4 days, 3 nights in Highlands and Cashiers
Travelogue + breaking down the mystique of a wealthy N.C. enclave
Last week I finally traveled to an enclave in western NC where I’ve been wanting to go for ages: the mountain towns of Highlands and Cashiers (pronounced CASH-ers).
If you’re unfamiliar with either of these spots, it’s no surprise…they exude IYKYK energy.
Wealthy old money southerners and their families have been summering here for decades, and they decamp precisely for the under the radar, low-key vibes.
I may also refer to the towns herein as one unit, because they’re only 20 minutes apart, and if you visit one you’re likely to visit the other.
Usually, when one mentions western NC, Asheville gets the notoriety because of its food and arts, decidedly bohemian feel, and the Biltmore Estate.
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But just that extra push southwest (85 miles and 1.5 hours further to be exact) and Asheville feels extra crunchy when compared to the ilk of Highlands and Cashiers.
Here, I presume the locals are quite happy with less attention and fewer press mentions.
I hear the post-Covid crowds drew even more attention to the area and with them, traffic during peak hours, clogging single-lane highways, which I experienced.
My first impression—judging from the manicured landscapes and how neat and tidy everything was—was that I was visiting the country version of the Hamptons…
But in the forest, and with way more gated country club communities.
In Palm Beach, grandiose houses still peek out from behind tall, perfectly angular hedges.
In the Hamptons, even the biggest homes are on plain view and often steps from main roads.
Not so here…the multi-million dollar homes in Highlands and Cashiers are perfectly tucked away and completely out of sight, safeguarded by entrance gates—themselves set back among lush and leafy forests.
If I know anything about these kinds of communities it’s this: a beautiful and safe bubble, packed to the hilt with amenities and no reason to leave, lest you or your guests crave non-resort food, an occasional grocery or home item (more on that later), or just want to see locals and more people, or even different kinds of people.
I’ll be honest, I was the only Asian person I saw in town. For context, I saw a person on reddit said “here, you can’t pick your politics or religion.”
Also, the towns’ proximity to 3 state lines (Georgia, South Carolina, and North Carolina) attracts a larger swath of the American south.
We counted plates with large contingents from Texas, Florida, South Carolina, Tennessee, and Georgia—more than NC!
Here’s my travelogue of Highlands and Cashiers in North Carolina.
Where we stayed
We stayed in a brand new 2 bed, 2 bath modern AirBnb cottage, a short drive from the Silver Run Trail in Cashiers.
Where we ate
Las Margaritas: The fajitas were sizzling, the frozen piña colada had the obligatory cherry and even whipped cream on top. The service was gracious, and it was one of the few restaurants in Cashiers open past 8pm on a weeknight
On the Side (BBQ): Attached to the Cashiers Farmers Market (more brick & mortar grocery store than traditional farmers market) the beef brisket sandwich was delicious; large, tender slices with a soft bun—what’s not to like? The lunch combo comes with chips and a drink; I got my usual unsweet iced tea with lemon, and it didn’t disappoint
Oak Steakhouse: At the back of Skyline Lodge in Highlands, I was excited for a finer dining experience. As is the case with most of my meals these days since becoming a food writer, it’s hard to find a restaurant where everything is delicious.
My Bolognese was on the too-creamy side, but the homemade pasta was chewy and al dente. The steak frites was an adequate 5 oz. steak and lots of fries, almost too many fries. The highlight of the dinner was the pineapple upside down cake, rare to see on a dessert menuSlab Town Pizza: As a decade-long New Yorker, I take my pizza seriously.
Slab Town claims to offer a New York style pizza, and while it satisfies a hankering, the crust was a little floppy and soggy toward the middle. The sauce wasn’t all that flavorful, either.
That said, it meets the criteria for an easy, decently priced meal, and I think families come here for the local camaraderie, though we (and many others) didn’t anticipate the many screaming children on the loose in the cornhole quad area, who nearly bonked several patrons in the head with plastic play swordsBuck’s Coffee Shop: The coffee and sausage and egg sammie were piping hot and delish. The rustic interior is spacious, welcoming, and bustling. At one point I ventured to the merch area but was dismayed to find so few items from local artisans; a beautiful toile apron was not local-made, but Made in India
Where we ventured
Boutiques
The antique and home decor shops here are interesting.
Most things I saw were brought in from buying trips overseas and estate sales outside of the towns.
