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Add Luxury to Your Ski Weekends This Winter

You may not realize it yet, but a winter getaway to Galena, Illinois, offers the perfect blend of outdoor adventure and small-town charm – and when you stay at our Galena Bed and Breakfast, a bit of much-deserved luxury. If you’re looking to hit the slopes, Galena skiing is at its best at Chestnut Mountain Resort. With 19 ski trails that overlook the Mississippi River, it’s an ideal spot for both seasoned skiers and beginners. Whether you’re on the slopes or simply enjoying the winter landscape, Chestnut Mountain is the go-to destination for winter fun in Galena.

Winter in Galena isn’t just about skiing. The town transforms into a winter wonderland, with its historic streets lined with charming shops, cozy cafés, and local restaurants perfect for warming up after a day in the snow. You can enjoy a quiet walk through the downtown, window shopping as you go, or head out to the Eagle Ridge Resort for a bit of snowshoeing, sledding, and more. For something more relaxing, check out the local wineries, where you can sip on regional wines in charming downtown settings.

Whether you’ve spent your day in Galena skiing or enjoying something else, there’s no better place to wind down your day than our luxury Galena Bed and Breakfast. If you want to add a bit of luxury to your getaways, Jail Hill Inn offers the ultimate retreat. With exceptional hospitality, luxurious accommodations, and high-end amenities that perfectly blend Galena’s historic charm with modern comforts, this is the place to stay. Ski and play your way through winter, but leave the relaxing to us. Book your stay at our #1-rated Galena Bed and Breakfast today!

Galena Skiing at Chestnut Mountain Resort

Galena Skiing at Chestnut Mountain Resort

When it comes time for Galena skiing this winter, you’ll be happy to learn that Chestnut Mountain Resort is one of the Midwest’s best-kept secrets. Located just outside Galena, the resort offers 19 runs perfect for Galena skiing and snowboarding. These runs cater to all levels, from easy bunny slopes to expert black diamond runs. The total vertical drop here is 475 feet, which makes for an excellent day on the slopes for a wide range of skiers.

While the opportunity to enjoy some Galena skiing and snowboarding is certainly the primary reason to visit Chesnut Mountain Resort, the resort’s location on the banks of the Mississippi River sets it apart from other regional ski spots. As you stand at the top of the runs and get ready to make your descent, it’s impossible not to admire the stunning river views.

In addition to these gorgeous views and varied terrain, the relaxed pace you’ll find here makes Galena skiing a great alternative to more crowded winter destinations. While larger ski resorts often mean long lift lines and packed lodges, Galena offers a more laid-back experience without sacrificing quality. When you’re done skiing for the day, you’re welcome to sit back and relax in the resort’s restaurants or make the short drive back into downtown Galena and enjoy a little aprés ski. 

Galena’s downtown is a short drive from Chestnut Mountain Resort, which means you can go from an afternoon of Galena skiing to an evening of small-town charm in no time. Galena’s charming downtown is filled with unique shops, local restaurants, and even a few cozy spots to grab a post-ski drink. Whether you’re planning a trip with friends or a romantic weekend away, Galena skiing at Chestnut Mountain is an inviting choice for a relaxed yet adventurous winter escape.

Winter on the Galena River Trail - where you'll find plenty of things to do in Galena, IL this winter

More Things to Do in Galena, IL, This Winter

Galena skiing is, of course, just one of the many things to do in Galena, IL, this winter. You’ll be charmed by Galena’s scenic winter landscapes everywhere you turn. There are plenty of places beyond Chesnut Mountain Resort to explore if playing outside is on your to-do list this winter, but if you’d prefer to get cozy and pampered far away from the harsh winter elements, we can help with that, too. Our Galena Bed and Breakfast is perfect for cozy, pampered, and indulgent weekends away with your sweetheart! 

Whether your idea of winter fun is enjoying a bit of Galena skiing or soothing your muscles with a relaxing massage, you’ll find plenty of diverse things to do in Galena, IL, this winter. We’ve listed a few of our favorites below! 

  1. If you’re here for some Galena skiing and want to have a little more playtime in the snow, head to the Nordic Center at Eagle Ridge Resort. It’s one of the leading things to do in Galena, IL, in the winter. 
  2. You can also enjoy gorgeous winter hikes at our local preserves, such as Casper Bluff PreserveBuehler Preserve, Horseshoe Mound, and the Galena River Trail.
  3. Just as winter is perfect for Galena skiing, it’s also the season for eagle-watching. The best place to watch these majestic birds soar is Mississippi Palisades State Park. The peak migration season is mid-January through February. 
  4. Enjoy local wine tasting at Galena Cellars and Massbach Ridge Winery, or celebrate with a glass of bubbly at Champagne on Main
  5. Experience luxury at our Galena Bed and Breakfast with a single or couples massage in our brand-new spa room. For more advanced treatments like facials, enjoy services at one of these fantastic local Galena Day Spas
  6. Head into downtown Galena for some shopping this winter. With over 100 independently owned shops, there’s something for everyone!
  7. Don’t forget to enjoy plenty of fantastic meals at the top Galena Restaurants.

As you can see, there are plenty of things to do in Galena, IL, this winter. Winter getaways are just a few clicks away. Book your room at our top-rated Galena Bed and Breakfast today! 

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