Jake’s Restaurant in Pewaukee is almost 60 years old, but despite many scenes like the above happening on a daily basis, it’s not caught in a time warp in the dated sense of the term. Owners Jake and Karen Replogle aim for a balance with the menus (food and drink), service and even the décor. In an era where the supper club is indubitably in vogue, the couple say they have to remind themselves that traditions like “old fashioned” and “rumaki” are now marketing buzzwords. And yet, “we were doing it before it was cool,” says Karen.
It’s old-timers, still rounding the bend from Capitol Drive to Gumina Road for reasons like the Monday night tenderloin special, who remember Jake’s history. Founder Jake Replogle Sr. bought two restaurant spaces – the first Jake’s in 1960 on 60th and North in Wauwatosa, and the present-day Jake’s in 1967, located inside an old barn on a family farm in Pewaukee. (The Tosa location closed in 2001.) Framed on the barnwood wall next to my table one evening is a Jake’s menu from the ’60s, advertising steak and onion rings for $1.95. The special runs $14.95 now but still has a solid fan base. Those folks are a key part of Jake’s audience.
Before making any changes – and those have included, over time, adding tuna tartare, grilled octopus and a roasted market fish to the menu – the couple consider whether it’s “still our style,” says Karen. Ultimately, Jake’s is a family business that still feels like one. And that could begin with a Manhattan made with your choice of bourbon and Jake’s brandied cherries, or one of the new mocktails such as the juniper-infused Gin(less) & Juice.
Jake’s Restaurant
21445 W. Gumina Rd., Pewaukee,
262-781-7995
HOURS
Daily Mon-Sat
PRICES
$18-$56
SERVICE
Experienced, professional
RESERVATIONS
Recommended
At Jake’s, entrées come with two sides or a salad. While I like a kale and romaine Caesar, I like the sides a lot more – especially the crusty, cheddar cheesy twice-baked potato and crock of creamed spinach dusted in browned breadcrumbs. You might have some to take home. Partner them with a steak – I suggest the well marbled, 35-day dry-aged rib eye ($53), adding Jake’s sweet-pungenty steak sauce and some firm, buttery sautéed mushrooms ($7.90). If you’re a tenderloin person, the filet (6-ounce, $38) is best with a classic, tarragon-laced bearnaise sauce and Jake’s haystack onion strings ($9.50) – creamy and crisp complements that add richness to the lean meat.

The seasonal touches to the taut-but-tender seared sea scallops ($37) – creamy carrot puree, tart-sweet Honeycrisp apple, toasted pumpkin seeds and anisey fennel – give it an autumnal lift that feels very Wisconsin. But I think my love of nostalgia is better served by the panko- and hazelnut-crusted walleye with lemon and brown butter sauce ($30). It’s just plain great.
And for a final course, nothing resurrects an appetite like a well-appointed dessert tray. From choices like tiramisu, crème brûlée and a toffee hot fudge sundae, we think we’ve hit the jackpot with the chewy, relatively light pavlova meringue with fresh berries and apricot sorbet.
No doubt about it: Jake’s holds the secret to longevity. But it takes experience and maturity to discover it.