From Our Blog

The Best of the Best in Galena

8 Things You Simply Must do in Galena This Winter

There’s no shortage of exciting things to do in Galena in the winter.  It’s a wonderful place to visit, even when there’s snow on the ground. In fact, it gets a little more magical when blanketed with white, powdery snow.  Whether you’re looking for a bit of outdoor fun on skis or snowshoes, would prefer to explore the vibrant and historic downtown, or would rather just sit back and relax in luxurious comfort at Jail Hill Inn, we’d love to share all the best things to do in Galena this winter with you.

Galena has long been a popular getaway destination for those living in or around the Chicago area, and these winter months should be no different. Even if you don’t love spending time outside during the winter, the chance to stay at our romantic Inn is more than worth the time it takes to get here. Book a room at our Galena Bed and Breakfast today.

A young couple enjoying the best things to do in Galena This Winter

10 Things to do in Galena This Winter

We absolutely love Galena during the summer. There are so many things to do in Galena at that time of year, and the town positively buzzes with excitement. During the fall, Mother Nature paints the surrounding hills with extraordinary colors.

Even so, we think you’d be missing out on something special if you didn’t come to stay with us in Galena this winter. Galena is a surprising yet wonderful year-round getaway destination, and it’s absolutely perfect for the snow bunnies out there! Here are 10 fun things to do in Galena that we think you might like to try next time you stay with us at the Jail Hill Inn:

  1. If you’re looking for a fun and easy skiing or snowboarding getaway, consider visiting us and spending a day or two on the slopes at Chestnut Mountain Resort. It’s one of the best ski destinations in the Midwest, and certainly one of our favorite things to do in Galena in the winter.  There are 19 total ski runs and a 7-acre terrain park suitable for a variety of experience levels.
  2. Head to the Nordic Center at Eagle Ridge Resort and enjoy an authentic outdoor ice skating experience on their 1.5-mile long pond.  They also have several miles of groomed cross country and snowshoeing trails, and of course sledding.  You can even try your hand at skijoring–a cross between cross-country skiing and dog-sledding!
  3. One of the most beautiful things to do in Galena this winter is to enjoy a winter hike through Casper Bluff Preserve or just enjoy the quiet serenity of nature at Galena’s many nature preserves.  Favorites places for winter hiking include Buehler Preserve and the Galena River Trail. If it’s snowing outside, try exploring these areas on snowshoes.
  4. Watch eagles soar and dive for food during their annual migration along the Mississippi River.  Casper Bluff Preserve and nearby Mississippi Palisades State Park are both excellent locations to spot these graceful birds, and peak times to see them are mid-January through February.
  5. There are just as many great things to do in Galena indoors.  Spend a day wine tasting at local wineries, which are open for tastings year-round. Galena Cellars and Massbach Ridge Winery both have tasting rooms conveniently located in downtown Galena.
  6. Romantic dinners for two are the perfect way to end any day in Galena, regardless of the type of winter activities you chose to indulge in.  Favorite restaurants are Fried Green Tomatoes, Fritz and Frites, and Log Cabin Steakhouse.
  7. Hit up one of Galena’s fun winter events, such as the popular Winter Carnival Weekend or the Galena Whiskey Weekend – there really are always fun things to do in Galena!

Getting cozy at our Galena Bed and Breakfast is one of the best things to do in Galena This Winter

Unwind at our #1 Best Galena Bed and Breakfast

While there are so many wonderful things to do in Galena this winter, it’s also a delightful season to sit back, relax, and enjoy a bit of quality downtime. Jail Hill Inn is the best Bed and Breakfast in Galena, offering six luxurious and inviting guest rooms.  You’ll be hard-pressed to find a more inviting place to sink into this winter, or really, any time of year.

From the moment you step through our door, you’ll be sure to feel at home in our elegant bed and breakfast. Whatever it is that draws you into Galena this winter, you’ll see in an instant why our luxurious and spacious guest rooms make for the perfect winter getaway. Each morning, we’ll treat you to a sensational three-course breakfast, and in the afternoon we’ll treat you to a sumptuous selection of wine, charcuterie, and house-made appetizers.

A day or two spent with us will melt every ounce of the stress you’re feeling away. Come experience the magic of Galena this winter and enjoy as many – or as few – of these things to do in Galena. Book your room at our #1-rated Galena Bed and Breakfast today!

Scroll to Top

Give The Gift of Jail Hill Inn This Christmas

Give your loved one a very special gift of a stay at Jail Hill Inn .  We offer gift certificates in many amounts.