Iliana and Anna Regan: Milkweed Inn – These Trees Dream in Technicolor

Michigan’s Upper Peninsula is a wild place, rivaled in its wildness—in my personal experience, if we’re talking North America—by the Canadian Yukon and Alaska. The U.P. is Ernest Hemingway’s turf, Jim Harrison’s (who both seemed to favor the central U.P., which is largely wooded and flat and desolate, especially as US-2 meanders through Blaney Park and Naubinway, or the “Seney Stretch” along 28 just north). But Jim Harrison, in his exquisite Brown Dog, pretty much nailed its confounding appeal: “Some are plain addicted to the north despite its absolute inhospitality.”

But this region remains wild, mostly ungentrified, a place that draws the intrepid tourist, the tough and the endlessly curious—those daredevils and headlong adventurous types looking for a new safari. It takes another sort altogether, though, to up and move there for half the year.

Enter Milkweed Inn, super-lauded passion project of Michelin-starred chef and award-winning author Iliana Regan and her wife Anna, a certified wine expert. While elements of luxury and artisanal culture (the odd boutique hotel, fine dining establishment, winery, etc.) have in recent years sewn themselves into the U.P.’s widespread wilds, none—to my knowledge, and I’m a Yooper—have debuted with such force and critical acclaim as Milkweed. 

Milkweed asserts itself as “a small inn/bnb located within the Hiawatha National Forest,” which is both accurate and not particularly: they can accommodate up to 10 guests among three in-cabin rooms, an Airstream and a wall tent. And these guests dine very well—think locally foraged (by Chef Regan herself) everything, moose tartare, smoked lake trout, fresh nettle pasta with kale pesto, and all manner of unspeakably delicious fare in a setting that is nothing short of magical.

All told, this is basically immersion therapy in the deep woods—akin to a five-star hunting camp, say, but the food’s really fucking good.

Can you tell me about yourselves? Where did you grow up, and what was that like?

Anna Hamlin: I grew up in a college town in Southern Indiana. My parents worked in a restaurant and brewery together. My dad started out as a pizza delivery guy and eventually became COO of the company, called One World Enterprise. They had pizza stores that catered to drunk college students, a brewery and a sit down bistro restaurant. I was entranced by the industry from a young age. I started working at the restaurants as soon as my dad would let me—I was obsessed with all the cool college girls I worked with. My mom was conservative and catholic; my dad, a party animal and an atheist. I guess I kind of took after him because by the time I was 15 I was getting into trouble. My parents moved me to Pennsylvanian to live with my aunt, uncle and their five kids. I wasn’t allowed to talk to anyone from Indiana, or go back until I was 18. I finished high school [in Pennsylvania]. Right after I came back to Indiana, the drugs and alcoholism caught up with my dad—he overdosed and died. I dropped out of college and started working in restaurants a year and a half later. 

Iliana Regan: I grew up in northwest Indiana on a small 10-acre farm. It was quiet, for the most part. Kind, gentle, sweet. Lots of fresh produce, canning and foraging. It was a small farmhouse with a small homestead. My sisters were much older than me but left a huge impression. I miss that place and would do anything to get that time back. I think that’s what I’m searching to create with Milkweed. In a sense I’m trying to come full circle and embrace that childhood feeling of comfort. 

Can you tell me a little about Milkweed Inn?

AH: We bought Milkweed sight unseen. It seemed perfect, but we couldn’t get out to see it in February, so we went ahead and took a leap of faith. It’s a cabin about 45 minutes from the nearest gas station, nine miles down a muddy, bumpy logging road. The cabin is situated on 150 acres, has a riverfront, and untouched land. There’s a town called Wetmore about 10 miles north, but it’s not accessible by car. Ten guests arrive on Friday evening, they meet us at a mini mart in town and caravan in, so no one gets lost. We serve five meals total: a casual dinner on Friday, easy breakfast and lunch on Saturday, tasting menu Saturday evening, and Sunday brunch. In between meals on Saturday, guests go out and do activities, explore the forest, or relax with a book. Cell service is limited. After Sunday brunch, we all caravan back to the mini mart, and people go home. It’s essentially an elaborate sleepover dinner party. We do this every weekend for about six months. 

Are you both very outdoorsy?

AH: I’ve always enjoyed camping but I wouldn’t say I’m super outdoorsy. I like living in the middle of nowhere for half the year and in the city for half. It makes you appreciate the beauty and privacy of the woods and the energy of the city. Iliana and I have done plenty of camping together with our dogs. We also have done a couple of big Airstream trips. I used to do a lot of hiking and trail running when I was younger, but I have arthritis now, and can’t walk for long distances. We also got married at a summer camp. Iliana has much a deeper and more pronounced connection to nature than I do. 

IR: I love being outdoors. I spend every day, most of my day outdoors even when I’m in the city. This is exactly what I wanted. I wanted to be right in the middle of the wild and if you ever visit there you’ll see that’s what we did. Sometimes it’s a little frightening to think of how far out we are. But it’s worth it. 

Iliana, you studied creative writing. Can you talk about your journey from there to here? Do you still write, and in what capacity?

IR: I write every single day. In 2019 my first memoir was long listed for the National Book Award. I have a second memoir on the way, the through-line being foraging. I’m currently writing a third novel and completing the MFAW program at the School of the Art Institute in Chicago.

Any tips on hosting a dinner party at home?

AH: I am more on the guest service side of things so I have definitely picked up some tips for making people feel more comfortable. The biggest point of awkwardness is when guests first arrive. They are in your space, and don’t know where anything is. I always give people a tour immediately. I show them where to put their things, where they are staying/sitting, where the bathroom is, etc. Also, get a beverage in their hands as quickly as possible. We always have snacks out and music playing when people get there. And if you don’t know everyone, pick out a characteristic about them as soon as they tell you their name and say it several times—Jenny: freckles; John: orange Crocs, etc. When dinner is over, it’s nice to say something about the group, and how lovely it is that we can all be together and share a nice meal. I always do a thank you and a toast after the last course is served. 

IR: Clean up as you go. Have your mise en place ready. Cook with your intuition and not with hard recipes. Taste as you go. Trust yourself. 

And, finally, I’m having a date over here Thursday, and I’m making vegan sushi. Any tips/advice?

AH: Be yourself, lots of avocado, and use proper sushi rice. 

IR: Marinated shitake mushrooms in the rolls. Tamago, tempura rapini and sweet potato.