319 Meeker St. Galena, IL 61036

815-777-3000

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Chestnut Mountain Resort

10 Instagram Photos to Take of Galena This Fall

Instagram Worthy Photos to Take When you Visit our Bed and Breakfast in GalenaThough many of us may not want to admit it, we love to capure picture-perfect moments of our vacations to share on Instagram. It helps when you have an exceptionally beautiful place to photograph! If you’ve ever visited Galena in the fall, then you know just how extraordinarily beautiful this historic little town is. If this will be your first time, you’re in for a treat. The hillsides around Galena light up in their fiery shades of fall each September and October, making for a breathtaking display that must be experienced to be believed.  Galena, located within easy driving distance from Chicago, Minneapolis, Des Moines, and St. Louis, is the perfect getaway destination this fall. Between hiking through the beautiful fall colors and soaking up the small-town charm of downtown Galena, there are a number of Instagram worthy destinations to show off during your stay in picturesque Galena.  Book your room at the Jail Hill Inn, and enjoy another spectacular fall at the country’s #1-rated Bed and Breakfast. Continue reading

10 Ridiculously Fun Things To Do in Galena in 2019

10 Things to do in Galena in 2019Are you looking for a fun getaway destination? Look no further!  We love our little town of Galena and have some great ideas for all the fun things to do in galena this year, topped off, of course, with a stay at our luxury Bed and Breakfast.

It’s hard to believe sometimes, but after just over 3 years in business, Jail Hill Inn has seen incredible success.  We were named Business of the Year by the Galena Chamber of Commerce, we earned a near-perfect score from Select Registry, and perhaps better yet, TripAdvisor named us the #1 Bed and Breakfast in the United States, and the #2 Bed and Breakfast in the world. Those are all incredible honors, and it has earned us quite a bit of positive press in local and regional media outlets. We’re so grateful for all of our guests over the years that have made this possible, and who continue to stay with us at our Galena Bed and Breakfast. We truly wouldn’t be here without you!  But, that also means we’re seeing a lot of recent reservations, and rooms are booking up quickly both now and into the summer and fall of 2019, especially on those busy and coveted weekends.  If you want to get away to Jail Hill Inn in 2019, you should consider booking your getaways now, and taking advantage of our availability while we still have it. Continue reading

Where to Find Fall Foliage in Galena

Galena During Peak Fall FoliageNow that Labor Day Weekend has passed, we can officially, though reluctantly, say goodbye to summer, and welcome the fast-approaching fall season. The hillsides above Galena are already showing hints of their colorful autumnal hues, which means now is the perfect time to plan a getaway to Galena.  As the air begins to cool, we’ll soon be surrounded by fall’s hallmark hues of crimson, orange, yellow, and green. You won’t have to go far to see the finest fall foliage the Midwest has to offer.  We have a few great ideas to make this fall foliage season one you’ll never forget. But first, you need to book your room at our luxury Galena Bed and Breakfast. Rooms will fill up fast during peak fall foliage season, so don’t wait! Continue reading

Indulge in Luxury at Galena’s Jail Hill Inn

indulge in luxury at Jail Hill Inn in galenaGalena is a charming tourist destination loved by many.  It is conveniently located not too far from some of the Midwest’s largest cities, and is the perfect place to escape for a few quiet days in the country. Expect your days to be filled with exploring the beautiful outdoors, browsing the charming stores, and relaxing over a delicious meal at Galena’s best restaurants.  The charm of this small town has the makings of a spectacular winter getaway, right when our Inn is at its coziest.  When searching for a place to stay, our beautifully renovated and award-winning luxury Bed and Breakfast simply can’t be beat. Book your room today! Continue reading

Come See the Fall Foliage in Galena

Fall Foliage in Galena, IllinoisNow that Labor Day Weekend has passed, we can officially, though reluctantly, say goodbye to summer, and welcome the fast-approaching fall. The hillsides above Galena are already showing hints of their colorful autumnal hues, which means now is the perfect time to plan a getaway to Galena.  As the air begins to cool, we’ll soon be surrounded by fall’s hallmark hues of crimson, orange, yellow, and green. You won’t have to go far to see the finest fall foliage the Midwest has to offer.  Take advantage of this incredible fall weather, and book your room with us today. Continue reading

