Inn It To Win It
The history of The Cheshire is a storied one – filled with generations of memories. We want to preserve those stories for years to come and introduce a new generation to the charm of this iconic hotel.
Thank you so much to the nearly 90 people who shared their stories as part of our “INN It to Win It” contest. It was so hard to choose just 10 winners!
Below are the winning stories:
Andrew Belmont
The Cheshire Inn has always been a very special place for me and my family. As far back as I can remember, my grandparents would take me and my cousin Ryan there…. Read More
Shawn Stromberg
My wife, Sandra, and I spent our wedding night enjoying the Captain’s Quarters in 2004. Six months later, I learned I had testicular cancer… Read More
Kathleen Durbin
I was raised with Medart’s…nothing better! In September of 1964, I made a phone call to my mother from a payphone near the ladies room of the tavern. I told her that Rob and I were going to get married… Read More
Richard Vallat
In March of 1966 I asked my girlfriend of two years to dinner. She was very excited to learn that I was taking her to the Cheshire Inn in Richmond Heights… Read More
Dianne Steger
On June 8, 2001, we had our rehearsal dinner at the Cheshire. The problem was that at the rehearsal, the man in charge of the music for the ceremony did not show up… Read More
Karen Lee
The Cheshire Inn has been a special part of our family memories. My oldest son attended Westminster University in Fulton, Missouri, and since our hometown is Little Rock, AR, when his two younger brothers and I would visit him, we liked to stay in nearby St. Louis, as there was much more to do there… Read More
Mandy Drozda
I was 24 years old and I was, as my friends and I always did, finishing my night out at the Cheshire. I used to always say, “If you are going to Cheshire to meet someone like your future husband, then you should go home. The Cheshire is for one more drink and lots of fun.” That is exactly what I always had there. Well, it may have actually been a few more drinks… Read More
Maureen Gehrlein
We shared a very memorable New Year’s Eve at the Cheshire. At that time, I was dating the man who would become my husband, but unfortunately it was long distance… Read More
Kimberly Curran Cole
The Cheshire holds many memories for my family and me and we are looking so forward to making more memories when you reopen! It all began when my husband and I attended Washington University School of Law before we were married… Read More
Mr. and Mrs. Richard E. Adams
There are more memories than we could possibly express in a mere 300 words, so we may have to do this more than once! We watched the building being built. We’ve stayed at the inn again and again, for events like birthdays and anniversaries or just for romantic getaways… Read More


