This letter is brought to you by: the feeling of switching between two movie channels at the commercial break on a hotel TV late at night.
Shelter has returned from summer break. We were in Malibu…and Cape Cod!
(Of the Midwest, to be clear. That’s right: I’m talking about Sheboygan and Door County, Wisconsin.) As we headed northward, I considered how the way I travel has evolved through three distinct phases:
As a kid, my parents would pack as much as possible into the itinerary. We’d rush to every museum exhibit and walking tour we could find, particularly on our many trips to explore sites of the Revolutionary War. There was always the feeling that we had to do it all.
In my 20s, I was lucky to travel professionally as the publisher of a magazine, which gave me a great excuse to be nosy and be invited into spaces with characters no tourist would typically get to meet during their trip: in the Blackfeet Nation in Montana, in the homes of madcap architects in Vermont, onboard lobster boats in Maine, and so on. For several years, I couldn’t travel without being in “reporter mode” — like I wasn’t getting the most out of a trip unless I was telling stories and getting the behind-the-scenes access a publication can provide.
Early in our marriage, my wife remarked that she didn’t know if I’d ever taken a proper vacation in my life. “You’re always either trying to do it all — or filing a story on deadline,” she said. (Ah, the freelance journalist never sleeps.) My wife’s perfect vacation is: good food, cocktail hour, a beach read, and two activities (max) per day. And so I started trying to relax.
These days, I find myself gravitating to small towns on water instead of cities. Places with a few decent restaurants and attractions, but mostly quiet. My approach usually looks like this:
Get oriented with a custom map. Open a million browser tabs and pull in the best leads to a Google map. Not only does this make it easy to get the lay of a new landscape, it allows you to choose your own adventure based on where you find yourself on a given day. At the end of the trip, slim it down to the best stuff you ate, drank, and did — and perhaps a section of things to check out if you return. Here's the one I made from Sheboygan to Door County.
Search place names. You'll learn what people, history, and values give the land its essence — and which Native tribes roamed the grounds you're visiting.
Eat at each of the good restaurants in town (and some of them twice). But spend more time still in the aisles of the local grocer, trying to solve some of the creative cooking challenges posed by an unfamiliar kitchen.
If the region is known for a local delicacy, make it your own. In this case, the week was spent exploring the many secrets and variations of the brandy old fashioned.
Whip up a low-effort zine. If you’re good at drawing, power to you. I am not, so I rely on stickers, pictures, and quotes from the trip. Here’s a simple zine template I’m using with a single piece of paper; I’ll share my progress when it’s done.
Every trip deserves a soundtrack. Source by genre (if the place is known for a specific style), the artist's geographical connection, or perhaps the season. Here’s our playlist for this trip, made in collaboration with friend-of-the-newsletter Lizz Kannenberg, the Audio Baroness (exiled) of Whitefish Bay. From Lizz: “The vibe is ‘Summer afternoon near water, pine trees, with grilled encased meats and cold beverages,’ with a bias towards WI artists.” Editor’s note: There are no finer words in the English language than “encased meats,” my friend. IYKYK.
These thoughts are inspired in large part by a conversation I had with reader Elin R., in which she told me that the magic of traveling (especially with a young child) is that "you get to try on another life; you get to totally vacate your normal habits and housework. You realize that you can live with so much less. One loaf of good bread, one jar of jam, some Kerrygold Irish butter — and Bob's yer uncle."
You can find a “reporter’s notebook” on what we saw this week in Wisconsin at the bottom of this letter, after the links.
away we go.
What makes a Wisconsin supper club a Wisconsin supper club?
By Hannah Kirby for The Milwaukee Journal-Sentinel
Best line: When you step inside, you'll be met with the familiarity and warmness of an up-north cabin, a glimmer of an old Hollywood film — and possibly a mounted deer head or two? Yup, you're at a Wisconsin supper club.
Often, the evening starts with an old fashioned and ends with a grasshopper. You might run into an old buddy or neighbor. You might meet someone who feels like an old buddy or neighbor by evening's end.
Supper clubs are a lot of things. But also, a lot of things they are not.
52 Places to Travel in the U.S. This Year by Nicholas Derenzo for AFAR
Best line: “In celebration of America’s 250th birthday in 2026, we’ve searched the country for the boldest, artsiest, buzziest, friendliest, tastiest, booziest things going on right now. Indigenous art galleries, immigrant-owned barbecue joints, revitalized rivers made for whitewater rafting, new expedition cruise routes, Nordic-themed sauna road trips, retro beach hotels: Here are 52 unique places and experiences that have us ready to book a flight and go explore.”
