319 Meeker St. Galena, IL 61036

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Things to do in Galena

Try These Things to do in Galena IL This Summer

Explore all of the wonderful things to do in Galena IL This SummerAre you feeling the itch to travel, and to get out and explore? Your dreams of a European vacation may be delayed again this summer, but there are plenty of things to do in Galena to make up for it!  All you have to do is get here and enjoy a stay at Jail Hill Inn, and all of the area’s top attractions and activities will be at your fingertips!  From relaxing at our stunning Galena Bed and Breakfast to getting outside and exploring the many trails and attractions in the area, you won’t run out of things to do in Galena IL this summer!

We love sharing our little piece of the world with our guests from around the world and pride ourselves on curating a memorable experience for all who visit us.  Our hospitality starts the moment you step through our doors, with chilled champagne and custom chocolates waiting for you in your suite.  From there, we encourage you to explore downtown Galena, visit the charming shops and local businesses that call this area home, and experience all of the small-town charms this area is known for.

Ready to travel?  Book your room at our Galena Bed and Breakfast today! Continue reading

2021 Roundup – Our Favorite Things to do in Galena This Year!

This beautiful waterfall is one of our favorite things to do in Galena this summer

Nothing beats summer vacations spent playing, seeing new things, and lounging under the warmth of the afternoon sun.  As we gear up for what is looking to be a busy and exciting summer, we’d like to share with you some of our favorite things to do in Galena.  Small towns like ours are still poised to be popular getaway destinations this summer, as travelers stick to domestic destinations and small towns in particular.

You’ll not only find plenty of things to do in Galena, but you’ll find fewer crowds and unparalleled luxury at our Galena Bed and Breakfast. Galena’s business owners have consistently worked hard over the past year to bring you plenty of fun, all while keeping public health and safety in mind.  Jail Hill Inn recently received the Traveler’s Choice Award from TripAdvisor, and we were once again named in the top 10 Bed and Breakfasts around the country, making it three years straight to earn this honor!

We’d love nothing more than to see you this summer or fall, and to give you the most relaxing and enjoyable getaway possible.  We’re booking up quickly, though, so make sure you book your room at our Galena Bed and Breakfast today! Continue reading

Enjoy These Great Finds in Downtown Galena!

Explore Downtown GalenaDowntown Galena is a wonderful place to spend a bit of time this summer!  The charming, historic Main Street is lined with incredible shops, restaurants, historic attractions, and more.  Our shop and restaurant owners have been working hard over the last year, too, to make the experience a safe and enjoyable one in the face of the COVID-19 pandemic.  That includes part of downtown Galena being closed down to cars to make room for outside dining, too!

Jail Hill Inn is just steps away from Main Street in downtown Galena, which means when you stay here, you’re at the heart of the action. You can shop ’til you drop, enjoy a delicious dinner for two, access the popular Galena River Trail, or even sample a bit of local wine and beer without hopping in your car!  It’s one of the many great things about staying at our Galena Bed and Breakfast.

Not only that, but you’ll find our sumptuous accommodations far exceed your expectations, with a gourmet breakfast and delicious wine and appetizer tray served fresh to you each and every day. This summer, come explore the fun and multi-faceted town of Galena with us!  We’re only a short drive away from major midwest cities like Chicago, and offer you an escape to an entirely different world.  What are you waiting for?  Book your room at our sensational Galena Bed and Breakfast today! Continue reading

Is the Trip From Chicago to Galena Worth It?

Enjoy the Trip from Chicago to GalenaChicago is the nearest big city to Galena, and it only takes about 3 hours to get from Chicago to Galena.  Even so, you might be asking yourself if it’s worth making the trek from Chicago to Galena.  The answer to that is a resounding yes.  Of course, we think the opportunity to visit our Galena Bed and Breakfast is more than worth the effort, but visiting us is about so much more than the luxury accommodations you’ll find once you’re here; it’s also about this incredible, historic town that you’ll get to enjoy once here.

