Where to eat on Milwaukee’s east side near Oakland Avenue

Milwaukee is a city of neighborhoods, and dining critic Rachel Bernhard intends on exploring them the best way she knows how: through food. In her series Movable Feasts, she sets out to craft the ultimate meal by visiting multiple dining destinations — plus popular stops along the way — to get a better taste of what each of the city's distinct neighborhoods has to offer. Which neighborhood should she visit next? Let her know at [email protected]. 

Milwaukee’s Oakland Avenue starts near Brady Street and stretches two miles north into Shorewood. Neighborhoods in the area include Cambridge Woods, Murray Hill, Riverside Park and the University of Wisconsin-Milwaukee campus.

The area is bordered to the west by the Milwaukee River, with the Oak Leaf Trail stretching alongside, offering a tucked-away path for walkers, runners and bikers.

With its location so close to UW-Milwaukee, Oakland Avenue is home to loads of convenience and fast-food chains. But the walkable neighborhood has so much more to offer, with cozy date-night spots tucked into sleepy, tree-lined streets and beloved institutions that have served students and longtime residents for decades.

Here are just a few of the best places to eat near Oakland Avenue on the east side.

For date night: The Original

I’ve been telling anyone within earshot about this cozy corner spot since I first visited not long after it opened in 2017. Yes, I miss its predecessor, Red Dot (and its poutine), but The Original, 2498 N. Barlett Ave., carries on the friendly neighborhood vibe with a little more refinement.

There’s a cozy ambiance to the dimly lit space, with a throwback aesthetic in details like a tin-paneled ceiling, antique decor and vintage art. Jazzy music gives the whole space a speakeasy-like vibe.

The menu is small but inventive, divided into small and large plates. The dishes swap out seasonally, but you’ll find elevated new-American fare like seafood risotto with tender scallops, lobster and shrimp; pan-seared duck breast; pork and veal meatballs with gnocchi; and hanger steak with house-made chips and dip. On a recent visit I was wowed by the steamed duck dumplings swimming in a spicy chili oil and miso corn broth — such a pleasantly unexpected combination.

The bar is the showpiece of the restaurant, a glowing beauty with vintage charm. But what the bar produces is even more special. Its excellent cocktail menu features expertly concocted classics like a smooth sazarac, puckery penicillin and a beautifully balanced boulevardier.

You’ll have plenty of time to linger over cocktails at this relaxed space that puts an emphasis on its customers’ comfort, with attentive but not aggressive service and an atmosphere that makes it easy to settle into your seat.

For patio dining: Tess

Although Tess, 2499 N. Bartlett Ave., has been a cornerstone of the neighborhood since 2002 (and located directly across the street from the Original), their picturesque patio feels like a secret garden. The fenced-in space is small but dreamy, with oversized flowerpots and soft string lights that add romantic ambiance to evening dinners. It has all the intimacy and warmth of a friend’s backyard.

The menu has an eclectic, global focus, with seasonally changing dishes with beautiful presentation like Korean barbecue shrimp, crispy fried chicken shawarma and saucy San Francisco cioppino. There’s also a stellar Friday fish fry, with options like panko-breaded lake perch and extra crunchy barramundi, also known as Asian sea bass. It comes with a side of rye bread, crunchy Asian coleslaw and one of the best homemade tartar sauces I’ve ever tried.

While the restaurant shines in the summer when patio season is in full swing, Tess stretches out the season with patio heaters outside and a heated, enclosed section when temperatures really drop. But if you visit after patio season, the small but cozy dining room shares the same intimacy and charm this corner restaurant has dished out for decades.

For casual comfort: Immy’s African Cuisine

Immy Kaggwa has spent years building a loyal following of devotees who’ve grown to love the homestyle African cooking she’s served for 15 years — first from her catering business, then from a food truck, and since April 2022, from her brick-and-mortar counter-service spot at 2847 N. Oakland Ave. near Riverside Park.

Immy’s is a beacon at street festivals, but I love having the option to pop into the restaurant whenever the craving strikes (which is often). The space is so vibrant, with boppy music, a colorful dining room accented by a wall filled with gorgeous woven plateau baskets, and exceptionally friendly service.

It’s also home to some of the most comforting food in the city.

As I recently wrote when I named Immy’s spicy chicken egusi as one of my best bites of September, her cooking is rich and layered, the ultimate antidote to the rainy-day blues. Her stews are only heightened with a side of fufu, the soft and starchy ball of pounded African yam that soaks up sauce like a dream. And the jollof rice? I like to mix it into every dish I order for an extra wallop of spice and flavor.

Immy’s is truly soul-warming food, from the goat curry to smoked jerk chicken to the earthy, tangy side of mixed collard and turnip greens. The restaurant also serves rotating vegan entrees like eggplant peanut stew and spiced chickpea stew with roasted cauliflower and carrots.

For something quick: Shahrazad

Shahrazad, 3133 N. Oakland Ave., has been a beloved pillar of the neighborhood since it opened in 1993, serving Persian-Middle Eastern fare like kababs, shawarma, gyro, koubideh and more.

Last year, Sharazad moved from its original location just a few blocks south (now home to Immy’s) and transformed from a mostly sit-down establishment to a counter-service space. Owner Mohammad Khatibi said the shift in service was a result of the change in dining preferences after the pandemic, and he opted for a more pared-down menu with quicker service.

Although the atmosphere might be more casual, the food’s quality is the same. The pita bread is thick and soft, a hearty base for the char-grilled beef shish kabab or juicy grilled chicken sandwiches. I could drizzle their tangy tahini sauce over everything, and I want to bottle the herb-y lemon and olive oil dressing that gives so much life to all the super-fresh salads on their menu. And the vegan samosas with their thin, crisp filo-dough wrappers are one of my all-time favorite appetizers.

I’m happy Shahrazad exists in any form. Now, their quick-service model makes it easy to pop by for a quick lunch. It even accepts Panther Cash for UW-Milwaukee students and faculty.

For late-night bites: Oakland Gyros

What else needs to be said about this diner-style institution that's been slinging stellar gyros and don’t-sleep-on-them burgers at its original location at 2867 N. Oakland Ave. since 1985?

The gyros live up to the hype, served with a pile of juicy meat (enough to fill two pitas) and a heap of onions and tomatoes. The tzatziki sauce is cool and creamy with a nice tang that takes the edge off all those raw onions. It’s hands down the greatest post-bar grub you can get in the area.

If you’re going there late night, order a side of Greek fries (topped with feta cheese, oregano and lemon), onion rings, or their flaky, comforting spanakopita (spinach pie) to help sop up the night’s excesses, and thank me in the morning.

The restaurant is open until 1 a.m. Sunday through Thursday and 2:30 a.m. Friday and Saturday, and it gets pretty bumping in those late-night hours as bar time approaches. If you don’t want to navigate the crowds, Oakland Gyros offers its full menu through GrubHub or UberEats through closing.

Yes, you can eat here — and eat extremely well — during daylight, too (it opens at 10:30 a.m.), but in a city lacking in late-night eateries, I’m so thankful a place as delicious, affordable and reliable as Oakland Gyros exists.

Rachel Bernhard joined the Journal Sentinel as dining critic in June 2023. She’s been busy exploring the Milwaukee-area food scene to share her favorite finds with readers along the way. Like all Journal Sentinel reporters, she buys all meals, accepts no gifts and is independent of all establishments she covers.

What should she cover next? Contact her at [email protected]. Follow her on Twitter at @rachelbernhard or on Instagram at @rach.eats.mke. 

This article originally appeared on Milwaukee Journal Sentinel: Your guide to restaurants on Milwaukee’s east side near Oakland Avenue