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The Five-Point Weekend Escape Plan

Explore the Newer Side of Milwaukee

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5. Oddball Day


Leon’s Frozen Custard, a local institution, has been open since 1942.  

Fuel up for a day of retro fun with a honey latte (from $3.25) and potato-bacon breakfast burrito ($5.45) at Alterra at the Lake. Drive less than ten minutes away to Riverview Antique Market and take your time perusing the booths of 50 dealers selling mostly 18th- through 20th-century folk art and furnishings, including a twenties chrome desk-lamp with attached ashtray ($75, booth #8). Then stop by Old World Third Street to see sausage emporium Usinger’s, which has been open since 1880, before having lunch at Leon’s Frozen Custard, a 1942 drive-in diner serving chili dogs ($1.96), homemade sodas (from $2.76), and custard ($1.20). Minutes away is Holler House (2042 W. Lincoln Avenue, 414-647-9284; $4 per game, plus pin-setter tips), the oldest sanctioned bowling alley in the country. With a little notice, 85-year-old owner Marcy Skowronski will hire a pin boy to work the two basement lanes, or you could just get a Miller shorty ($1.50) at the upstairs bar to hear her tell stories about the bras hanging from the ceiling. Afterward, head to Angelo’s Piano Lounge (1686 North Van Buren Street, 414-347-4144), where a jukebox playing Peggy Lee and Duke Ellington entertains when local performers aren’t reviving Rat Pack–era tunes on a dimly lit stage. Stay in the sixties by meeting your reservation at the supper club–style Five O’Clock Steakhouse. Orders are taken at the bar before you’re seated in a dining room decorated with year-round Christmas lights and mirrored walls. Get the perfectly buttery filet, done as a “kings cut” ($40) or daintier “ladies cut” ($28), and watch it appear shortly after you reach a table already dressed with salad, bread, and a relish tray.


Published on Aug 11, 2011 as a web exclusive.

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