A small little town called Shakopee, on the outskirts of Minneapolis, used to buzz with electric energy on Saturday nights in the 1930s. Laughter, music, and the occasional quarrel broke through windows of taverns.

The parking lot outside the Mill Pond Club — which offered every form of gambling found in Las Vegas at the time — was stock-full. Men swiftly folded winnings into their wallets at the Pullman Club, which held a slot machine room everybody knew about, even the police.

Shakopee was a Midwest hub for drinking and gambling when those activities were illegal during Prohibition, according to David Schleper, a Shakopee Heritage Society historian.

Back then, Shakopee was nicknamed Little Chicago.

Former journalist Rufus Jarman once wrote in the Saturday Evening Post that Little Chicago was “where residents of Minneapolis and St. Paul used to go for their Sunday cocktails, which they couldn’t buy at home, and to dine at one of several restaurants that featured thick steaks and slot machines.”

So it was only fitting that Canterbury Park’s new fine dining restaurant would be modeled after a speakeasy, with black table cloths, old-fashioned decor, dark wooden tables and thick steaks.

And that its name would be Little Chicago.

The restaurant, set to open May 16, will add one more option to Shakopee’s narrow list of fine dining restaurants, Canterbury spokesman Jeff Maday said.

“It’s more like an East Coast chophouse,” he said.

They looked at the Shakopee market and concluded a fine dining venue could work at Canterbury.

“It is a new frontier for us but with the staff we have now and the fine dining experience they have, we can meet a demand that exists in this market but is not being served,” Maday said.

Maday said millions of dollars went into renovations this year, which also included the expansion of a card casino and several new counter dining options.

The addition of Little Chicago is exciting, Maday said, because it will be the only restaurant at Canterbury that will function year round. The hope is that the restaurant will keep people coming to the tracks whether it’s snowing or sweltering outside.

Canterbury will also take over some of the food stands that used to be run by outside vendors. Famous Dave’s on the second level, for example, will be called Pit Boss, with Texas-style barbecue. A coffee shop called Morning Line Brew will serve Starbucks products. And Pablo’s, a Shakopee Mexican restaurant that sold food during live racing, won’t be returning this year. Instead, Canterbury will open its own Mexican food stand and call it Canterbury Cantina.

All of these changes will take effect by the time live racing begins on May 3.

South regional editor

Deena is the regional editor for Shakopee, Jordan, Prior Lake and Savage and is passionate about uncovering the truth. Deena also enjoys gardening, playing tennis and up-cycling furniture.


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