If nobody will say it, I will: most restaurant patios are overrated. I know, I know. Nice weather is precious here. You want to eat outside, and that’s fine. But personally? I’m kinda tired. Patios are fine except for when you’re breathing in exhaust from passing cars and shielding your eyes and exposed skin from the sun when it moves beyond the shade of the umbrella. Securing a table is competitive in some places and a form of exile in others. Throw in a bit of weather and you’ve set yourself up to face many an unknown.

I am, however, not opposed to eating outside in general. In fact, eating outside is an animalistic pleasure I consider on par with looking into a fire or swimming naked in a stream. I’m not advocating for indoor dining forever, but maybe for a little more connectivity between the great outdoors and eating. And since the weather is finally agreeable, I decided to explore this concept by eating handhelds in Milwaukee’s most noteworthy urban spaces. The assignment was simple: get a handheld—which I defined as anything consumable and meant to be gripped in your paws—and take it to the nearest park, chew it over in a philosophical manner, and report back. Here’s what I ate and where.

Glorioso’s Milwaukee Muffalatta [sic] @ anywhere on the lake

This Italian institution on the East Side has been peddling old-world specialties, from mortadella to Montepulciano, since 1946. And their sandwich menu is legit. I am not sure why the deli spells the sandwich name this way. My theory is because we are not in New Orleans, so it cannot be labeled a true “muffuletta.” Either way, the Milwaukee Muffalatta contains thinly sliced mortadella, genoa, ham, and provolone folded over a muffuletta mix on a sesame seed hoagie roll. It is slick with oil and sharp with vinegar, crowded with the titular olive salad containing celery, sport peppers, red peppers, and Italian herbs. The oil soaks into the meat and spills off the edges of the roll.

I took this sandwich to McKinley Marina and ate it between the Lakefront Colectivo and the Roundhouse Beer Garden. This was a pretty good choice. You can’t really go wrong eating a sandwich on the Lake Michigan shoreline. Benches and hills and places to sit in the grass are plentiful if you’re willing to trek the short distance from Brady to the parkway. 8/10.

Optional alternatives: Dogg Haus hot dog, La Masa empanadas.

Oscar’s Frozen Custard Patty Melt @ Greenfield Park

I arrived at Oscar’s hungry to the point of disorientation, and ordered the patty melt in a rushed fugue state. Immediately I wished I’d have tacked on an order of onion rings and custard as well, and I waited for my number, stewing in regret and approaching a hangry state that made the edges of the room blur. It felt criminal to drive all the way here and not leave with frozen custard, our city’s pride and joy. Why did I pick this place? Why didn’t I order the special of the month (queso burger)? On the other hand, my bill was under $7 and I was laid off in May.

Getting from Oscar’s to Greenfield Park is not really possible without a car in this part of Milwaukee, despite them being deceptively close to one another on a map. Initially, I wanted this article to include only parks and handhelds that were within walking distance of each other. This proved much more difficult than expected. Most of our loveliest parks are far enough from quality sandwiches to necessitate driving. The city density just is not there. The to-go bag in my car smelled like vanilla custard and I was so mad at myself for not getting one to go. This park was a mile away. Why did I do this?

But as soon as I sat on the park bench beside the lake at Greenfield Park, my mood improved among the steady alarm of red winged blackbirds and contented turtles sunning on a fallen log. The sandwich is a thin patty with melted Swiss cheese and sautéed onions. The bread is heavily buttered and perfectly grilled. When it was gone, I felt so calm. Whether it was the reliably Zen effects of watching water move in green areas, or the soporific potency of bread, meat, and cheese, I started to feel like this assignment wasn’t a total bust. I spaced out for a while on the bench, thinking about how to obtain gainful employment. Would I do this again? I would both eat the sandwich and visit the park again, but maybe not together. 4/10.

Optional alternative: There’s nothing else in this area I feel confident recommending. My only alternative suggestion is just to get more food at Oscar’s.

Paloma Taco Pocket @ Humboldt Park

This is what I had been waiting for. This pairing is the reason I pursued this story in the first place. If you have not had the Paloma Taco Pocket, consider this a sign to level up your handheld game. It’s $13 and massive. A hands-held rather than a hand-held treat. Paloma in Bay View opened in April following the success of their first location. Although I live closer to the flagship Paloma, and Washington Park is high on my list of Good Parks, the Bay View Paloma is open during the lunch hour.

The Taco Pocket is basically a gourmet Crunchwrap Supreme—a burrito wrap folded over a tostada shell piled with lettuce, cheese, tomato, onions, cilantro, and beef. I think this is one instance in which the facsimile is actually better than the prototypical. You can sub out the “gringo beef” for chicken, carnitas, or one of several vegetarian options, but the beef has the same finely ground consistency of its inspiration and a spice mixture that passes, with flying colors, for the real deal.

