Heading Out
Tripping, Hard
I just got back from Edinburgh for three days with the boys, or the lads, if you will. It was a little bit insane, fully squeezed-in, yearly trip, where we abscond from our wives and children to go drink about one hundred pints in 72 hours.
Since we landed, it has become Vintage Autumn. The weather is crispy and wet. The sky is dark at 6. The leaves they are a-changin’.
It is usually about this time I start hunting for upstate weekend getaways.
So below, please find some of my top recs for what to do in the next six weeks, before the holiday sets in and I take you on a tour of Espresso Martinis to drink in Manhattan when you really want that Cheer™. Stay tuned for that. And don’t forget to tell your friends to subscribe. If you do, I’ll buy you a beer, or 100.
In this issue… Upstate but Fancy, Upstate but Not Fancy, For Non-New Yorkers, and a quick shout out to the Boys.
#1: These leaves cost how much?!
Somewhere in the last five years, the price of hotels has gone from somewhat outrageous to completely fucking batshit. Even with the rise of infinite cheap hotel websites, the quality stuff continues to shock and awe as their prices for peak seasons skyrocket.
And yet… we book.
Upstate New York is experiencing a renaissance of fancy hoteliers who have built resorts on the backs of boutique groups like Foster Supply, who originally built a niche in the Western Catskills with places like The DeBruce and Arnold House.
The DeBruce was nice for 2021. It was post-covid, you were just venturing out, it was a cute, $600-a-night-ish-but-hey-we’re-going-out-and-risking-death-so-whatever-let’s-just-go-for-it kind of vibe.
It’s 2025, and we’re no longer in the $600 range upstate. We’re in the $2600 range. You heard me right.
Enter, Wildflower Farms, the Auberge’s answer to how to do upstate right, complete with massive central firepit, curated farm-to-table menu, and literally every sporting dog in the almanac roaming gracefully through the large, central field.
The place is literally covered in wildflowers. It’s got that quasi-communal, we’re all here because we drained our Amex points kind of vibe. Dog and kid friendly, with great merch, great food, and a wine list with at least four DRCs.
The food is great, the ambience is lovely, and it is literally tailor-made for a weekend in the prime fall. Visit the pet sheep! Take your kids for a walk through the woods! Eat delicious twice-cooked squash fresh from the garden. It’s all wildly expensive. You deserve it.
Across the highway, a rival emerges named Inness. We’ve not stayed, so I can’t recommend, but it is less expensive and I’ve heard offers a competitive product.
And apparently there’s the new Soho House coming in Rhinebeck sometime. I’m sure when it’s open, I’ll be there every weekend. Insert my wife’s eyeroll here.
#2: Or you could glamp?
The other thing upstate are these cute little microcabin communities.
Years back we stayed at Postcard (then Getaway), which are tiny little cabins I would definitely not bring a child to. But if you’re a couple on an early date, it is adorable.
They come complete with firepits and easy start logs, marshmallows, and a bathroom with a shower. These are the non-negotiables.
Now there are more of these, and more upscale versions as well - like Gather Greene and Piaule.
Go for a hike!
#3: I don’t live in NYC, can I also please go apple picking?
Sure. Or something like that.
Here are some regional ideas:
LA: Go to Big Bear
Did you know there is a picture perfect autumn village like an hour from LA? And a private lake? And hiking and firepits and trout?!
SF: Go To Napa
My wife just went on a girls’ trip there and spent a day at Stanly Ranch, the Napa cousin of WFF. In her words, “I recommend it.” I tried to get a better quote, but it’s 9:45PM on a Tuesday. She’s asleep.
Midwest: Minneapolis?
Before it gets freezing, this is one of the loveliest places I ever visited. Fun bars, easy to walk, St. Paul rocks.
Florida: I’d just go to the Viceroy in Riviera Maya.
Forget about fall. They have a dude who literally cleans your sunglasses for you while you’re at the beach.
#4: Let’s Hear It For the Boys
Circling back to my Scotland jaunt, I just wanted to share a bit more.
We ate, we drank, we climbed a mountain on the way to the oldest pub in Scotland. We found a bar on a late wander home that we weren’t sure wasn’t something we literally created like it was the Room of Requirement. Our flight home got canceled and we got circumvented and made back up plans that involved trains, buses, and Soho Farmhouse. It all worked out, and I was at the gym at 6:15AM Monday morning, sweating out the scotch, re-adjusting to EST, and reminiscing about castles.
13/10.
See you in two weeks.
Jay