Unholy Toledo Tour: Gambling and Gangsters in the Glass City

(80 reviews)

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

This is a 20mi driving tour

It takes an average of 120 mins to complete.

Toledo, Ohio

The United States

$14.99

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About the Tour

Step into the shadowy world of 1930s Toledo, a time of G-Men, speakeasies, and notorious gangsters like Pretty Boy Floyd, Baby Face Nelson, and Machine Gun Kelly. Brace yourself for the gripping tale of Thomas Yonnie Licavoli and his Detroit mob, who descended upon Toledo in 1931, leaving a trail of violence, unlike anything the city had seen before—14 murders in just 36 months. Are you ready for the inside scoop? Welcome to the Unholy Toledo Tour!

Prepare for a journey back in time as you:

WITNESS Toledo during its darkest days, when the infamous Tenderloin district rivaled the city's gambling halls in notoriety.
STAKE OUT the illicit hotspots and notorious hangouts.
INVESTIGATE the notorious Licavoli Gang, the enigmatic club owner Jack Kennedy, kingpin Jimmy Hayes, and a colorful cast of characters—each meticulously researched and historically accurate.
EXPLORE Toledo's tumultuous journey from World War I through Prohibition and into the aftermath of World War II.

The tour's climax centers around the most sensational crime of the era: the July 1933 assassination of Jack Kennedy, a young club owner and bootlegger, in Point Place. Experience Jack's gripping story firsthand during this two-hour driving tour, spanning downtown Toledo and the city's northern reaches.

After the tour, visit our online store and snag some exclusive Unholy Toledo Tour swag! And don't miss out on our other captivating tours at holytoledohistory.com.

Tour Producer

Tedd Long

15 tours

Hi, I’m Tedd Long—history geek, storyteller, and creator of HolyToledoHistory.com. My passion is uncovering the fascinating, funny, and sometimes jaw-dropping stories that shaped Toledo and the Maumee Valley.

Whether you’ve lived here your whole life or you’re visiting for the first time, you’ll hear things that make you say, “I never knew that!” From forgotten gangster hideouts to remarkable riverfront landmarks, I’ll take you beyond the obvious and reveal the city’s hidden history.

My tours blend rich storytelling, local legends, and insider tips—like the best spots for a cold drink, a great meal, or the perfect photo. Every route is designed so you can explore at your own pace, with VoiceMap-guided stops that bring the past to life right where it happened.

Come walk or drive with me through history. You’ll leave with a deeper appreciation for this place—and maybe a few stories of your own to share. Let’s go explore!

Preview Location

Location 39

Kennedy Hit | 5902 Edgewater Drive

Pull into the parking lot here on your right.

Roughly seven months after the murder of Louise Bell at Superior and Jackson and just a month after the fight at Acme Sales on Monroe and Michigan, the Licavolli gang came after Jack Kennedy with a vengeance. Many of Jack's frie... Read More

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Major Landmarks

Valentine Theatre
Valentine Theatre
Central Post Office
The Warehouse District
Cullen Park
Dixie Highway
The Villa
Commodore Perry Hotel
Toledo Warehouse District Association
Cullen Park
Angelo's Northwood Villa
Toledo Club
Commodore Perry Apartments

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Getting There

Route Overview

VoiceMap tours follow a route from a set starting point. It’s how we give turn-by-turn directions and tell a story greater than the sum of its parts.

Start location
623 Adams St, Toledo, OH 43604, USA
Total distance

32km
Final location
4417-4415 US-24, Toledo, OH 43612, USA
Distance back to start location

5km

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.

Show Directions

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Tips

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.

Precautions

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.

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“Great app. walk around at your own pace, stop where you want, move on or speed up when you want. Read the script before you go or during the commentary, speed it up or replay it. Repeat the tour whenever you like.”