319 Meeker St. Galena, IL 61036

815-777-3000

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Chestnut Mountain Resort

The 10 BEST Things to do in Galena This Fall

10 of the BEST Things to do in Galena This Fall Near our Bed and BreakfastThings often look different in Galena from year to year, with new attractions, events, shops, restaurants, and other things added to our list each year. This year, mostly thanks to the COVID-19 Pandemic, things are definitely different in Galena.  Even so, it’s still one of the best weekend getaways from Chicago, and there are plenty of wonderful things to do in Galena this fall.  While many of our favorite fall events have been canceled in 2020, we have some ideas to ensure you have a fun and memorable getaway.

At the heart of your stay in Galena, you’ll still find the same exceptional accommodations offered by Jail Hill Inn, Galena’s #1 rated Bed and Breakfast. The experience of staying with us hasn’t changed too much, but there are a couple of notable adjustments. Breakfast does look a little different, in that we’re offering two choices: You can still enjoy us in the socially-distanced dining room downstairs, or you can request breakfast be brought directly to your suite.  And, in the afternoon, rather than hosting an afternoon wine and cheese reception, we’re delivering hand-crafted trays with your own personalized selection of wine and a delicious assortment of charcuterie, appetizers, and cookies for you to munch on at your leisure.

One thing that hasn’t changed at Jail Hill Inn is our absolute dedication to hospitality, where every detail of your stay is carefully attended to.  This fall, come celebrate the changing of the seasons with us.  Discover new things to do in Galena this fall, and leave with unforgettable memories and plans to return again.  Book your room at our Bed and Breakfast in Galena today! Continue reading

Scenic Drives Around Galena, IL

Fall Scenic Drives Near our Galena Bed and BreakfastFall is a breathtakingly beautiful time of year to be in Galena.  One of our favorite ways to enjoy fall in Galena, IL is to take scenic drives, of which there are plenty near our Bed and Breakfast. The winding country roads are absolutely perfect for these scenic drives, too!  Fall’s seasonal display of color paints the hills around Galena, bringing this area to life in new and exciting ways.

Making yourself at home at our luxurious Galena Bed and Breakfast is the perfect recipe for a memorable and exciting vacation.  We take the meaning of hospitality to a new level, and, most importantly, are dedicated to keeping travelers safe during these unprecedented times. If you’ve never experienced fall in Galena before, this year provides you with the perfect opportunity.

Not only is it a beautiful place to relax and unwind, but it’s a safe and comfortable place to get away for that much-needed change of scenery.  Book your room at our Galena Bed and Breakfast today! Continue reading

10 Socially Distanced Things to do in Galena This Summer

10 Socially Distanced Things to do in GalenaWe know many of you are longing to get out of your house and put this global pandemic behind you, but you’re also probably unsure of just what your future travels are going to look like.  We don’t have all of the answers, but we do have some ideas for things to do in Galena this summer that help us maintain social distancing as it’s needed.  Tourism is one of the most important parts of Galena’s economy, and we’re anxious to open our doors and welcome guests back to Jail Hill Inn.  It’s the same for all of the restaurants, shops, and small businesses that make up the fabric of everyday life here in Galena.

More than anything else, we’ve missed being your special place; a place where you can get away and relax.  We think short getaways are important to our collective mental health and wellbeing.  That’s why we’re working hard on our end to ensure you have a clean and safe place to visit, and why we’re coming up with ideas for socially distant things to do in Galena that our guests can count on!

After these many weeks of social isolation, don’t you think it would be nice to plan in some “you” time and to have something to look forward to this summer and fall?  There’s no doubt that our Galena Bed and Breakfast, still rated the #1 Bed and Breakfast in the country (and #2 in the world) is the best place for some R&R. As we look forward to the months ahead, give yourself something to look forward to.  Book a room at our Galena Bed and Breakfast today. Continue reading

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

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