Slide Into a Booth at Josie’s, Hillcrest’s New Classic American Diner

Hillcrest has a new place to linger over a second cup of coffee. Josie’s is a classic American diner on Cleveland Avenue from San Diego restaurateurs Matthew Sieve and Jeffrey Fink, the team behind Madison on Park, Madi, and Sonny’s Pizza.

It’s the fifth restaurant the pair have opened together, and the most personal one for Sieve. Expect family recipes, house-made pies, and cinnamon rolls in a room made for long breakfasts.

A long marble-topped diner counter lined with burgundy chrome bar stools at Josie's in Hillcrest

Taste a Family Recipe Box From Minnesota

Sieve grew up working alongside his brothers and father at Traveler’s Inn, his family’s century-old diner in Alexandria, Minnesota. His grandparents, Ben and Helen, ran it for decades. That’s where he fell in love with the restaurant business.

The new diner is named for Josie Holleran, Grandma Helen’s aunt. According to the family memoir, she started washing dishes in a local café at five years old, standing on empty peach crates to reach the sink.

“We’re drawing from recipes, routines, and values that have been part of my family for generations,” says Sieve. “No shortcuts. No ego. Just doing things the right way, every day.”

Order Swedish Meatballs, Pie, and Sour Cherry Pancakes

Breakfast runs from The Diner Breakfast ($15.99) and biscuits and gravy to sour cherry ricotta pancakes and a Northwoods omelet with wild rice and sausage. At lunch, Grandma Helen’s Swedish meatballs come with mashed potatoes and lingonberry sauce, next to a walleye fry and a Reuben on NY corn rye.

Eating lighter? There are smaller plates, high-protein dishes, and a build-your-own bowl ($17.99). The bakery case holds apple and strawberry-rhubarb pie, cinnamon rolls, and scones, baked fresh daily.

A slice of pie on a metal plate next to a latte, salt and pepper shakers, and a newspaper on a red diner table at Josie's

Weekdays come with a deal for each day:

Monday: $1 drip coffee
Tuesday: $9.99 Diner Breakfast
Wednesday: $10.99 ham and cheese, garden, or Denver omelet
Thursday: $1 buttermilk pancake with a breakfast entrée
Friday: $5 mimosas

Grab a Booth, a Counter Stool, or the Photobooth

The room seats about 175, with upholstered booths framed by curved wood, chrome bar stools, café curtains, and glowing glass pendants. Subtle Art Deco touches run throughout, and there’s a photobooth for a little fun.

Josie’s serves breakfast and lunch every day. Dinner starts Thursday, November 26, from 4 PM to 9 PM daily, and the coffee bar will stay open until 9 PM.