'Rocco knows that the four-hours-on, two-hours-off routine of an Atlantic crossing is nothing to the sleep deprivation of Cowes Week': A spotter's guide to the Season

As hats and morning coats are brushed off, picnic hampers are packed and shoes are polished, we pick some of our favourite characters from the Season's milieu.

A rowing eight glides past a bank of spectators at the Henley Royal Regatta
(Image credit: Michael Steele/Getty Images)

The Dowager Countess

Illustration of a gazebo blowing away in the wind at royal ascot

During the five days of the Royal Meeting, racegoers consume about 220,000 finger sandwiches and 65,000 bottles of Champagne .

(Image credit: David Stoten)

Although now advanced in years, Serena considers her annual visit to the Royal Enclosure at Ascot as essential as Christmas. It has taken her nearly two decades to come to terms with the new grandstand, but even she has to admit the escalators do make things easier in her dotage, especially after a Bollinger-boosted picnic. She finds the name badges incredibly useful when she can’t remember what those people they met in Spain are called, although she has never got used to the idea of men, particularly ones she doesn’t really know, looking intently at her, admittedly ample, bosom. The older the man, the worse the eyesight, the more lingering the hard stare.

She hankers after that time she and her late husband were invited by His Majesty’s Representative to lunch in his box, and she was charmed by a man called Rio, who seemed to know more about football than racing, but was giving a prize nevertheless and looked splendid in a top hat.

Her grandson’s racing tips are always enthusiastically communicated, if rarely fiscally sound, although the horses Serena really likes to watch are the ones in the Royal Procession as the carriages make their way down the racecourse. Rupert Uloth

The Hay veterans

A couple chats with another couple on a sunny day at the Hay festival

Hay-on-Wye, which is home to 28 second-hand bookshops, is twinned with Timbuktu in Mali.

(Image credit: David Stoten)

Before he went freelance as a literary PR, Tom was a Penguin publicist, so he has been coming to Hay for years. When they first got together, Stuart, who runs a cheese shop in Bloomsbury, thought a weekend at the world’s most famous book festival sounded jolly. Tom quickly disabused him of this notion: going to Hay is not unlike going to war, specifically the First World War, in that there is a lot of mud and everyone wants to kill each other.

They stay in a draughty farmhouse a 15-minute drive away: the owner, Mrs Davies, waves them off each morning with a picnic of homemade quiche and Welsh cakes. As Stuart has been put on Mounjaro by his GP, he reluctantly gives most of his lunch to Tom, although he does sneak in a scoop of blackberry-ripple ice cream from Shepherds. Eschewing the digital programme so as not to be hostage to the wifi, Tom gets them printed programmes, which he attacks with highlighters and places in plastic wallets. They both have tote bags: Tom’s is from Daunt Books, Stuart’s hopefully advertises his shop.

There’s so much to see that no breaks are allowed; thanks to Tom’s connections, they secure front-row seats for Zadie Smith and Margaret Atwood and invitations to all the after-parties. Tom is in his element at these, trading publishing gossip with agents and knocking back the Cloudy Bay sauvignon blanc. Stuart, nursing an alcohol-free beer as designated driver, wonders whether there are any Welsh cakes left in Mrs Davies’s larder. Emma Hughes

The schoolboy rower’s squeeze

A group of strong young men carry a boat with a woman on top

The Henley course is 1 mile 550 yards (2,112 metres) long, which is longer than the standard 2,000-metre course used in most other regattas.

(Image credit: David Stoten)

Poppy thought (and hoped) it was a rock festival when new boyfriend Jack first invited her to join his parents for Henley. If she had known it was a regular parade of simultaneously bulging male biceps she would have been even more enthusiastic. Correctly attired for the Stewards’ Enclosure in a long flowing dress below the knee, it is, however, unfortunate that, by the time Jack’s Eton eight heaves into view, Poppy’s eyes have become decidedly misty after repeatedly accepting glasses of Champagne from men in a visual cacophony of brightly striped blazers, some of whom she knows.

Jack’s father, a member of the Cambridge eight in 1984, insists they go to the Leander Club to watch the teams ‘boat’, a journey that Poppy only completes after stumbling into an official she later learns won an Olympic gold in 1996. His crucial job on Finals day is to track the Princess Grace Challenge Cup, awarded to the now exuberant women’s quadruple sculls, before it disappears into a mêlée or, worse still, the Thames.

Reunited with Jack at last, Poppy develops a second wind for the after-party on Saturday night when schoolboys, university girls and Olympic heroes from across the world all join up for the traditional celebration in the centre of Henley town, an evening when Jack’s father, Poppy is relieved to note, is ensconced at the bar of the Leander Club fully distracted by his cerise sock-wearing former crew mates. RU

The former tennis prodigy

A general view over Centre Court as Jannik Sinner of Italy plays a forehand against Novak Djokovic of Serbia

An almighty 55,000 Slazenger tennis balls are used during The Championships period.

(Image credit: Hannah Peters/Getty Images)

The first fortnight in July is bittersweet for Boris. When he was born in 1985, his parents named him after the young Becker, who had just won his first title, hoping that their son might emulate the German’s heroics one day. He did make it to the quarter-finals of junior Wimbledon, but this was not enough to secure membership of the highly exclusive All England Tennis & Croquet Club. Like everyone else, he has to enter the online ballot for tickets, although his ageing mother still cannot understand why he doesn’t simply send in a stamped addressed envelope like she always did.

