319 Meeker St. Galena, IL 61036

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A Magical Winter Getaway in Galena

Winter Getaway in GalenaCountless couples over the years have been witness to the magical ambiance of Galena in the Winter time.  There is truly something special about it here. Glistening white snow covers the ground, old-world architecture stands stately, couples stroll hand and hand through our picturesque winter wonderland, and cozy fires are ablaze in businesses and homes around town.  Guests from all over come for skiing, snowboarding, sleigh rides, candlelit hikes, and romantic dinners.  What’s more, Galena offers an incredible range of shops, art galleries, spas, and live entertainment to fill your days and nights.  The offseason is special, and Valentine’s Day is coming up just around the corner.  The Jail Hill Inn still has some availability for the surrounding weekends, but we will soon sell out.  Book your getaway now, and see why we say you’ll always want to return, and you’ll never want to leave. 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

Experience the Holiday Season in Galena

Holiday season in Galena, IllinoisAt the Jail Hill Inn, we are busy getting ready to celebrate our first holiday season open to the public.  Next week, families will gather around their traditional holiday tables, and so begins a month-long celebration of joy and giving.  We are excited for all of the possibilities this brings us, as we get ready to celebrate with our guests. With a wide variety of shopping and holiday festivities to enjoy, there’s no better place to unwrap new holiday memories than on the charming town of Galena, Illinois.  Whether you choose to join us for some holiday shopping, dazzling light displays, time away from the chaotic stress of the holidays, or other fun holiday-themed activities, you’ll find nothing but joy and merriment in Galena throughout the upcoming holiday season. To get started on your getaway, book a room at our exquisite Bed and Breakfast today.  Continue reading

10 Ways to Enjoy a Romantic Getaway in Galena

Romantic Getaway Galena, IllinoisThese crisp, fall months practically beg for us to curl up indoors, hidden away from the harsh elements outside.  It’s the perfect time to curl up with someone special and focus on romance.  In the Midwest, there’s one romantic getaway destination that outshines the rest.  Galena, a charming small town not too far away from the Midwest’s big city centers, imbues a sense of romance around every street corner and in every restaurant and shop.  Spend your days browsing the towns historic buildings or boutique shops in downtown Galena, sipping wine at regional wineries, and taking in the magnificent scenery.  No matter how you choose to spend your time, there’s no better place to spend a romantic getaway in Galena than at our luxurious Bed and Breakfast. Continue reading

Discover the Best Bed and Breakfast in Galena

Best Galena LodgingGalena 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 fall getaway.  When searching for a place to stay, our newly renovated and award-winning Bed and Breakfast, conveniently located in downtown Galena, simply can’t be beat. Book your room today! Continue reading

5 Delicious Galena Restaurants

Romantic Getaway, enjoy Galena RestaurantsThough it’s certainly hard to believe, Labor Day is just around the corner and another summer is coming to a close in the beautiful town of Galena.  Soon, we’ll be looking for beautiful fall foliage and bracing for another winter.  But, in Galena, any time of year is a wonderful time to getaway.  Galena, located not too far from some of the Midwest’s largest cities, is the perfect place to escape from it all.  There are plenty of exciting activities to enjoy, charming stores to shop, and delicious restaurants to savor. Relax in our comfortable accommodations, and discover the best of Galena this summer. Book your room 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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Spring into Outdoor Recreation

Outdoor Recreation GalenaTwo of the most attractive aspects of Galena that draw in such large crowds are undoubtedly its ease of access, and it’s beautiful scenery.  Galena is the perfect getaway destination for a variety of people in the midwest.  It’s just one tank of gas away from many of the midwest’s large urban areas.  Despite being so close, it feels and looks distinctly different.  Galena is nestled in what is known as the Driftless Region; an area so named for the uniquely scenic landscapes left untouched during the last glacial period which flattened the remainder of the Midwest.  Instead, what was left behind were steeply rising hills and bluffs that plunge into winding river valleys.  Getting outdoors and experiencing the scenic beauty of Galena is surely one of the best parts about vacationing here.  This spring, book your room at our historic Bed and Breakfast, and discover the best of Galena’s outdoor recreation. Continue reading

Discover History in Galena

Galena History Galena is the perfect getaway destination for a variety of people in the midwest.  It’s just one tank of gas away from many of the midwest’s large urban areas, yet it feels distinctly different.  More than that, Galena is a fascinating destination with a distinctive history and an interesting variety of things to see and do.  Located in historic Jo Daviess County, Galena is the perfect place for history lovers to spend a few days.  There’s no better time to explore Galena than this spring during one of the biggest Civil War events, the annual US Grant Pilgrimage weekend.  Our historic Inn, formerly the county jail, has recently been renovated into a modern and luxurious Bed and Breakfast, making it the perfect place to end your days in Galena.  Book your room with us today so you can getaway to Galena this spring. Continue reading

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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.