Toledo, Ohio audio tour: Unholy Toledo Tour: Gambling and Gangsters in the Glass City

Unholy Toledo Tour: Gambling and Gangsters in the Glass City

Driving Tour

120 mins

About the Tour

This is an updated tour with new locations and stories added!

In 1931, during the era of G-Men, speakeasies, and Pretty Boy Floyd, a gang of Detroit wiseguys led by Thomas “Yonnie” Licavoli arrived in Toledo and brought with them a wave of violence unseen in Toledo's past: 14 murders in 36 months. Are you ready for the inside story? Welcome to the Unholy Toledo Tour!

Get ready for a unique drive – and a trip back in time. Along the way, you’ll:

• WITNESS Toledo as it was during the unholy years, when the Tenderloin district was as infamous as the Glass City’s gambling halls.
• STAKE OUT the hot spots and hit spots.
• INVESTIGATE the Licavoli Gang, club owner Jack Kennedy, kingpin Jimmy Hayes, and a cast of characters — major and minor, good and bad, but all historically accurate!
• EXPLORE Toledo from World War I through to the Prohibition Era and the end of World War II.

The most sensational crime of the era happened in July 1933 when a young club owner and bootlegger named Jack Kennedy was gunned down in Point Place. This tour tells Jack's story, from start to finish, over the course of a two-hour-long driving tour covering the downtown area and northern Toledo.

Make sure you check out our store after your tour and pick up some Unholy Toledo Tour swag! And don't forget our other tours at

The material for this tour is made possible by the outstanding research of two local historians, Ken Dickson and Terry Shaffer. Ken Dickson is the author of Nothing Personal Just Business, Prohibition and Murder on Toledo's Mean Streets, and Something for Nothing: Gambling in the Glass City. And Terry Shaffer is the author of Illegal Gambling Clubs of Toledo. Credit is also due to our local newspapers for their in-depth reporting during this turbulent time in Toledo history.

Music for this tour is provided by

Tour Producer


Tedd Long

Welcome to Northwest Ohio! I'm Tedd Long, writer and curator of I love introducing guests to my favorite local history stories and showing off the Maumee Valley. I also enjoy hearing people who have lived here all their life say things like, "Gee, I didn't know that!" or "I never knew that was here!" Plus, I'm known for never missing a good meal so I'll make sure to pass along where to catch a delicious bite to eat or enjoy a relaxing drink while we're out and about. Whether we're walking or driving—I have so much to share! Let's go...

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Major Landmarks

  • Valentine Theatre

  • Central Post Office

  • The Warehouse District

  • Cullen Park

  • Dixie Highway

  • The Villa

  • Commodore Perry Hotel

Directions to Starting Point

Our tour begins in front of the Art Tatum Celebration Column, located at the corner of Madison and Superior in downtown Toledo. The address is 507 Madison, directly behind the Huntington Center.

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Places to stop along the way

Looking for a place to grab a bite to eat along the way? At the beginning of our tour, I'd recommend the Coney Island Hot Dog ($) or Georgio's ($$$$) near the Valentine Theatre to get started. Towards the middle of the tour, I'd check out Michael's Bar and Restaurant at Michigan and Monroe ($$) or wait until we hit Point Place and try Webber's Waterfront Restaurant ($$$).

Best time of day

Traffic is generally not an issue along the tour, but it can be a problem getting to and from the tour route during peak commuting hours. On work days, it is best to begin after 10 a.m. and conclude before 4 p.m. Traffic is light after 6 p.m. but be sure you will have enough daylight to see the sights.


Please obey the rules of the road and drive safely. Always make sure your vehicle is out of the way of traffic when pulling over for tour presentations. All of the roads used are public and traffic on some can be fairly heavy. Use caution, especially when pulling into traffic or slowing for a stop. Obey all posted speed limits and traffic regulations. Distracted driving is dangerous,

If you exceed posted speed limits, you may bypass VoiceMap directions and information.


Learns lots and have lived in Toledo my entire life.

Posted by Anonymous Explorer , 9 months ago

Outstanding - we really enjoyed this on a beautiful sunny winters day.

Posted by Anonymous Explorer , over 1 year ago

Great tour - did not do well with direction !!!

Posted by Anonymous Explorer , over 1 year ago
Preview mode limited to first 3 locations.
Unholy Toledo Tour: Gambling and Gangsters in the Glass City