319 Meeker St. Galena, IL 61036


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10 Things You Simply Must do in Galena This Winter

10 Things to do in Galena This WinterHave you ever visited Galena during the winter? It’s a wonderful place to visit, even when there’s snow on the ground!  There are plenty of delightful things to do this winter, and we have a great guide for you. Head out on a cross country skiing adventure, explore our vibrant and historic downtown, or sit back and savor the luxurious accommodations found at our Galena Bed and Breakfast.

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. Your day will start with a delicious breakfast, but that definitely isn’t the end of our award-winning hospitality.  In the afternoon, join us for a delicious wine and cheese hour, along with some delicious fresh cookies, hot from the oven. Come see it for yourself, and book a room at our Galena Bed and Breakfast today.

10 Things to do in Galena This Winter

We absolutely love Galena during the summer. There’s so much to do, and the town buzzes with excitement. During the fall, Mother Nature paints the surrounding hills with extraordinary colors. Despite all of this, 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!

10 Things to do in Galena This WinterGet in on the fun this year!  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 it has 19 total ski runs and a 7-acre terrain park suitable for a variety of experience levels. Chestnut Mountain will also be the host of the Special Olympics Illinois in February.
  2. Head to the Nordic Center at Eagle Ridge Resort an 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. Take 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. Enjoy the scenic trails with one of the most classic winter activities of them all; a horse-drawn sleigh ride.  The Shenandoah Riding Center offers hour-long trips through the scenic winter wonderland of Galena.
  6. If you want a little respite from the cold outdoors, head to the local wineries, which are open for tastings year-round.  You can’t go wrong with a visit to award-winning Galena Cellars or Massbach Ridge Winery, both with tasting rooms conveniently located in downtown Galena.
  7. Meander through 19th-century charm all dressed up for the holidays.  Downtown Galena is a fun place to browse any time of year, but there’s no time more magical than this winter when it’s all dressed up for the holidays.
  8. 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.
  9. Pamper yourself with an in-room massage in the comfort of your suite at Jail Hill Inn.
  10. Hit up one of Galena’s fun winter events, such as the popular Winter Carnival Weekend in February 2020, or the Galena Whiskey Weekend, which starts on January 25, 2020.

The Best Galena Bed and Breakfast

10 Things to do in Galena This WinterJail Hill Inn, rated the #1 Bed and Breakfast in the country, invites you to sink into our luxurious accommodations this winter. From the moment you step through our door, you’ll 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.

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. Book your room at our romantic Galena Bed and Breakfast today!


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