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You are sentenced to luxury at the Jail Hill Inn, Galena, Illinois

Written By | Jun 13, 2021
Jail Hill Inn, B&B, Galena, Illinois

Jail Hill Inn, courtesy of the Jail HIll Inn

ILLINOIS:  In 2019 the Jail Hill Inn, of Galena, Illinois, was rated by the Tripadvisor website #1 Bed and Breakfast in the United States and #2 in the world, remaining in the top ten since.  The Jail Hill Inn is the result of  Matthew Carroll, a native of Galena, and his vision of re-purposing the historic building.

The Jail Hill Inn is a family affair for the Carroll family.  Matthew, together with his very supportive retired parents Terry and Ginny, turning the broken-down old brick-and-mortar county jail into a highly desirable B&B destination.

Carroll bought the 1878 former Jo Daviess County jail in 2015

The jail had been sitting abandoned for a number of years when Carroll bought it in 2015. The building was used as the county jail up until 1975 when the sheriff had it condemned.   One previous brief owner gutted all of its ironwork (prison bars and the like) for scrap price in the 1980s.

The building was then left in a state of disrepair.  The four-story Empire-style brick and Illinois limestone building measures 8,000 total square feet and cost $16,000 to build back in the day.




Jail Hill Inn, B&B, Guest Room, Galena, Illinois

Guest room at the Jail Hill Inn. Image courtesy of the Jail Hill Inn

The jail became nationally known when it elected the only female county sheriff in the nation in 1954.  “Two-Gun Emma Grebner” was widely adored for her hospitality.  The food in the county jail was often said to be better than what the inmates would have had in the outside world on their own.

Originally, the bottom two floors were designed for office on the first floor

Residences for the county sheriff and family were on the second floor. The third floor was designed to hold up to a dozen male prisoners.  The fourth top floor was designed for the occasional female prisoner.  The building featured a poured concrete over steel floor to ensure inmates couldn’t dig down and reach the sheriff’s family.

The top two floors had bars on the outside of the windows.

A YouTube video was my introduction to the Jail Hill Inn and I was stunned it was so close to home. Proving that some travel experiences are in your own backyard.

It became an anniversary destination for the wife and I. Galena is a popular destination alone for the locals but it also draws people in from all over the world as one of America’s oldest untouched cities.

There was a time when Galena was larger than Chicago. 

The area was settled in the 1690’s by the French and officially became a city in 1826 when stagecoach trails began the infrastructure of America.

People visit the Midwestern town of Galena for the architecture and history.  Much of that architecture is coming up on 200 years old now.  They also visit for shopping, dining, and recreation. The city is historically known for the mining of Galena lead as well as the home of General Ulysses S. Grant who went on to become our 18th President.

Lincoln is known to have visited Galena on more than one occasion since Grant was his top General during the Civil War.

The Galena River was once a major maritime trade route to the Mississippi

It was also the busiest waterway between Minneapolis-St. Paul and St. Louis.  Things started to go wrong for Galena when the river silted in and train transportation took over the country.  Interestingly, the railroads largely followed along established stagecoach trails of some 25 years previous establishing America’s early infrastructure.



We went to stay at the Jail Hill Inn this spring quickly learning why the B&B is so highly ranked. 

First, was the gourmet food beginning with a welcome tray featuring locally made wine. A gourmet breakfast the following morning continued the epicurean delights.

Jail Hill Inn, B&B, Galena, Illinois, travel

Breakfast at the Jail Hill Inn -Image courtesy of the Jail Hill Inn.

Second, was the precious time Matt Coller shared with us as he shared local jail house folklore.  His hometown pride was self-evident.  I think the funniest thing he told us was about the times children would sneak in the back of the jail to play cards with the inmates through their cell bars.

Other fascinating stories were related to the escapes and captures from the jail.  A final impressive aspect to our visit was the attention to details Matt put into the 6 suites of the building.

One would never think of a jail house as ever being homey but Jail Hill Inn really makes you feel at home!

While Northern Illinois may not be on your travel list, it should be.  However, fair warning, the Jail Hill Inn gets booked up for the year early!

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Read more from Mark Schwendau

About the author:

Mark Schwendau is a Christian conservative patriot and retired technology professor (CAD-CAM and web development) who prides himself on his critical thinking ability.  Schwendau has had a long sideline of newspaper editorial writing where he used the byline, “- bringing little known facts to people who simply want to know the truth.”

Mark is on alternative free speech social media platforms after lifetime bans from Facebook and Twitter and shadow bans from Instagram and Fox News commenting.  His website is I Draw I Write.

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Mark Schwendau

Mark Schwendau is a Christian conservative patriot and retired technology professor (CAD-CAM and web development) who prides himself on his critical thinking ability. Schwendau has had a long sideline of newspaper editorial writing where he used the byline, “- bringing little known facts to people who simply want to know the truth.” Mark is on alternative free speech social media platforms after lifetime bans from Facebook and Twitter and shadow bans from Instagram and Fox News commenting. His website is www.IDrawIWrite.Tech