Galena is steeped in history, and it’s hard to get a sense of appreciation for it from afar. Dating back to its earliest days as a mining town, and later as the home of famed U.S President Ulysses S. Grant, there is much to see, do, and experience once here.  And, just as with any great road trip, the journey to get from Chicago to Galena is a beautiful one and is filled with plenty of small towns and picturesque vistas to enjoy along the way. What are you waiting for? Hop in the car, and head on out to Galena. Just make sure you have reservations at the incredible Jail Hill Inn before you go! Continue reading

How to Enjoy a Winter Getaway at our Galena Bed and Breakfast

The #1 BEST Galena Bed and Breakfast for your winter getawayIt’s not yet officially winter, but it’s getting chilly here in Galena and we’re preparing for the cozy and romantic season ahead.  Winter isn’t considered to be peak travel for many destinations around the country, Galena included.  But, there are plenty of reasons to plan a winter getaway – and when you do, there’s nowhere better to spend it than at our Galena Bed and Breakfast.

When it comes to things to do in Galena this winter, there’s more than enough to keep you busy, too.  Enjoy some socially distanced shopping or dining in downtown Galena, get out on the trails for a little winter hiking (or cross country skiing or snowshoeing), head to Chesnut Mountain for some skiing, or otherwise take the time to breathe the fresh air of Galena Country and sit back, relax, and let us take care of you!  Book your room at Jail Hill Inn, and get ready for the winter getaway of a lifetime.

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Our Bed and Breakfast in Illinois is the Perfect Romantic Getaway

Romantic getaway at our Bed and Breakfast in IllinoisIf there’s one thing we do well at our Bed and Breakfast in Illinois, it’s cater to the romantics among us. In fact, romance is at the very heart of everything we do here. Whether it’s in the luxury touches of our spacious guest rooms, our delicious breakfast each morning of your stay, the luxury touches and amenities you’ll enjoy throughout your time with us, or just the private oasis that is our Bed and Breakfast in Illinois, you can be assured that this is one romantic getaway you won’t forget.

And that’s to say nothing about the romantically charming town of Galena itself!  This historic little town, just a few hours west of Chicago, seems as though it was built with romantic getaways in mind.  There are plenty of romantic things to do in Galena, including wine and other tastings, shopping, romantic dinners, picturesque strolls by the river, and so much more.

Come check out this sweet little town this winter, and give yourself the chance to get cozy at our romantic Bed and Breakfast in Illinois.  Book your getaway today! Continue reading

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! Continue reading

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

We’re Still the Best Galena Bed and Breakfast

Stay at the Best Galena Bed and Breakfast This FallSince first opening our Galena Bed and Breakfast in 2015, Jail Hill Inn has enjoyed a number of awards and accolades, including our crowning achievement of being named the #1 Bed and Breakfast in the country, and the #2 Bed and Breakfast in the world, in 2019.  Those awards from TripAdvisor led us to our best year on record, and we entered 2020 with a great sense of hope and purpose.

While 2020 has certainly been a challenge, with the COVID-19 pandemic affecting not just our business, but those around the country, we’re still so thrilled to be open and busy welcoming guests this summer. This summer has brought many changes to Jail Hill Inn. We no longer host an afternoon wine and cheese hour, but instead deliver individual trays to your suites each afternoon, our breakfasts are now served at socially distanced tables (or to the privacy of your suite), and masks are required on our property.  Moreover, downtown Galena has, at least temporarily, closed down Main Street to vehicle traffic and has moved to dine outdoors onto the new Pedestrian Zone.

It’s been challenging but fun to rise to the occasion and pivot our business model to meet the demands of this pandemic, but it’s also been heart-warming to see how the entire town of Galena has come together and rallied to keep our thriving tourism destination a safe and welcoming space to getaway.  In midst of all of this, we’re also incredibly delighted to once again be named at the top of the list of the Best Bed and Breakfasts in the country.

For 2020, our Galena Bed and Breakfast ranks as the #3 B&B in the country, and #11 in the world.  It may not be #1 and #2, but we’re still near the top of the list, and that is something we’re incredibly grateful for! If you’re looking for a beautiful, safe, and welcoming getaway anytime in the near or distant future, we hope you’ll consider staying at Jail Hill Inn, so you can see what it’s like to stay at one of the best Inns in the world. Book your room at the Best Bed and Breakfast in Galena today! Continue reading

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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!