Steakhouses in Cudahy

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Jackson Grill: A User's Guide

Acclaimed Supper Club | Steaks and Seafood | Massive Portions | Brandy Old-Fashioned Cocktails | Retro Vibe
Sample Menu
  • Appetizer: hand-cut duck-fat fries served with housemade aioli
  • Entree: 24-ounce Black Angus bone-in rib eye with gorgonzola butter
  • Side: garlic mashed potatoes
  • Cocktail: brandy old-fashioned sour
The Vibe: If one phrase best sums up Jackson Grill, it's "old fashioned." This descriptor applies equally to the decor of candlelit white linens and to the way the same family has run the establishment for decades. It's also the name of one of Wisconsin's most beloved cocktails, which the restaurant's bartenders strive to perfect.

Inside Tips
  • All of Jackson Grill's dinners come with housemade soup. If you get the opportunity, select the crab bisque, which has received praise from both Third Coast Daily and the Milwaukee Journal Sentinel.
  • Arrive hungry. In addition to soup, each dinner also comes with salad, a breadbasket, and a complimentary bowl of olives. The entrees are also so big that you "might have to call in reinforcements for desserts," according to the Milwaukee Journal Sentinel.
While You're Waiting
  • Check out the collection of framed signatures from local celebrities and venerated Wisconsin athletes in the foyer. A few of these famous folks are regulars, so try not to kiss the autographs in case they see you.
  • Try to spot Chef Jackson. He's been known to make the rounds in the dining room, chatting with guests and asking how their nights are going.

3736 W Mitchell St
Milwaukee,
WI
US

5 O'Clock Steakhouse: A User’s Guide

Award-Winning Steak House | Classic Surf 'n' Turf | Live Entertainment | Californian Wines | Supper-Club Decor

Sample Menu

  • Appetizer: shrimp cocktail
  • Entree: bacon-wrapped fillet with blue cheese
  • Drink: Rodney Strong merlot from Sonoma

When to Go: Try to plan your dinner for a Friday night around 8 p.m. That’s when musicians hit the adjoining Alley Cat Lounge stage, playing everything from oldies and jazz to modern rock and R&B.



Inside Tip: Show up hungry. All meals come with a salad, relish tray, and sourdough bread with butter and honey. A side of butter-sauteéd mushrooms also accompanies every steak.



Media Mentions: Over the years, 5 O’Clock has drawn national attention. The Travel Channel featured it on the program Steak Paradise, Saveur magazine named it one of the best steak houses in the country, and Travel + Leisure said it has a "Mad Men vibe."



Behind the Name: According to the restaurant's lore, the steak house got its name from an alarm clock that would ring every day at 5 p.m., alerting customers that it was time for a free drink.



While You’re in the Neighborhood
Before: Tour the Tripoli Shrine Center (3000 W. Wisconsin Avenue), a replica of the Taj Mahal and a member of the National Register of Historic Places.

After: If the entertainment at the Alley Cat Lounge isn't to your taste, head over to The Coffee House (631 N. 19th Street), which offers acoustic music and poetry performances.

2416 W State St
Milwaukee,
WI
US