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The Best of the Best in Galena

Enjoy a Magical Christmas in Galena, IL in 2023!

When guests ask us which room at our Galena, IL Bed and Breakfast is our favorite, our answer is, “All of them!” Similarly, when asked what our favorite season is, the answer is, “All of them!” That said, there is something special about cozy winter getaways during Christmas in Galena. 

There are, of course, plenty of things to do in Galena, Illinois, no matter the season. From excellent holiday shopping and fantastic events in downtown Galena to thrilling skiing at Chestnut Mountain Resort, you can have some fun here during the winter in Galena. If you’re looking for a touch more pampering and luxury, we can take care of that, too! 

Christmas in Galena is a beautiful time of year to visit our Galena, IL Bed and Breakfast. No surface goes uncovered by our magical and stunning decorations. We shut down for a few days around Thanksgiving every year and open up on Black Friday, all decked out in our Christmas glory. Beyond just being beautiful and festive, though, our Galena, IL Bed and Breakfast offers just the right combination of indulgent pampering and casual elegance. 

Whether you want to start your holiday shopping or you’re looking for a quiet retreat amid this busier-than-ever season, we’d love to host you. We’d also welcome you with open arms after the festivities are over, as we leave our decorations up until January 15! There’s never been a better time to experience the magic of Christmas in Galena. Book your room at our #1-rated Best Galena, IL Bed and Breakfast today! 

A Jail Hill Inn ornament and decorations - the best romantic getaway in Galena, IL and a great place to celebrate Christmas in Galena, IL

Best Place to Celebrate Christmas in Galena, IL

As we’ve said, there are plenty of things to do in Galena, IL this winter. Even if all you want to do is relax and enjoy some quiet time, there’s plenty to look at and admire during Christmas in Galena. The town is a charming, festive, and historic place to retreat this winter – and when you stay at our Galena, IL Bed and Breakfast, you’ll find all the time and space you need to enjoy the quiet respite you’re craving. 

Venture into downtown Galena and enjoy shopping at the 100+ boutiques that line Main Street. Many are decorated and bring holiday cheer to all who wander into their shops. Of course, beyond shopping, there are plenty of great events celebrating Christmas in Galena, too. On November 25, Galena will start celebrating the season with the annual Galena Holiday Kickoff. After that, there are several great events celebrating Christmas in Galena, including those we’ve listed below. 

  1. Celebrate Christmas in Galena with the annual Galena Holidaze Festival featuring local artisans, food, live music, and general seasonal merriment. 
  2. One of the most celebrated events during Christmas in Galena is the annual Holiday Fire in the Sky – a spectacular fireworks show you can enjoy in the brisk and chilly outdoors or from the cozy picture windows at our Galena, IL Bed and Breakfast!
  3. Perhaps the most popular event during Christmas in Galena is the Night of the Luminaria and Living Windows. The entire town transforms into a magical, glowy winter wonderland you must see at least once. 
  4. Enjoy an old-fashioned Christmas at the Fort – a historic celebration of Christmas past at the Apple River Fort.
  5. Tour Galena’s beautiful Bed and Breakfasts – including our own Galena, IL Bed and Breakfast – all dressed up for the season during the annual Mistletoe Stroll Tour of  Holiday Houses
  6. Warm up and have some fun during downtown Galena’s Snowflakes and Sweets Stroll – another excellent opportunity for some holiday shopping! 
  7. Though not technically in Galena, don’t miss the nearby Stockton Festival of Lights. Another great event in Stockton is the annual Stockton Christmas Walk
  8. Another great location celebration is Christmas in Elizabeth – a great time to browse the shops in our historic neighboring town. 

Each of these events provides a wonderful way to celebrate Christmas in Galena – but we also know many of our guests are looking for a cozy, quiet place to relax and enjoy some quality downtime. There’s no better place for that than our #1-rated Galena, IL Bed and Breakfast. There’s no Galena lodging that compares to Jail Hill Inn – but you don’t just have to take our word for it. Our 600+ all 5-star reviews speak volumes – and we’d love to share the experience with you this winter.

Snow covered tracks in Galena - a beautiful place to celebrate christmas in Galena, IL

7 More Things to Do in Galena This Winter

If you’re celebrating Christmas in Galena in style with these fun events and staying at our Galena, IL Bed and Breakfast, then perhaps you’re looking for more things to do this winter. Luckily, there are plenty of things to do in Galena in the winter – and that’s one of the many things we love about this charming midwestern town. There’s always something to do, no matter the time of year! 

Whether browsing the shops in downtown Galena or getting outside to enjoy some snowsports, we’d love to share the best of winter in Galena with you this year. Many of these things can also be enjoyed well after the holidays when things have settled down and the crowds have returned home. 

Of course, we also recognize that winter is the perfect season to stay indoors and get cozy with your sweetheart. There’s no place more suited for those romantic moments than our luxurious Galena, IL Bed and Breakfast. For those few moments when you want to get outside, here are some of our favorite things to do in Galena, Illinois in the winter.

  1. Of all the things to do in Galena, IL in the winter, visits to Chestnut Mountain Resort are at the top. This small but charming resort offers 19 ski runs and gorgeous views of the Mississippi River, and it’s only a short drive from our Galena, IL Bed and Breakfast. Even if you don’t enjoy skiing, lunch or dinner at their restaurant overlooking the slopes and river below is certainly worth it!
  2. If you don’t enjoy the adrenaline rush from downhill skiing, perhaps cross-country skiing or snowshoeing at Nordic Center at Eagle Ridge Resort is more your speed? They also offer ice skating and sledding – a one-stop destination for some of the best things to do in Galena, IL in the winter! 
  3. You can also simply enjoy a quiet walk through Galena’s winter wonderland at surrounding nature preserves like Casper Bluff Preserve and Buehler Preserve.
  4. Take in some of the wintry views from the Galena River Trail, which you can easily reach from our Galena, IL  Bed and Breakfast. 
  5. After the busy rush of Christmas in Galena, retreat to our tranquil Galena, IL Bed and Breakfast and enjoy the annual eagle migration at Mississippi Palisades State Park. They move through the area between mid-January through February.
  6. When you’re ready to warm up after a chilly day enjoying Galena’s winter wonderland, sip and swirl your way through delicious local wines at Galena Cellars and Massbach Ridge Winery, both of which feature tasting rooms in downtown Galena. 
  7. No trip to Galena would be complete without delicious meals at the Best Galena restaurants – most of which are within easy walking distance of our Galena, IL Bed and Breakfast.

There’s nothing more magical than a getaway to Galena this winter, particularly when you stay at our Galena, IL Bed and Breakfast. Book your room today and enjoy the best of Christmas in Galena with us this winter!

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Give The Gift of Jail Hill Inn This Christmas

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