Drive time:1.5 hours
Distance:70 miles

When I was growing up, my family, much like any self-respecting suburban Chicago residents with free time and an I-Pass, would drive to Sawyer, Michigan, an unincorporated village on Lake Michigan, to spend the weekend at our summer house. That home and the one we later purchased in New Buffalo contained every conceivable rustic-chic nautical decoration. Horseshoe crab shells? We got ’em under glass. Framed map of the Great Lakes? You want the famous lighthouses or the famous shipwrecks? Because we got ’em both. French ceramic decorative chickens? Yes, that too. We’re talking high-octane quaint.

The towns that dot Michigan’s southwestern shore are picturesque as hell. Want a few names? Combine a water feature or a type of tree with literally any other word. Three Oaks. Grand Beach. Union Pier. Boom. Quaint! We’d play in our backyard pool or head to the beach and look for cool rocks. At the end of the day, we’d stuff ourselves into the car and drive to a nearby town to rent a movie at the laundromat–slash–video store or get dessert at the hardware store–slash–ice cream shop. There were any number of improbable mash-up businesses.

So when I was offered an assignment to take a road trip to Harbor Country, as this corner of the state is known, and check out the culinary offerings, I didn’t think twice. Someone was going to pay me to go to what felt like a second hometown to eat my way through the rolling dunes? My boyfriend and I tossed a duffel bag in the trunk and started on the hour-and-a-half drive. About two hours later, we were huddled in the car, frantically scrolling through Yelp trying to find a restaurant that wasn’t closed for the season. Whose bright idea was it to go to a beach town in February?

In the summer, Harbor Country is a different story: bumper-to-bumper busy, the streets full of Illinois plates. We have our reliable standbys from my childhood. My parents would get up extra early, drive to Harbert Swedish Bakery, grab a dozen cake doughnuts, and drive back before my brothers and I were awake. It was as if these delicacies had appeared out of nowhere. Years later, when we revealed to my parents that for a long time we had no idea they were the ones buying the doughnuts, they thought we were idiots.

Sometimes we’d go to Redamak’s, the legendary burger shop in New Buffalo, twice in one day. You will not find aïoli or arugula on these patties. Redamak’s has been open since 1946 but only started serving lettuce and tomatoes with their burgers in 2016. There are 11 different kinds of fries on the menu. And if we were feeling fancy, we’d head to Skip’s for prime rib and Shirley Temples.

So my boyfriend and I were going to enjoy a trip to Harbor Country on our own to discover new and exciting restaurants. We had even done some research and were armed with recommendations from a chef at Granor Farm, a charming farm-to-table restaurant in Three Oaks. Did we go to that farm-to-table restaurant? No. It was closed for the season.

In the course of the trip, we actually became quite efficient at visiting restaurants in the off-season. One person would get out of the car and walk across the gravel parking lot and check if the place was closed. The other would sit in the running car. If the restaurant was open, the one of us in the car would flip off the ignition and join the other inside. If not, that person would fire up Yelp and our list of recommendations to find the next stop. We began to look forward to the quick walk to the doors of closed restaurants and back. It was our only exercise.

Along Red Arrow Highway in Union Pier, we did manage to discover a gem that was open: Whistle Stop Grocery, where I got a matcha latte and my boyfriend got an Americano. The thought of getting a matcha latte in the Harbor Country of my youth was laughable, but here I was, snapping shots of my green drink. We split a buttery glazed doughnut, a blueberry muffin with an impossibly crumbly top, and a cranberry oat bar. All three were baked in-house and all three were delicious. We picked up a bottle of Provence wine, a jar of Michigan black raspberry jam, and a tub of homemade salted caramel sauce. I felt like Ina Garten, y’all.

We soon found a free Harbor Country publication that had a map of Three Oaks. On the back, little snowflakes marked the businesses open during the winter. Perfect! That’s when we discovered that nearly every business on the main drag with a snowflake was closed on Tuesdays, which just so happened to be the day of our trip. I know, I know. But listen. My boyfriend works in retail, and I’m a freelance writer, improv teacher, and event planner. Our overlapping days off are few and far between.

We stopped in a collectibles shop, and the proprietor explained that many of the business owners on the street were “rich people from Chicago,” so they didn’t care too much about being open seven days a week. His words, not mine. Undaunted, we hit up the nearby Journeyman Distillery, one of only a few certified organic distilleries in the country, and its restaurant Staymaker, which uses — oh my — “local ingredients when possible.” Put that on a tote bag. We had a meat and cheese platter and a salad with frizzled prosciutto and chunks of creamy brie, both of which were good. We also shared a whiskey flight at 1 o’clock in the afternoon. There was an option to upgrade any drink with a blood orange ice cube. I have not experienced that level of decadence anywhere, so I splurged and got one in my lemonade.

We had a little time to kill before it was socially acceptable to head to dinner, so we made our way to the outlet mall in Michigan City, Indiana. Can I recommend strolling an outdoor mall in February? It depends on how dedicated you are to the deals. I spent $40 in a Claire’s because I am an adult woman with a credit card.

Once we had worked up an appetite and I had talked my boyfriend out of buying a $1,000 leather jacket at Coach, we headed to New Buffalo for dinner. We ate at the Terrace Room, an Italian spot at the Harbor Grand Hotel decorated with midcentury modern and Frank Lloyd Wright–inspired touches and a view of the lake. If this restaurant were in Chicago, it’d be playing a soundtrack of Miguel and Solange and the table next to us would be influencers and brain surgeons. But in New Buffalo, we were the youngest people in the restaurant by about 35 years. Everyone was wearing a hoodie with the name of another town in Michigan. When it came time to order, we went nuts: Carpaccio, roasted Brussels sprouts with bacon, ravioli with a trio of sauces, and pappardelle Bolognese. The pasta was handmade, and the portions were big and tasty.

It was time for dessert. In the summer, there would be any number of ice cream parlors with lines out the door and my parents would get into an age-old argument about which place was best. My personal favorite is Bubbles in Michigan City. It’s worth the drive, and like the sign on the wall says, “You can’t be upset when you say ‘bubbles!’ ” So we checked Yelp to see what was open after 8 p.m., a big ask in the off-season. Did we go with the best option? I don’t know. Did we go with an option? You bet your bubbles we did.

That option was the Hard Rock Cafe in the Four Winds Casino. It’s like Las Vegas but with way more knotty pine. We shared a stool at a Candy Crush–themed slot machine and lost $10. We drowned our sorrows with molten chocolate cake and a surprisingly good apple strudel under the protection of Jimmy Buffett’s hat. I assume it’s an important rock ’n’ roll artifact, but I don’t listen to dad music.

The sun had set (three hours earlier) and there wasn’t much more for us to conquer in Harbor Country. So we decided to head home. A billboard on the way back to Chicago told us the opening date for Redamak’s and the unofficial early start of beach season: March 1. We’ll plan a little better next time.