319 Meeker St. Galena, IL 61036




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.

Continue reading

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.

Continue reading

Discover Wineries in Galena

Wineries GalenaGalena, a town put on the map because it was the home of President Ulysses S. Grant, is a wonderful getaway destination throughout the year. It’s picturesque and quiet streets are filled with quaint shops and boutiques, gourmet restaurants, spas, and wineries. Even better, all of this and more is easily attainable, as Galena is only a one-tank trip from many large Midwest cities.  Throughout the year, there are a variety of events that draw wine lovers to Galena, and numerous wine bars and wineries to keep the fun flowing throughout the remainder of the year.  Book your room at our newly renovated and historic Galena Bed and Breakfast, and sip your way through Galena’s best wines. Continue reading

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

The Exciting Transition: Neglected Old Jail to a Luxury Small Inn

Demolition and reconstruction is now in its 7th month and it has been an amazing journey.  Filled with highs and lows and still about two months to go until Jail Hill Inn will welcome its first overnight guests. In the end, from purchase of the building, securing the needed permits, demolition and full reconstruction – the project will have taken a year.  As construction enters its nearly final phase, the focus is on insulation, drywall, taping walls and priming.  Then final paint will put put on the walls, along with trim, doors, hardware, lighting and flooring.  The coordination of workers can be complex with so many projects relying on something else to be done before it can be.

In a couple weeks, Jail Hill Inn will be part of the 48th Annual Tour of Homes in Galena.  The property will not be complete, but will welcome close to 1000 people through its doors to discuss the history and purpose of the building from 1879 and get a sneak peak of how it will look when its complete.

In the next few weeks, Jail Hill Inn’s website will be redesigned and the online reservation system will be up to start taking reservations.  Keep checking this site and the Facebook page as we continue to detail the progress and final stages!

The Summer of Progress

July has been a busy and exciting month at Jail Hill Inn.  With construction nearing the halfway point, much focus has been put on final framing of rooms, how electrical, plumbing and heating/cooling will lay out.  In addition, Jail Hill Inn and myself were featured on KCRG-TV 9 (Cedar Rapids, Iowa) on a special segment showcasing young entrepreneurs in Galena.  The positive feedback has been incredible with this large and complex project.  I have been spending my days picking out furniture, design concepts, flooring, towels, sheets, appliances, window treatments and many more items that will be required to be ready for opening day.  Below are some fun photos of the exterior and progress thus far.  Enjoy and I look forward to updating on an official opening day soon and launch of the online reservation system, etc.

June: Four Months Away from Opening

Summer and warm weather is in full swing in Galena and things are getting really busy at Jail Hill Inn.  Carpenters, plumbers and electricians are in the building everyday working floor by floor and old walls are being taken out and new walls are being constructed.  In the end, when construction is complete, Jail Hill Inn will have 7 new bedrooms, 9 new bathrooms, 6 sitting rooms, 8 fireplaces, 1 kitchen, 2 laundry rooms, 1 dining room capable of hosting 15 people and three new staircases in 8,000 square feet of renovated space between four floors.  Oh, and one really big stone wall outside!

Jail Hill Inn is also excited to announce that the property will be featured in this year’s Historic Tour of Homes in Galena on September 26 and 27, 2015.  The property was featured several years back under different ownership and not the entire property.  This year, all four floors will be viewable as finishing touches may still be underway as we prepare for the October opening for the business.  This will be a great opportunity to tour the property and learn some of the history of the building while seeing all the exciting changes the renovation has created.

Coming to life in May

It’s been an exciting month as intense focus has been given to the exterior property at Jail Hill Inn.  On May 5th, work began to tear down and rebuild the stone wall that is along the driveway.  With the help and expertise from Vincent’s Earthmoving in Elizabeth, Illinois, a new taller and more substantial wall was built and completed on May 12.  Over 70 tons of stone were put in place and the wall spans nearly 20 feet in some parts.  This wall not only enhances the property appearance, but also stabilizes the neighboring property and allows for proper water run off .

In addition to the stone wall, the ornate and original fence in front of Jail Hill Inn was completed on May 12.  The fence was originally white and was painted a glossy black to better blend in with the property and showcase the building.  Numerous hours were required to paint, given the detail and angles that were needed to be painted.  I have even had help from some of my neighbors on the project and everyone is excited, to see it complete

Inside, Jail Hill Inn has been undergoing major demolition work to prepare as contractors begin the construction inside very soon.  Existing walls that will no longer be needed or need to move, based on the newly designed plans, are being taken out.  Existing bathroom fixtures that show age and distress have been removed and discarded, to give way for the 7.5 new bathrooms that will be added to the building.  Water and electricity were tuned on in the building recently as the property had incurred frozen and burst pipes from its sitting vacant for 2 years.  The broken pipes were shut down or repaired and everything is in great working order.

I have also been continuing my work with the State of Illinois Historic Preservation Agency with acquiring historic tax credits with Jail Hill Inn.  These credits provide financial relief to property owners who are renovating historic buildings.  There is an extensive application process, site visit and importance given to maintain as many original and historic features as possible.  I look forward to continuing my steps with the agency and showing my exciting vision with this historic and important structure in the city of Galena.  Here is the link that detail the historic tax credits:  https://www.illinois.gov/ihpa/Preserve/Pages/Funding.aspx

Thank you to everyone who has shared in my excitement and has stopped by to see the property or liked us on Facebook, etc.  Your feedback and support are important in this process and I’m so excited to share this journey as it continues.

I hope everyone has a productive and healthy rest of the month and look forward to sharing more updates soon!  Cheers!


April at Jail Hill Inn

Spring is in the air all over and it’s very exciting to see things come to life at Jail Hill Inn.  With this being my first spring at the property, it’s a fun mystery to see different bushes and flowers coming up around the yard and many ideas of enhancing and expanding the outdoor appearance of the property.  With the warmer weather I have begun painting the ornate fence in front of the inn from white to black!  Black will be a wonderful backdrop and complement the bricks nicely and is a wonderful clean and classic look for a property such as this.

Inside Jail Hill Inn, we recently said goodbye to the large spiral staircase that was on the first and second floor.  The staircase was determined to not be necessary as it took up a large portion of the first floor lounge and dining area and also took up 1/3 of the second floor, which will be replaced with the floor being put back in and making a very stately and charming second floor guest suite for guests.

I have also been busy meeting with contractors, finalizing bids, plans, measurements and working closely with the bank and the financial team as we craft the next steps of Jail Hill Inn as it moves from the design phase to the implementation and actual construction phase for the next 4 months.

I will be setting up the Jail Hill Inn Facebook, Instagram, Twitter, Foursquare, Google spots and Yelp and TripAdvisor once the business opens, later this year.  Please watch the site for those updates and look forward to following on social media as well!

Thanks for stopping by and I look forward to sharing more exciting progress soon!

Matthew Carroll

Jail Hill Inn

Scroll to top
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.