Outpost (Newsletter)

Am I an expert in Oktoberfest? No. I’ve been once, drank about 15 beers, and don’t speak a lick of German. So I can’t exactly say I’m the North Star here. What I can say is that the American experience at Oktoberfest is very different from that of a German. They’ve had their reservations for months, years, or even generations, passing them down like family heirlooms. The chances are, you’re like me and were too busy or too naive to get a proper res sorted. I’m here to help.

Happy (almost) end of Negroni Week for those who celebrate. The week is not yet over, so get over to Margot or Dante and drink for a cause. It’s a Friday and by god, it is fall. The green leaves are transforming to a crisp yellow as we speak. This September is lush with restaurant openings, as if we are in a distinctly golden era of new beginnings. But we must not be fools and brush off the old for the new in one sweep.

In Amsterdam, I’m part of a cycling club called Lyka and regularly attend MAAP’s Sunday rides. If you’re a cyclist, there are plenty of options in the Netherlands. It’s easy to access the countryside, and it’s the best way to explore nature quickly. Both groups I mentioned accept visitors, so check them out even if you’re only in the Netherlands for the short term. This is hands down the most stunning ride I’ve ever done.

At 5:15 a.m., I was more awake than I had any right to be. The usual early-morning fog had given way to excitement. We weren’t just going fishing. We were fishing the Derby. I climbed out of the old bed at my parents’ house, grabbed my duffel bag, and hurried outside. At the bottom of the driveway, my father was already packing several large coolers with fresh ice. We loaded them into the back of his white Ford F-150 and, by 5:35, were headed for the dock.

I’m in the middle of a hellish bit of travel, coming from Austin for the week with the Hospitality Cup team (more on that below), followed by a wedding in East Hampton this weekend for two dear friends. Then it’s off to Munich, Berlin & Ireland tomorrow night. It feels insane to even write that, but as a result, we’re going to hit a classic Need, Read & Ate — a throwback to how the newsletter started for those of you who have been here from the beginning.

If you spend enough time in New York City, one’s taste comes down to where they go out to dinner. Your friends talk about how they can’t believe Meredith was able to snag a table at Polo Bar or that James has an extra seat at Carbone if you want to join. Resy, OpenTable, ResX, Beli, Blackbird, inKind, etc. have reoriented our phones around dining out. Reservations have become more than reservations.

Labor Day has come and gone and with it the last vestiges of summer. Since Congress made the holiday official in 1894, the first Monday in September has marked the change of seasonal style. If you’re anything like me, this transitional period always poses a deeply existential styling conundrum: What to wear? What to wear… In this transitional time, we are all a bit lost in the closet, wandering around in a state of seasonal confusion.

Friends, after another long, gin-soaked summer, we have finally slid back into September, and I couldn’t be happier. I’ve always loved the shoulder months, especially the fall. Winter presses inward from the sky, and you can smell the change—leaves and asphalt. Water. In many ways, I see shifting into autumn as a homecoming—a return to routine and rest—and, in the spirit of turning the page, I want to introduce a new Outpost feature for our subscribers: The Ramble.

One of the questions I both get and give is: Where should I go for a first, second, or third date? So I’ve set out to create an encyclopedia of the best date spots, categorized by occasion and location. Over the course of the fall, the Outpost team will bring all paid members a go-to guide. Learn it, live it, love it. Maybe pin it to the fridge. Summer’s over, time to strap in. My first rule is simple: on a first date, you should always play the away game and accommodate her location.

If I told you to name three spices off the top of your head, what would you say? Salt, pepper, and a maybe a third, less ubiquitous option. Cinnamon, perhaps. But if I asked you to describe the origins of each of these household staples—how they were collected, prepared, and who handled them—most people couldn’t get past the grocery store.