The Top 10 Restaurants In Waukesha, Wisconsin

Photo of Haley Henschel
9 February 2017

Once renowned for its clean spring waters, Waukesha, Wisconsin is now taking center stage for its eclectic art galleries, popular concerts, scenic hiking trails and, most notably, its evolving lineup of local dining establishments. We explore the top restaurants in ‘Spring City,’ from unexpected foodie havens dotting the Fox River to hole-in-the-wall cafes that will make you feel like a regular by your second visit.

Independence Day parade in downtown Waukesha, WI | © Scott Feldstein/Flickr

Café de Arts

Cafe, American
Map View
An aerial view of Cafe de Arts and the surrounding area
An aerial view of Cafe de Arts and the surrounding area | Courtesy Cafe de Arts
You won’t have trouble finding Café de Arts – it is housed in a magenta building with large, vivid sunflowers painted on it. Abstract pieces from local artists also cover the walls on the inside of the quaint European-style cafe, keeping it fresh and bright even on the rainiest day. The friendly Turkish couple that owns the Café de Arts bakes fresh goods every morning which you can enjoy with a cup of coffee, or as a side with a Panini or bowl of soup. Intimate and trendy, Café de Arts is the perfect place to snag a warm breakfast or meet up with friends on your lunch break. In a rush? Since the business doubles as a micro-roastery, patrons can purchase its custom-roasted coffee to brew at home, too.

La Estación

Restaurant, Mexican, $$$
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La Estación is worth visiting for the setting alone—how often do you get to dine in an old-fashioned train car attached to a 134-year-old Victorian Gothic railroad station? This Mexican restaurant is known for its stunning, authentic venue – the station’s clock still stands guard in the foyer, and a Milwaukee artist’s paintings of Frida Kahlo and Diego Rivera grace the wall. Try one of the original seafood dishes, like the tangy shrimp with orange and tequila, or a Mexican classic, like the charcoal-grilled beef steak served with a gooey cheese enchilada and guacamole, followed by a generous scoop of fried ice cream (the most delicious oxymoron to ever exist).

Generations at 5 Points

Date night just got a whole lot swankier. Relatively new to the Waukesha dining scene, Generations at 5 Points has already made a name for itself as the area’s go-to tapas spot. The menu rotates every month to highlight the season’s finest ingredients; a typical winter dish might be macadamia scallops, baked and served on cilantro basmati rice with a guava chili glaze, or lobster mac and cheese made with a sharp white cheddar sauce, penne pasta and truffle oil. A glass of sangria is the perfect accompaniment to a meal enjoyed in the cool, almost ethereal blue glow of Generations at 5 Points.

Generations at 5 Points, 294 West Main Street, Waukesha, WI, USA, +1 262 446 3300

Key Westconsin

The warm waters and lush breezes of Florida are about 1,000 miles away from Wisconsin – and can feel even farther in the dead of winter – but don’t let distance get in the way of enjoying Southern fare. Key Westconsin, located on the Fox River in historic downtown Waukesha, prides itself on being a ‘gluten-free paradise’ serving up healthy, tropical meals that mesh the Dairy State with the Sunshine State in a fun, vibrant venue. The menu is seafood-heavy, featuring entrées like whitefish sautéed with lemon pepper, and crab cakes served with a house-made Key Lime aïoli sauce. Alternatively, try the chicken breasts with caramelized onions and pineapple juice, a dish meant for ‘landlubbers who enjoy the original boneless fish fillet.’