His job as a country solicitor is fairly humdrum, although it was a thrill last year when a new client turned out to have debenture seats; Boris is keeping his fingers crossed that successfully expunging a footpath across the hedge funder’s field by use of an obscure bye-law will secure an invitation this year.

He regularly plays tennis with his wife, Anna, at Rye Lawn Tennis Club and she loves the annual outing, dressing up in her floral ME+EM dress with a denim jacket and little plimsolls, a topped-up tan, blonded hair and expensive sunglasses. He was mortified when the umpire admonished them for their exploding Champagne cork that landed in the tram lines on Centre Court last year and has made a vow to stick to jugs of Pimm’s instead. They could go by car and park in one of the nearby private driveways, although Boris resents the fact that one acquaintance of his makes enough money this way for an annual Mauritius holiday. As if the strawberries aren’t expensive enough.

The Glyndebourne Under 30s member

By the time Francesca’s parents were her age they had a four-bedroom house in Wandsworth, two children and a dog. Francesca has none of these things — but she does have a Glyndebourne Under 30s membership, which is now freighted with all her hopes for upper-middle-class adulthood.

In preparation for Don Giovanni, to which she has invited five friends via an increasingly passive-aggressive Whatsapp group, she has bought a second-hand Edwardian-style hamper on wheels off eBay and stayed up until 3am baking her own pastry cases for the canapés.

'The quintessential English country-house opera’s story began in 1920, when John Christie, owner of the Glyndebourne estate, asked Edmond Warre to build him an organ room. After falling in love with a soprano, Audrey Mildmay, whom he met at one of the recitals he hosted there, Christie and his new wife founded the festival in 1934'

Things get off to a bad start when one of the party misses the train from London Victoria to Glynde and the wheeled hamper gets stuck in the aisle. Francesca’s spirits lift when the cork on the first bottle of Champagne is popped, then plummet when everyone turns out to be much more enthusiastic about the bag of Doritos a friend has smuggled in than her canapés. She fumes through the first act and nearly explodes when they all come out for the interval and find another group sitting at the Upper Circle table she specifically reserved.

She proceeds to get very drunk and, from that point onwards, has a much better time, even when one of the hamper’s wheels falls off when they all have to run for the last bus back to Glynde station. EH

The undergraduate crew member

Even before it begins, Rocco knows that the four-hours-on, two-hours-off routine of an Atlantic crossing is nothing to the sleep deprivation of Cowes Week, with its days of fresh sea air crewing on a J70 segueing seamlessly into the parties that rage like Force 10 gales all week. Newcastle freshers’ week has nothing on the Thursday-night pub crawl through Cowes.

It’s always a panic when his uncle invites him to the Royal Yacht Squadron Ball after-party — as he rifles through his sail bag for his crumpled dinner jacket to replace his deck shoes, shorts and Henri-Lloyd sailing jacket — but it would be a pity to miss out, especially on the espresso martinis. He also makes a point of attending the Mount Gay Rum party, the best chance of securing one of its caps with the year emblazoned on the front and as sought after as any sailing trophy. His godfather’s 1989 one, with its red faded to dusky pink by years of salt water, is held in reverence by young and old sea dogs alike.

It will be the 200th anniversary of Cowes Week this year and Rocco is looking forward to the puff of smoke and the loud report from the ancient cannon that start the races from the castle of the Royal Yacht Squadron and the sight of yachts of all sizes and shapes slicing through the Solent. At night, he will probably sleep the few hours available on the boat to remain in the thick of the action, but he is hoping for romantic pyrotechnics with the spirited blonde working at the marina, who has the added bonus of access to a decent shower. RU

The Wilderness glampers

Illustration of a couple outside a shpeherd's hut at a festival in the rain

Cornbury Park, home of Wilderness festival, is mentioned in the Domesday Book. In the 17th century, its then owner, the Earl of Danby, gave several acres of parkland to the University of Oxford, to be turned into a physic garden.

(Image credit: David Stoten)

It all sounded so promising: four nights at the country’s coolest festival, sleeping in a luxury shepherd’s hut. Now the twins are old enough to stay with their grandparents, Heather and Hamish decided to splash out on ‘glamping’ tickets for Wilderness; Heather, who has never been to a festival before, got a blow-dry to last her for the weekend.

The rose-tinted spectacles come off quickly: in the drizzle, the shepherd’s hut looks like something from The Great Escape. Still, the first evening is fun, with Basement Jaxx on the main stage, and they drink enough spicy margaritas to pass out. Heather comes to with her teeth chattering — she hadn’t realised the huts would be unheated — and finds the rain has become torrential. She and Hamish, who keeps making annoying jokes about them being on a Duke of Edinburgh expedition, spend the day shivering in the talks tent and trekking miles to use the ‘posh portaloos’.

There’s a nice long-table banquet cooked by a celebrity chef, but then it turns out the hut next door to theirs has been booked by some rowdy doctors intent on reliving their 1997 lads’ trip to Ibiza. Heather wakes in the small hours to find Hamish has gone with them to a rave in the valley.

Standing in the rain-lashed coffee queue the next morning as he sleeps it off, she gets wind of a bedroom going at a smart gastropub in the village. An hour later, she is sobbing with relief under its hot shower, having performed a Great Escape of her own. EH


Emma Hughes lives in London and has spent the past 15 years writing for publications including the Guardian, the Telegraph, the Evening Standard, Waitrose Food, British Vogue and Condé Nast Traveller. Currently Country Life's Acting Assistant Features Editor and its London Life restaurant columnist, if she isn't tapping away at a keyboard she's probably taking something out of the oven (or eating it).