Chestnut Mountain Resort, Galena, IL

Chestnut Mountain Resort lodge

I was super excited to be invited on a media visit to Chestnut Mountain Resort – this is a Midwest destination that has long been on my radar. For years I’ve planned the drive (3 to 3 1/2 hours from downtown Chicago), but it’s never come together. Still, this area overlooking the Mississippi River is one of the most beautiful in Illinois, so I knew it was only a matter of time.


Driving up, one is struck by the European style of the main building, somewhat a surprise in this bucolic countryside, where pole barns and farm houses are the more normal architectural styles seen hereabouts. The lodge is a commanding presence, making one feel as if you’ve arrived somewhere special.

General lodge slideshow:

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That feeling is blunted a bit upon entry – while obviously updated at some point, the lodge feels a bit stale. Everything is clean and orderly, it just doesn’t feel new or up-to-the moment. The staff is very friendly and, for the most part, seem to do their jobs pretty well.


If you can, opt for one of the slopeside rooms that face the Mississippi River, that is a helluva view. The resort put me up in a double room that overlooked the beginners’ run with a view downslope to one of the greatest of rivers, the Mississippi.

Again, as in the lobby, the room seemed clean and habitable, but not new or modern. Vanities outside the bathroom just don’t feel right to me. Add in a television channel list of only 25 channels (many of which didn’t work), and it kind of gives the feeling of a cheap motel.

This feeling was heightened by the discovery of a pair of girls socks between the loveseat and the windows – I had just entered the room and no girl was with me, so not a great find at all.

General room slideshow:

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That being said, the bed was very comfortable, the view with my takeout dinner from the bar was outstanding, and I’d happily stay there again (as long as the socks had been removed).


The Summit, The Sunset Grille, and The Mountain Top Café make up the dining options at the resort. For dinner, I opted to get food for takeout from The Summit, which is the bar – oddly enough, they don’t deliver. Simple enough: order, pay, food is made, dinner is had back at the room. Very yummy. I can vouch for the chicken wings, hamburger, and onion wings, and was pleasantly surprised by their modest yet careful wine list.

I ate at the Sunset Grille the following morning, and the views from the windows were breathtaking, definitely sit there if it’s at all an option. Service was decent, though not sprightly, in my opinion (I’d hire only morning people to serve breakfast). The dining room was pretty typical Midwest resort, and could use an update in design. What really needs work is the food. While decent tasting, it has the unmistakeable feel of  an Aramark or Sysco, reasonable food but not inspiring.

Dining slideshow:

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The Mountain Top Café is at slope level, so I visited there several times while skiing, once to use the bathrooms and another to get some lunch. Chestnut can take some cues from more established resorts and add items like helmet shelves and glove baskets in the bathrooms to make it easier to get one’s business done while schlepping lotso gear. The food here is also typical Midwest resort grub, but the prices are on the high side for quality. I will say the entire experience was saved by one of their homemade chocolate chip cookies – if the rest of the food was up to that standard, this would be a great place to eat.

If it sounds like I’m down on the resort, it’s not the case at all. I just want them to live up to their reputation and what I think it could be with some money and a higher bar set.


Winter is for skiing and snowboarding, snowshoeing, or just getting out on the trails. Make sure to walk along the north side of the lodge and take the path out to overlook, with a majestic tree framing amazing views over the Mississippi River and beyond.

Summer gives one a chance to try out the Alpine Slide, ride the bike path, hike trails, and enjoy scenic views over the Mississippi River. If that’s not enough, guests can enjoy the Soaring Eagle Zip Line, miniature golf, disc golf, or Segway tours.

At any time of year, check out the indoor pool, hot tub and sauna, the game room, or utilize their meeting spaces for work or pleasure.

Amenities slideshow:

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Overall, this is a really nice getaway, close to Chicago as well as the folks who live in the area and across the River in Iowa. Everything is decent or better at the resort, with things like views on the extraordinary side. Definitely worth a visit.

Updating the resort to a more modern standard would make it a must-see, but only if the food was brought up to higher standards as well. My criticism is more in the vein of pushing them to get better than finding things actually wrong – my guess is most guests don’t even notice.

I know my family would love to visit here and we’d have a great time; now I just need to decide if we’ll come next for a Summer or a Winter vacation.

Directions to Chestnut Mountain Resort:

*Lodging and some dining were provided by the resort for editorial purposes – all opinions are my own.

Nearby destinations:


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