AI Redefined Their Industries, So This Creative Couple Pivoted and Built a Backup Plan: a Pizzeria by Zoë Sessums for Architectural Digest
My take: I’ve been saying, and remain convinced, that the best defense against AI-induced career loss is hospitality in the meat space.
Best line: “There’s a reason makers are drawn to this part of Maine. It attracts people who want to create things and be part of something—people with that New England pragmatism, even if they aren’t originally from here. It’s a fiercely individualistic place, but also deeply creative. Most of our friends here run small businesses or are artists or musicians. That’s rare in an area this small.
When the space opened up and we talked to the landlord, he mentioned that if they couldn’t find a tenant to continue using the space as a restaurant, he was considering turning it into offices. And that felt off. When we first arrived, the cafe that used to be here hosted events—bingo, trivia, open mic nights—and people showed up. Once that place closed, it felt like the town needed that gathering place. Now, we’re that place.”
The Frank Lloyd Wright Road Trip That Midcentury-Modern Lovers Need to Take by Alex Temblador for Dwell
Best line: “Frank Lloyd Wright once famously said, "Study nature, love nature, stay close to nature. It will never fail you." Now, a self-guided motor trail honoring the visionary architect incorporates this sentiment by piecing together his architectural masterpieces with lovely landscapes in his birthplace and home state: Wisconsin.”
7 Wisconsin shipwrecks you can dive to in the Great Lakes by Claire Reid for The Milwaukee Journal-Sentinel
Best line: The remains of the Empire State, Ida Corning and Oak Leaf are easily accessible to divers, snorkelers, kayakers and even pedestrians at Bullhead Point City Park on the west side of the Sturgeon Bay in Door County. A historic marker provides information about, and points out, the wrecks. The three 19th-century wooden barges were abandoned and burned to the waterline at Bullhead Point in 1931 after there was no longer a use from them due to the Great Depression. The ships were last owned by the Sturgeon Bay Stone Company and used to transport limestone.
According to Wisconsin Shipwrecks, the three shipwrecks sit in zero-to-10 feet of water, very close to shore, and are thus easily visible, especially when the water level is low.
home tour
A Light-Filled Modern Farmhouse in Door County
By Lucy Wang for Dwell
Best line: "Our client, Beth, loves the open farm fields of the area, and this project was in many ways her vision," note the architects, who named the project House for Beth. "They asked for a one-floor retreat with a minimal number of rooms and maximum amount of light and views, so that it would fit into the context of the open fields of Door County."
More Wisconsin ephemera
A reporter’s notepad on what we encountered during our trip up the shore.
Classic American roadtrip fodder:
A cheese castle in Kenosha
The tallest flagpole in the nation in Sheboygan
Tug Ludington, a tugboat involved in the D-Day invasion of Normandy in Kewaunee
The spot where Sputnik crashed in Manitowoc
Goats on the roof of a Swedish restaurant, which you can see on the Goat Cam
A note on supper clubs:
A supper club is a family restaurant that time forgot.
It’s outdated, and that’s the point.
Brandy old-fashioneds are likely to run you $4 a piece, even in 2025.
The relish tray is a must.
This is practically the Michelin Guide of supper clubs.
Names to know:
Milwaukee: derived from the Potawatomi word for “council grounds.”
Sheboygan: from the Chippewa word for “passage between the lakes.”
Manitowoc: from the Menominee word for “place of the spirits.”
Kewaunee: based on a Menominee word for a species of duck, and the site of a Potawatomi village at the time of first European contact.
Porte des Mortes: French for “Door of the Dead” — the name of the channel between the peninsula and Washington, and how Door County got its name.
Influential Wisconsinites:
Georgia O’Keeffe: born in Sun Prairie.
Frank Lloyd Wright: born in Richland Center, later created Taliesin in Spring Green.
John Muir: a resident of Portage.
Harry Houdini: born in Appleton.
William Harley & Arthur Davidson: the motorcyclists, headquartered in Milwaukee.
Seth Putnam is an editor and writer in Chicago. He lives with his wife, son, and daughter in a 1920s home that is the epitome of a work in progress.
"Instructions for living a life: Pay attention. Be astonished. Tell about it." —Mary Oliver