Humboldt Park is a gem in the summertime. Sitting on the verdant hillside with a gooey hexagonal burrito gripped in both hands, I tried to connect the Taco Pocket experience to all remembered nights with a Crunchwrap Supreme. The CS/Taco Bell version is advertised as plump and layered, with cheese spilling out an a clearly defined cut between the healthy stuff and that finely ground pasty meat seasoned with an explosive mix. But to my memory, the CS always comes out a little too flat, the burrito-to-filling ratio all askance. The tomatoes always seem a little too cold, shocked into coexistence with the cooked meat which, when cooled, starts to hide behind a greasy layer of the Taco Bell mystery spice. On the other hand, the Taco Pocket is hefty and unshy. It is hot the whole way through and generously loaded. If you wish to compare the Crunchwrap Supreme to the Taco Pocket, the Crunchwrap Supreme is like meeting someone superhot but ultimately underwhelming, and the Taco Pocket is like meeting your soul mate. 10/10.

Optional alternatives (although I don’t know why you would): Anything from Vanguard, a slice from Classic Slice, tacos from 7 Estrellas.

SmallPie Handpie @ South Shore Park

I had a flashback to Oscar’s, so I did not make the same mistake twice: I went to SmallPie and ordered a slice of pie with the herbed chicken handpie. Aside from the pies, crafted by Honey Pie, SmallPie claims the handpie as their signature item. They are piled up and falling over each other in the display case like stacks of poker chips anted in a game.

South Shore Park was not crowded on a Tuesday afternoon. Groups of twos and threes gathered on blankets in the grass. A family fed a gaggle of geese at the small beach along the bay. Someone meditated near the water. The wind swung the sailboats on their moorings, and the skyline to the north sparkled in the clear day, showing-off and pretty by this magical body of fresh water by which we are so privileged to live. When the beer garden is open, you don’t really need to trek in outside food to the park.

The handpie was hot and gushing in a buttery crust. I felt the filling-to-crust ratio was a little low, but this could be for structural reasons, since the handpie maintained its croissant-like consistency all the way through. It was nicely herbed with small cubes of chicken, a flaky and toasty exterior, and just the right size for a quick lunch on the run. For dessert I had a slice of the chocolate hazelnut pie. It was a rare miss for me, more pure sugar-forward than mellow and custardy, which would have paired better with a bitter espresso than my pastry and Topo Chico. 7/10.

Optional alternatives: Anything from the South Shore Terrace menu.

Rupena’s Fine Foods Roast Beef Sandwich @ McCarty Park

I have been a Rupena’s customer for a long time. This family-operated grocery store and deli in West Allis is approaching its 100th year in business and is still managed by members of the Rupena family. It maintains a neighborhood deli feel and carries esoteric grocery items not found in bigger stores. Their shining beacon is the butcher counter and the knowledgeable staff behind the cuts. Rupena’s has yet to steer me wrong.

In addition to the house sandwich menu and a build-your-own option, Rupena’s rotates daily specials on a chalkboard at the counter. I visited on a Friday during their fish fry special, but that’s not my beat in this town, so I ordered the Taste of Milwaukee. This roast beef sandwich is served on a flat and crispy ciabatta with an even spread of horseradish cream, melted cheddar and provolone, and coarsely chopped fresh red onions. It is pressed in a panini maker until the ingredients heat and meld and the bread is lightly toasted. As I waited for my sandwich, I hovered over the meat cuts at the butcher section, admiring tenderloin and rump roasts and hefty pork shoulders, familiar main courses at family gatherings in my clan. I stopped to snap a picture of the ticket number specifically for Milwaukee Record.

“Can I help—oh!” A woman walked into my shot.

“Sorry—I’m just taking a picture,” I stammered. “It’s for…it’s a long story,” I said.

“I bet it isn’t,” she replied and grinned. I offered a quick explanation—I’m eating sandwiches for a publication that has made a running joke out of 69 degree days via the Allen Bradley temperature tower. She chuckled.

“Our butcher never changes the number. It’s our inside joke.”

Perfect! I immediately felt more at ease. This was Maria Rupena, after all.

I collected my sandwich and made my way across the street to a cluster of picnic benches at McCarty Park. The grass had been recently mowed, flattening the green expanse and revealing mud traps in the shade. Kids tore around the nearby playground, but the tennis courts and baseball diamonds were still empty. My Taste of Milwaukee sandwich was warm and creamy, the ciabatta crunchy and lightly buttered, the roast beef and cheese nicely intertwined. The park is just okay, at least on the side I found myself on. Eating beside busy Beloit is not super relaxing. 6/10.

Optional alternative: A different Rupena’s sandwich.

At the end of this assignment (which I assigned to myself) I had some thoughts about what I would do differently. Traveling from the origin of the sandwich/handheld to the nearest worthy park was a hassle just to eat one item, so next time I’d order an entire meal or a bigger variety and make sitting in the park a bigger part of my day. I may not have this luxury for long. I’d also bring a friend along. Not for reasons that facilitate my research, but because friends are great and eating alone in a park while taking notes blocked some pure human pleasure from the experience. It also taught me to always keep a blanket in my car, something to toss out on a grassy hillside and dish out a midday meal.

And there ya have it—no patios required!

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About The Author

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Annie Raab has written about visual art and culture for print and online pubs since 2014. She has a BFA in fine art and an MFA in writing, loves pool, cardio, and tiny apples. She lives in Milwaukee, partially on a sailboat.