319 Meeker St. Galena, IL 61036

815-777-3000

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Things to do in Galena

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

Exciting Changes in Downtown Galena IL This Summer!

Explore Downtown GalenaThere have been some big changes to downtown Galena IL this summer in response to the COVID-19 pandemic, but we think they’ve been pretty great changes for the most part.  We recognize that travel feels a little different to all of us right now, but we hope you feel comforted knowing our entire town is working hard to create a safe and healthy environment for all who choose to visit!  You can find what we’re doing, specifically, on our website.

Travel studies released recently have shown that getaways that are closer to home and to smaller towns are considered to be one of the best options.  That is great news for Galena, as we’re located just under 3 hours outside of Chicago, and easily drivable from other major cities like Milwaukee, Minneapolis and St. Paul, and Des Moines. When you get to downtown Galena IL, you’ll notice a few things are different!

The town of Galena has decided to turn its Main Street, which is normally bustling with both cars and people, into a pedestrian-only zone.  It’s transformed our town and is allowing our local businesses to flourish once again.  That is, of course, provided you take the time to get here and join us!  With downtown Galena closed to traffic, staying nearby and within walking distance is more important than ever. Our Galena Bed and Breakfast is the perfect place to stay, as we’re located just off Galena’s Main Street, and within easy walking distance to everything downtown Galena IL has to offer.  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

Our 10 Favorite Things to do in Galena For Spring

10 Things to do in Galena IL This Spring

There are signs of spring in the air, and we couldn’t be any more excited than we already are!  If you’re planning a visit to Galena this spring, we bet you’re looking for the ultimate guide of things to do in Galena, right? We’re here to help! And, if you’re not yet planning to visit us, then maybe it’s high time you clear those calendars and get down here!

A night at the Jail Hill Inn in historic downtown Galena is more than worth the trip. You’ll be pampered from the moment you first arrive. Beyond our doors lies the charming town of Galena, filled with great restaurants, plenty of independently-owned shops, historic venues, scenic countryside, wine tasting, a brewery, and a distillery, and so much more. Come experience this incredible destination this spring, and book your room at our Galena Bed and Breakfast today! Continue reading

A New Year, a New Getaway to our Galena Bed and Breakfast

Stay at the Best Galena Bed and BreakfastA New Year is upon us, and while we’re all busy making New Year’s resolutions, we have one more you should add to your list:  getting away to our sensational Galena Bed and Breakfast!  That’s right!  In this new year full of hopes, dreams, and promises, we think you should carve out some extra time this year to take care of yourself.  Even better, come stay with us, and let us take care of you! After all, pampering our guests is what we do best.

It won’t take you long to get here, and you’ll be forever glad you did. Book your room at our luxury Galena Bed and Breakfast today! Continue reading

10 Things You Simply Must do in Galena This Winter

10 Things to do in Galena This WinterHave you ever visited Galena during the winter? It’s a wonderful place to visit, even when there’s snow on the ground!  There are plenty of delightful things to do this winter, and we have a great guide for you. Head out on a cross country skiing adventure, explore our vibrant and historic downtown, or sit back and savor the luxurious accommodations found at our Galena Bed and Breakfast.

Galena has long-been a popular getaway destination for those living in or around the Chicago area, and these winter months should be no different. Even if you don’t love spending time outside during the winter, the chance to stay at our romantic Inn is more than worth the time it takes to get here. Your day will start with a delicious breakfast, but that definitely isn’t the end of our award-winning hospitality.  In the afternoon, join us for a delicious wine and cheese hour, along with some delicious fresh cookies, hot from the oven. Come see it for yourself, and book a room at our Galena Bed and Breakfast 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!