319 Meeker St. Galena, IL 61036

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Galena Attractions

Our Galena Bed and Breakfast is the Perfect Fall Getaway

Fall Getaway at our Galena Bed and BreakfastSummers in Galena are filled with plenty of fun and adventure, but it’s time to start turning our attention to the upcoming fall months. With schools in or nearly in session across the country, many parents and caregivers are finding themselves thrust back into the hectic pace of day-to-day life.  So this fall, treat yourself or your loved ones to something special, and come spend a few blissful nights at our award-winning Bed and Breakfast in the historic, beautiful town of Galena.  Fall in Galena is simply magical, as the colors of the surrounding hillsides transform from green to the signature golden, fiery hues of autumn. When you stay at our luxury Galena Bed and Breakfast, you’re part of our family.  Come see what makes us different than our competitors.  Book your room at the Jail Hill Inn today. Continue reading

Explore the Galena River Trail

Galena River TrailThere are so many great things to love about the charming getaway town of Galena.  The town is home to a variety of unique shopping and attractions, delicious wineries and restaurants, and an abundance of outdoor spaces and activities to enjoy.  Better yet, most of Galena’s top attractions are located within easy walking distance from the Jail Hill Inn, making this the perfect getaway destination. In fact, one of our favorite things about Galena is the Galena River Trail, which can be accessed within minutes of leaving our Inn. From there, Galena’s beautiful countryside is yours to explore. All you need to do is book your room at the Jail Hill Inn Bed and Breakfast. Continue reading

Holiday Events and Celebrations in Galena

2017 Holiday Events in GalenaGalena’s event calendar is often packed around the holidays, and this year it’s no different.  At Jail Hill Inn, we’re gearing up for another exciting and busy holiday season, and hope you find time in your busy schedule to come visit us.  Galena is truly a magical holiday destination that you must see at least once in your lifetime.

The first of many fantastic holiday events this year starts this upcoming weekend with Galena’s 33rd Annual Nouveau Wine Weekend.  The Nouveau Wine Weekend is a celebration of the year’s harvest, and features the release of Galena Cellar’s first bottled wine of the year.   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

Spring on the Great River Road

Great River Road near GalenaIf you’ve yet to experience the incredible and unique beauty along the Great River Road, then now is the time to get here. Wanderlust Travel Magazine’s February issue has listed this spectacular destination, which passes near Galena, as one of the “Top 50 Trips” for 2017. Along the Great River Road, you can expect to see breathtaking views of the Mississippi River, majestic bluffs and landscapes, and an incredible array of birds and other inhabitants who make a living along nature’s most famous highway.  Book your room at our luxurious Galena Bed and Breakfast today, so you can come explore one of the most beautiful sections of the Great River Road near Galena this spring. Continue reading

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

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

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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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.