319 Meeker St. Galena, IL 61036




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

Welcome to Jail Hill Inn in historic Galena, Illinois

Thank you for your interest with Galena’s newest lodging establishment.  I couldn’t be more excited to share my love for history, elegance and hospitality than with the creation of the new Jail Hill Inn which I purchased in January 2015. The building itself has unmatched history in the city of Galena, having been the county jail from 1879-1975. It’s solid and ornate construction will thrill the history and architectural seekers and it’s views of Galena and location to the downtown district are incredible. Currently the business just passed zoning in the city to become a 6 room small inn and I am going finalizing my architectural plans and getting bids from contractors for the build out.

There will be six guest suites on floors 2, 3 and 4 with the first floor featuring the lobby, dining room, lounge, kitchen and innkeeper’s quarters.  Rooms are currently being designed with all the latest amenities while celebrating old world elegance and the local history.  I look forward to sharing the progress of the transformation of this project and encourage you to check back often and share with your friends. I hope to have Rooms open by October 1, 2015 or sooner and this page will have the latest news at all times with anything regarding the  Jail Hill Inn.

Thank you and I am so invigorated to turn a large dream of mine, into a reality and am so thankful to so many people out there that have made this moment possible for me!

Below are some beginning photos of the building exterior and interior and very special thank you to my friend, Fallon Oldenburg at www.fallondoyle.com for the the photo shoot and look for more fun photos from her!

Matthew Carroll


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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.