I can imagine it’s hard to cater to local vs. tourist tastes and balancing local vs. domestic or imported goods.
That said, if you’re in the market for old European antiques, then you’re in the right place:
Josephine’s Emporium: wooden oblong tabletops, lighting, vintage art, maps, framing, tableware, furniture, oddities—this place has it all with most items sourced from Belgium and France
Reclamations: An assembly of old and really old things, from rusty antique screwdrivers to tea sets, wooden golf clubs, and many garden items. A separate tented area offers custom and new furniture (uninspired) designs
Objet d’Art: Art and gifts, there were these beautiful Parisian bowls with fruit and flowers kind of molded inside glass
Vivace: Popped into this women’s clothing boutique and saw southern designer Carolina Gidiere signing copies of her new book, A Life in Good Taste (Rizzoli). At first I thought she was a local designer but she’s from Alabama
Clothing boutiques: We skipped these because we didn’t really need any new clothes for hiking or daily wear; plus we’re not really the Peter Millar crowd
Main streets
There’s not really a Cashiers “main street” per se, aside from the “farmers market” in the main thoroughfare intersection.
Highlands on the other hand has a more distinct main street set in a loop, where you can venture off into retail boutiques (again, selling the likes of Peter Millar), or amble among shops like Oakleaf Flower & Garden, where you’ll even see a Japanese torii in the garden behind.
There was generally more activity in Highlands; there was an evening event at the trendy Highlander Mountain House with with most diverse and young group we saw all weekend, sipping wine on the outdoors terrace, likely for an event
Where we adventured
Hikes, trails, waterfalls
The many hikes, trails, waterfalls, and even swimming holes bordering the Nantahala Forest area were my favorite parts of this trip.
It’s like mother nature knew exactly how to discretely place these spots as rewards for short and long hikes.
Silver Run Falls Trail: Easy to access, easy to enjoy. And definitely worth the natural cold plunge
Bridal Veil Falls: Directly off the road, you can walk right behind this wispy, stunning waterfall
Whiteside Mountain Trail: A challenging hike up for panoramic views, easy decline down
Wildcat Branch Falls: On the drive back to Charlotte, this easy, rewarding loop hike offered 3 waterfalls: 2 in front and 1 massive one at the end
I’d love to return to this special area of western NC.
It’s quiet, peaceful, and the outdoor activities are the biggest draw. Maybe again before the end of summer!
More from the Shindy-verse
📺 Shows I’m watching
The Gilded Age (on HBO) is back and I’m tuned in. I love love love everything about this period in American history: the fashion, industry, innovation, and the ridiculous social standards in New York City. If you’re a fan of Julian Fellowes (Downtown Abbey, Gosford Park), then season 3 portends a delightful, dramatic, scandalous time ahead
Still watching the forever trainwreck of And Just Like That… on
MaxHBO.
📚 Books I’m reading
The Ride of a Lifetime: Lessons Learned from 15 Years as CEO of the Walt Disney Company, by Bob Iger
After many nights of unwinding with this book at my bedside, I finally finished this one. I don’t typically like non-fiction for nighttime relaxation, but his stories read like fiction; his special friendship and retellings of working with powerhouse creatives like David Lynch and Steve Jobs provide an insight into what working with these two men was like: strong-willed and unyielding, and passionate about the process/product.
Toward the end are his list of leadership lessons; while there’s nothing new here (be decent to people, strive for excellence, own up to mistakes), to see them in his words was fun.
✅ Things I’m doing
I’m building a new AI-based web-app in public, as part of a Lovable Shipped competition, a 6-week cohort of lectures and weekly challenges to produce a fully-functioning site at the end of the program. Once I have a working prototype, I’ll share it here for you to tinker with!
What about you?
Where have you kicked off your summer adventures? I’d love to know! Reply or comment and please ❤️ at top or bottom if you enjoyed this week’s letter.
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Until next time,
Shindy
On Instagram + TikTok
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I love every one of your fashion ensembles; it’s awesome that you include them. You even make hiking 🥾look so cool! You must be a master packer. 🥰🥰
Mr. Bean is a lucky 🍀 little boy!!!!
🩷💚🩷🩷🩷🩷🩷🩷🩷🩷💚🩷
Loved visiting Highlands on occasion when I was living in Atlanta, beautiful drives there and back. Highlands Bar and Grill was a stellar experience