Key Westconsin, 331 Riverfront Plaza, Waukesha, WI, USA, +1 262 446 2346

Mainstream Bar & Grill

Bar, Restaurant, Contemporary, American, $$$
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Oscar's Frozen Custard
Oscar's Frozen Custard | ©
A good burger isn’t a rarity in Waukesha, but for a truly astounding, life-changing burger – said with only a little exaggeration – Mainstream Bar & Grill is the spot. Inside, the curvy wooden bar hugs the contemporary, casual dining area that is accented with exposed brick walls and filled with sports memorabilia and flat-screen televisions. Its the perfect spot to cheer on the Green Bay Packers, Milwaukee Brewers or Milwaukee Bucks while noshing on sports-bar classics like Tater Tots (make them Super Tators, a Mainstream favorite, by adding Ranch dressing, bacon and cheese), chicken wings, grilled flatbreads or – you’re in Wisconsin, after all – battered cheese curds. There is plenty of live entertainment too, with karaoke every Wednesday and an assortment of local musicians throughout the week.

Oscar's Frozen Custard

Restaurant, Fast Food, Cajun
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The sculpture behind the bar on the first floor of Taylor's People's Park
The sculpture behind the bar on the first floor of Taylor's People's Park | © James Carlson/Flickr
Whether it is high school students out for a first date, a family stopping by for a mid-day treat or a youth soccer team meeting up for a post-game meal, no spot brings Waukeshans together as well as Oscar’s Frozen Custard. Blame its affordable, old-school crowdpleasers, such as the Cajun chicken sandwich, onion rings and peanut butter cup sundae, or the Oscar Burger, chili cheese fries and a cone of frozen custard. A visit to Oscar’s will likely result in a decision to abandon your weight-loss resolution, but trust us – it’s worth it.

Taylor's People's Park

Gastropub, American, $$$
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A devastating fire in 2011 seemed like the end of Taylor’s People’s Park as Waukesha knew it, but after months of renovations it was back – and has since become one of the city’s most beloved drinking and dining spots. A funky sculpture made of a collage of dolls and figurines, which was restored after the fire, hangs above the ground-floor bar to greet entering patrons. Not a single wall or corner in the Civil War-era building is exempt from displaying a piece of local art. Once seated, take your pick of one of the delectable sandwiches, such as the seared tenderloin with tarragon, bleu cheese burger or pesto-chicken sandwich, or order multiple appetizers from a tapas-style meal to share with friends.

Rochester Deli

Deli, American, $$$
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Family-owned and treasured by locals, Rochester Deli is known for having the best Reuben sandwich in town – grilled like a Panini, it features a dab of horseradish cream for extra kick. Reubens aren’t the only thing they do well, though – just a single slice of cake, pie or torte from the display case will win you over. Traditional deli fare like soups, sandwiches and salads are also on the menu, while hors d’oeuvres, and even wedding cakes, are available. It is no wonder M Magazine readers and editors voted it Best Deli in the Milwaukee area in 2012.

The Steaming Cup

The Steaming Cup is all about the details; from the guitars, coffee paraphernalia and artwork on the walls to the extensive menu featuring over 120 different kinds of tea. Most importantly, though, it is about making you feel like you are a part of the neighborhood, no matter where you are from, which is why it is one of the most popular hangout spots in the downtown Waukesha area.

The Steaming Cup, 340 West Main Street, Waukesha, WI, USA, +1 262-522-3605

Weissgerber’s Gasthaus

Scour the entire metropolitan Milwaukee area and we bet you won’t find German cuisine and atmosphere to beat that at Weissgerber’s Gasthaus. Its decor and architecture – which include a cozy rock fireplace on one wall, stained glass and intricate murals of landscapes on another – evoke the vibes of a country inn in the hills of Germany. The extravagant Friday fish fry, which comes with sides of potato salad, coleslaw, rye bread, French fries, potato pancakes, apple sauce and tartar sauce, is highly recommended, or take your pick from a multitude of traditional entrées like wiener schnitzel, sauerbraten or veal Emmental. On Wednesday nights during the summer, make time in your visit to check out the ‘Wednesday Night Classics’ vintage car show that attracts visitors and their vehicles from miles around.

Weissgerber’s Gasthaus, 2720 North Grandview Boulevard, Waukesha, WI, USA, +1 262 544 4460

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