319 Meeker St. Galena, IL 61036

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Discover the #1 Weekend Getaway in the Midwest

Our Galena Bed and Breakfast is the #1 Weekend Getaway in the MidwestAre you looking for somewhere romantic to curl up and get cozy this winter? Let us introduce you to our Galena Bed and Breakfast, considered by many to be the best weekend getaway in the Midwest. Our Bed and Breakfast is located in the charming, historic town of Galena, and only a few hours from major cities such as Chicago, Milwaukee, and Des Moines.

You might be asking what it is that makes Galena, and our Bed and Breakfast, in particular, such a delightful weekend getaway in the Midwest.  In part, it’s the many fun things to do in Galena, even in the chilly months of winter. Whether it’s getting outside for a little bit of adventure, strolling down Main Street and browsing Galena’s independent boutiques, enjoying a delicious glass of wine, beer, or spirits over laugh-filled conversations, or just enjoying the historic ambiance of this quaint town, you will be pleasantly surprised by all that Galena has to offer.

But your weekend getaway in the Midwest is about more than just the town of Galena. It’s also about the opportunity to stay in such a luxuriously elegant and historic building, and to let us take care of the details for a weekend while you do nothing but relax and enjoy the moment. When it comes to where to stay in Galena, there’s only one choice that brings you the romantic ambiance and touch of luxury that you’re looking for; Jail Hill Inn.

Our Galena Bed and Breakfast has been rated the #1 and #3 Bed and Breakfast in the country in 2019 and 2020, respectively. There are still some openings this winter, too, but you’ll need to act fast before those disappear.  Book your room at our Galena Bed and Breakfast today, and enjoy one incredible weekend getaway in the Midwest!

Our Favorite Things to do in Galena This Winter

As far as planning the best weekend getaway in the Midwest goes, you’d be hard-pressed to find a better destination than our Galena Bed and Breakfast. Whether you feel like braving the cold or would rather stick to Galena’s fun inside pursuits, there’s plenty for you to enjoy here for a weekend.

Our Galena Bed and Breakfast is the #1 Weekend Getaway in the MidwestHere are 8 fun things to do in Galena that you should consider adding to your weekend getaway in the Midwest.

  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.
  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. You can even try your hand at skijoring–a cross between cross-country skiing and dog-sledding!
  3. Take a winter hike (or snowshoe) 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.
  4. Watch eagles soar and dive for food during their annual migration along the Mississippi River at Casper Bluff Preserve and nearby Mississippi Palisades State Park. 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 TomatoesFritz and Frites, and Log Cabin Steakhouse.

Our Galena Bed and Breakfast is the #1 Weekend Getaway in the Midwest

Where to Stay for the Best Weekend Getaway in the Midwest

There’s no better way to start and end your day than at our luxury Galena Bed and Breakfast.  In the morning, you’ll wake up to a freshly prepared, gourmet, multi-course breakfast that can either be enjoyed in our socially distant dining room, or delivered at no extra charge to the privacy of your suite. 

In that breakfast, you can expect some of our freshly brewed and roasted-just-for-us coffee, freshly made juice, a fruit course to start, followed by fresh pastries, and, of course, the main dish itself, which varies frequently. 

After fueling up for the day ahead and enjoying the charms of Galena throughout the day, return to your own private oasis.  We used to host an afternoon wine and appetizer hour in our lobby every afternoon, but now we offer each guest their own private tray, packed with a delicious assortment of charcuterie, appetizers, and freshly baked cookies, along with their choice of wine from our selection.

Finally, sink into our luxury linens and comfortable beds in your spacious suite, and get ready for the best night of sleep you’ve ever had away from home.  It’s all part of what makes our Galena Bed and Breakfast the #1 weekend getaway in the Midwest.  Book your getaway now!


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Now Offering Dinner from Brazen!

We’ve partnered with our friends at the sensational Brazen Open Kitchen in Dubuque to bring you a new Friday night food delivery option!