ms. Vonn paid her off.

Even though my skiing dreams were cut short, I learned a few things through the process:

The staff, though young, is exceedingly friendly, informative and helpful.  From rental to hillside, I always felt like they were ready to guide me through using the equipment and navigating the place.

Like Ron Burgundy, Chestnut Mountain is a pretty big deal, even to people far away.  Hundreds of ski boots were already lined up on tables for the following morning.  Thankfully, the conditions were much improved  the next day, and 500 guests showed up before we checked out, which included 5 charter buses, give or take, from Iowa City. The day before we checked in, the Special Olympics held trials at Chestnut.

Their Ski Shop was all kinds of awesome.  Seriously, if you were need of winter gear or apparel, you could walk out of that place in style and ready for action.

Moon Boot Sale!!!

A little tip: Look for weekday, Friday night and Sunday afternoon specials on Chestnut’s website if you’re needing to enjoy the slopes on a budget. And while I highly recommend the private lessons (at $50/hour), group lessons are a budget-friendly alternative as well. They also have youth-oriented programs, like Powder Pups, where kids can learn alongside other kids their age.

Chestnut is a popular destination for skiers and snowboarders alike!

Other Amenities & Features:

Onsite dining:

Chestnut offers three options with varying price points:

$5-10: Mountain Top Café: One employee referred to it as the cafeteria. We didn’t get a chance to dine there, but sounds like a convenient place for soups, sandwiches, pizza and burgers that’s easily accessible to skiers.

$8-15: Summit Sports Bar: Upscale, casual sports bar and grill with breathtaking views, a chillaxed atmosphere and a nice variety of drinks and platters. I recommend the chicken sandwich! They also offer plenty of breakfast options and a breakfast buffet when guest count is high enough.


Summit Sports Bar

$20 & up: Sunset Grille: A upscale restaurant that will appease every type of taste bud.  While the dining room itself was closed during our visit, we were able to order from the Sunset’s menu for dinner. My walnut-encrusted walleye was delicious with a perfectly crunchy exterior to compliment the tender, flaky fish. Oh, and it was impressively HUGE. Seriously the largest fish I’ve ever seen on a plate!

Indoor Pool and Hot Tub:


I was hoping to take a dip in their hot tub, but it remained pretty full during our visit, due to the uncooperative weather conditions.  Still, a great place for kids and adults to unwind indoors. We popped in for some photos just before checking out and found the place serenely empty.

Warm Weather Activities:

The folks at Chestnut have done a stellar job developing a full menu of distinct and diverse activities for visitors once the snow melts.  I visited a few years back with my son for an afternoon, and I’d love to return to actually stay onsite and take full advantage of their summer offerings, which include:

The Alpine Slide: My son enjoyed the thrill of racing me down the hill; I enjoyed the scenic ride back up on the ski lift.

The Soaring Eagle Zipline: This just made us both SO HAPPY we had to go twice.

Segway tours: I’ve never been on a Segway, but I so badly want to come back to Chestnut and try this.

River Cruises: These relaxed, 1.5 hour cruises in a large pontoon boat are a great way to take in the scenery and wildlife along the Mississippi.

Also mini golf, disc golf and bicycle rental are available onsite.

Parting Thoughts:

While Chestnut Mountain Resort’s outdoor activities are a draw in and of themselves, I would not hesitate to recommend the hotel as an affordable and breathtakingly scenic alternative to staying in town. With the recent renovations, the great value of the rooms (starting at $99), the indoor pool, dining options and unbeatable views, Chestnut Mountain has plenty of appeal for any guest.

One Reply to “Not Your Mother’s Chestnut Mountain: After a recent polish, Galena’s hidden gem shines.”

  1. Wow what great memories while growing up! Love the place and my favorite are the Alpine slides! I’m glad they keep it fresh! Lynda

Comments are closed.