JD! You’re spending part of your vacation in the Cotswolds, and you couldn’t be more welcome. In order to squeeze every drop while visiting this little-known area of England, I’ve compiled a few tips.
Firstly, where to stay? If it’s an authentic working smallholding you want, you could do worse than the Soho Farmhouse, set in 100 acres with horse stables, a cinema and barns with underfloor heating. Your room will be a converted pigsty with cast-iron tubs and curated ducks. You will have a chance to discuss rural life with friendly and knowledgeable countrymen.
If it’s kids’ entertainment you’re after, try nearby Estelle Manor, where your offspring can race around in mini Land Rovers. It’s where all the local kids learn to drive. Premium cabins are a very reasonable $1,500 a night.
From there, it is a short hope to another working farm, the quaintly-named Diddly Squat, owned by a real local “character”, Jeremy Clarkson. He is your kinda guy: a petrolhead, anti-woke, no-nonsense salt of the earth multi-millionaire.
You will undoubtedly bond. You use your outrage to galvanise voters. Clarkson uses it to sell books, TV rights and chilli-flavoured mayonnaise. You will love his fart jokes and his encyclopaedic knowledge of 14th-century sheep taxation.
Understand that Clarkson’s agricultural odyssey is genuinely rooted in the absurd realities of British farming—but it’s also brilliantly edited television. Think The Apprentice meets James Herriot. The show is a love letter to rural life, a middle finger to government overreach, and a sitcom disguised as a documentary.
You will doubtless meet another delightful local, Kaleb Cooper, who works alongside Clarkson. You’ll instantly recognise him as the archetype of the forgotten working man, except that he has 2.9m Instagram followers, which is about a million more than you. See this as a meeting of populist icons. Don’t try to win him over with libertarian homilies or war stories from Senate hearings: he’ll just challenge you to reverse a trailer into a tight gate without taking out a water pump.
Next, you must drop in on Daylesford Organic, where all the locals shop. It is technically a farm in the same sense that the nearby Blenheim estate is a garden. Don’t be put off by the prices, which might be considered a hate crime in Appalachia (organic active manuka honey for only £36 a jar!). Only this is not Appalachia: it’s Aspen with sheep. You’ll love the owner, Lady Bamford, who will acknowledge the trauma in your memoir Hillbilly Elegy, but also wonder if the aesthetic has potential. You can discuss diggers with her old man, the Tory-donor Lord Bamford of JCB. Just don’t mention the £500m tax inquiry that was reportedly launched in 2020—the outcome of which remains unknown.
You may be feeling peckish by now, so where better for a pint and some grub than a local hostelry? May we recommend the Bull Inn in Burford, a 16th-century grade II coaching inn lovingly restored by another real Cotswold “character”, Matthew Freud?
Know that Matthew doesn’t do small talk: he does narrative control. Once married to Elisabeth Murdoch, he will admire your origin story and suggest that he could help you with some strategic rebranding.
His favourite chat-up line to celebrities is to hand over his business card and say, “If you ever wake up in bed next to a dead prostitute, you know who to call.” Don’t take offence: it’s just his shtick.
Next, it will be time to meet the other members of the Chipping Norton set: think the Hamptons, only older, colder and with mud-speckled Defenders and labradors named Beckham.
It is now a slightly marginal but still potent clique of political-media aristocracy that peaked during the Cameron years. These days their power is subtler, more slippery. Do not try to bond over populism. They’ll nod politely, then have you edited out of the group photo. If you meet Rebekah Brooks remember Trump is suing her boss Rupert Murdoch for a cool $10bn. When in doubt, change the subject to the weather.
Do not, on any account, travel south to Oxford; it will simply annoy you. If you think Harvard is bad, just wait until you encounter the real thing, with their obsession with pronouns, unisex toilets and trigger warnings; and woke professors who don’t believe in American exceptionalism. They also have a tiresome obsession with facts. They still speak Latin at dinners and graduations, and when you learn about the ructions over a tiny statue of Cecil Rhodes you’ll just get mad. He was just trying to Make Africa Great Again.
Head north instead to the RSC at Stratford, where you may just catch The Winter’s Tale, a character study in paranoia and power. Or too much of a busman’s holiday? Is there something about Leontes that might resonate—an uncanny capacity for self-destruction, reinvention and spectacular ideological whiplash?
Back in Shakespeare’s day, every female character would have been played by a teenage boy in drag. But thankfully, there is no gender-bending cross-dressing in modern performances. You can relax.
Over at Garsington Opera, things are more fluid, so you should probably give their current production of Fidelio a miss. The vibe includes quite a lot of cross-dressing, tyranny and liberation—though the disguise theme arguably aligns with your own trajectory of self-reinvention from Middletown, Ohio, to Yale Law School, to Maga Trumpworld.
If you were hoping for a bit of shooting, you’re out of luck since partridge and pheasant shooting on estates such as Coombe End or Salperton Park doesn’t start until October. It’s probably just as well. Semi-auto shotguns are frowned on: everyone shoots vintage hand-engraved Purdeys that cost more than a Cadillac. Even the ammo is woke: lead-free and bio-degradable. Do not mention AR-15s. No one knows about the Second Amendment.
A note on clothing. A Maga hat in the Cotswolds would be like turning up at Garsington Opera wearing camo. Barbour, yes. Patagonia, never. Cotswolds outerwear must say: “I could survive a blizzard, but I’m really just popping to the farm shop for some heirloom fennel.”
The trick is to look poor, but in a rich way. In the Cotswolds, wealth is whispered, not shouted. Leave behind anything from Under Armour, North Face, LL Bean, or anything that says “Outlaw and Hillbilly” in League Gothic script. Forget your loafers: wear boots. Mud is a class signifier, but maybe not in the way you imagine.
The locals in the Cotswolds do not know what “pill mills” (that illegally dispense drugs) are, and they’d very much like to keep it that way. If you strike up a conversation in the Bull Inn about intergenerational trauma and opioid dependency, you may be asked to leave. Or, worse still, taken for a Guardian columnist.
In summary: keep your opinions zipped and your nostalgia for Appalachia hidden. When in doubt talk about Europe: the locals share your loathing for it. Remember you’re not in Yoo-S-A! any more. You’re in Clarkson Country, which—odd as it may seem—may be even more confusing.
