Today, January 17, 2023, is National Bootlegger’s Day! And as it so happens, the “CALVERT ‘KING OF THE BOOTLEGGERS’ ” was arrested in 1932 near his home in Chesapeake Beach, MD during prohibition.

Headline: The Daily Times, Salisbury, MD 12/22/1932

The “Bootlegger King” was attempting to hijack a truckload of liquor with his gang in Prince Frederick, MD using pistols, submachine guns, and shotguns… unfortunately for our bootlegger, the truck was filled with confiscated liquor being driven by Federal Prohibition Agents… (this sounds like it’s right out of a movie!).

Bootlegger’s Wreck, 1/21/22. , 1922. Photograph.

Aside from the excitement of bootleggers, hijackings, and Government agents… an interesting fact about Maryland was its stance regarding Prohibition.

The short of it was that while Maryland did ratify the Eighteenth Amendment in 1918, it was the only state that did not enforce it at the state level.  Maryland was known as the wettest state in the U.S. and the nickname “The Free State” was used regularly in defiance against Prohibition.

While intoxicating beverages were federally illegal, it appears that a blind eye was turned locally. Just as hobos had signs to let them know the lay of the land, prohibition rebels had signs to let them know of alcohol-friendly establishments. According to an article in the Baltimore Sun (published on 12/03/2003), it was stated that a red crab in an establishment’s window signified that booze was served!

Local businesses in Chesapeake Beach, MD appear to have readily served beer, however, whiskey was hit or miss, and pricier.  Below are some of the establishments that served alcohol during prohibition.

The Belvedere Hotel
The Casino
Water Edge Hotel/Marinelli’s Hotel


The 18th Amendment (aka Prohibition) was ratified by Congress in 1919 but just over a decade later, it was overturned by the 21st Amendment in 1933.  The ‘Roaring 20s’ might not have been so roaring without prohibition!

Click here to read more about Maryland’s interesting and very lenient stance on Prohibition in the Fall 2019 newsletter:…/2019-Fall.pdf

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