Summer at Chestnut Mountain Resort

Chestnut Mountain Adventures Near Galena, IllinoisThe quaint town of Galena is one of the top getaway destinations in the Midwest.  It’s a short drive away from major cities like Chicago and Milwaukee, and it offers plenty to see and do for a variety of travelers.  Galena’s charm, which brings back guests for repeated visits over the years, stems from it’s historic feel.  It’s as if the town was frozen somewhere in the 1800’s.  With that historically charming feel though, comes a town fit for modern travelers.  Here, you’ll find fun tours, picturesque scenery, lots of outdoor recreation at places like Chestnut Mountain Resort, breweries, distilleries, and wineries, and incredible shopping along Downtown Galena’s Main Street.  Step back in time with us and experience the magic of Galena this summer.  Book your room at our recently renovated and luxurious Bed and Breakfast, currently rated as the best lodging property in all of Galena.   Continue reading

Hit the Trails Around Galena

Hiking and Biking Trails in GalenaAs we officially sail into summer in just a few days, it’s time to start making plans to enjoy the warm summer sun.  There’s no better place to do this than the charming, historic town of Galena.  Our historic Main Street is nestled along the scenic Galena River, and surrounded by the rolling hills pervasive in this region of Illinois.  Plan a getaway to our luxury Bed and Breakfast, and you’ll be situated just steps from all downtown Galena has to offer.  From the moment you step through our doors at the Jail Hill Inn, it’s time to embrace a simpler time.  The picturesque countryside will beckon you into the great outdoors.  Galena is home to many great hiking and biking trails just waiting to be discovered.  Book your room at our Galena Bed and Breakfast today. Continue reading

Winter Activities to Enjoy in Galena

Winter Activities to Enjoy in Galena, IllinoisWhether you’re looking for a little outdoor recreation, or the perfect excuse to curl up and get cozy with the one you love, there are plenty of reasons to visit Galena this winter.  During the snowy winter months, Galena transforms into a picturesque wonderland, complete with snow-covered hills and valleys and charming old-world architecture.  Winter activities are plentiful in Galena, ranging from skiing, snowboarding, and sleigh rides, to candlelit hikes and romantic dinners.  With far less crowds than the rest of the year, winter is arguably one of the best times to plan a getaway to our luxurious Bed and Breakfast in downtown Galena.  Book your stay with us today! Continue reading

Plan the Best Romantic Getaway This Summer

Romantic Getaway Galena, IllinoisWhen people in the Midwest look for a romantic getaway destination, Galena is often the go-to place. Couples all across the Midwest are discovering Galena’s small town, romantic charm.  There is no doubt that love is in the air in Galena, a town practically built for the romantic in all of us. Galena is easily accessible, too, considered a “one-tank” getaway destination from several major cities, including Chicago & Milwaukee.  Book your room at our newly renovated, luxury Bed and Breakfast, and experience the romance of Galena this summer.

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5 Summer Activities to Enjoy in Galena

Summer Activities GalenaAnother warm and adventurous summer is knocking on our door, marking the time of year when everyone seems ready to get outside. For years, the charming town Galena has been winning awards for being one of the best small towns in America. To us, this comes as no surprise.  Galena is a region marked by its gorgeous rolling and rugged terrain, known for unbeatable opportunities for outdoor adventure. Here, you’ll find a rich sense of history, plenty of land and water trails to explore and an incredible variety of other fun summer activities to choose from.  Located just a few short hours from many major metropolitan areas, there truly is no better place to be this summer than Galena.  Book your room at our historic Bed and Breakfast, and experience the charming spirit of this small town firsthand.

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Jail Hill Inn Bed and Breakfast in Galena Wins Top TripAdvisor Award

Jail Hill Inn has been named the #1 Bed and Breakfast in the United States and #2 in the world by TripAdvisor.