Week 33 What I Need, Wrote & Ate
Sunday August 24th - Dog Days of Summer
A bit of housekeeping…
Starting September 1, the newsletter goes paid.
The free ride’s over folks - The leaves are starting to fall, the days are getting shorter, and beginning September 1, every other newsletter will be behind a paywall. This wasn’t an easy decision, but a necessary one so let me walk you through it:
Substack’s algorithm favors paid posts.
Outpost is becoming a brand, brands need money. Every dollar from this Substack goes straight into Outpost. That means bigger parties, paid contributions from other talented voices, and more ambitious projects. Doesn’t that sound fun?
Its only fair, Plenty of folks already pay. It’s not right for them to fill the coffers while others ride the coattails…Grass, ass, or cash.
That said—this has never really been about money. I genuinely love writing to you every Sunday.
So here’s my thank-you: for the rest of the summer, you can lock in an annual plan 50% off ($30), the lowest Substack allows. For the cost of a Chipotle date, you’ll get everything Outpost has to offer: city guides, New York tips, discounts, exclusive merch, early event access, and more.
On September 1, the price doubles. Get it while it’s hot, kids.
Need – $300 French Umbrella
Working in real estate for half a decade, every single goodie bag was cold hard cash in the form of a gift card. Old-school bribery thats exstience in this day and age still blows my mind. More often than not, it came with a bottle of liquor and/or an umbrella stamped with the address of whatever sad office building they wanted you to bring your clients to (of which I had none).
As a result, I don’t think I’ve ever owned an umbrella that lasted more than a month—always falling victim to a barstool or hotel lobby with the classic “oh it stopped raining” syndrome after a few cocktails.
That ends today. All of you reading just added your dad’s American Express for an annual subscription to this newsletter, and I’m taking my winnings to Le Parapluie de Cherbourg to buy this incredible work of art… which will inevitably be lost in a month.
Parapluie started as a leather goods company in Cherbourg in the 1800s. Two hundred years later, Charles—the son of a long lineage—is at the helm, building umbrellas tough enough to withstand everything from wind tunnels to knife attacks. Le Parapluie is guaranteed to last a lifetime.
Keep an eye out for a potential Outpost collab.
Wrote: A bonus Recommendation
We’re running long here—consider the intro my “wrote.” Here’s a bonus find (the bonus ones are always better anyway): Guntû – An 18 Cabin Japanese hotel floating on the Seto Inland Sea.
Haven’t you always said you wanted to eat sushi, sweat it out in saunas, and get massages while floating around the islands of Japan on a teak boat? Here you go.
Ate: Litchfield County
I was bouncing around upstate Connecticut all week. Here are the top places I ate:
Arethusa al Tavolo
George Malkemus and Anthony Yurgaitis, president and vice president of Manolo Blahnik (yes, that Manolo Blahnik that makes the stiletto), bought a 375-head dairy farm decades ago. Almost 30 years later, the farm makes the best ice cream and eggnog I’ve ever had. No surprise the farm-to-table restaurant is spectacular. The full story is worth a read.
From the owners of the legendary Troutbeck resort in Amenia, this new hotel deserves a full write-up (not today). The restaurant just opened to guests—food is solid, but the property itself is the real draw. Get a spa day pass next door, unwind, then stay for dinner. If things are looking good, splurge on a room and hang a tie on the door—the hotel’s tongue-in-cheek replacement for “do not disturb” signs. “Just like college dorms”
Dating to the 1950s, this diner has been written up twice by The New York Times—probably because half their editors have second homes nearby. Regardless, the hype is deserved. I grabbed lunch before hitting the antique shops of Millerton. The menu balances basics with twists like kimchi and Mexican. Normally I’d shake my fist at that kind of thing, but Oakhurst nails it. No notes.
More next Monday for a special Labor Day edition. Until then, eat an heirloom and enjoy the last few days of summer.
Cheers,