The first time I went to Littlestone-On-Sea, I parked the car, got out – and promptly got straight back in again. I’d driven the 10 minutes from Dungeness, where outsized skies ranged over shingle busy with alien-like plants and designer cabins, and where the strange dry gardens felt like a glimpse into a possible future (one in which we might all be practising horticulture on the moon).
With this incredible scenery front of mind, Littlestone was the ultimate anti-climax. Grey waves pounded steeply shelving stones and a jumble of drab flats and peeling houses lined the road behind.
This would have been a huge disappointment to Sir Robert Perks, the 19th-century politician and property developer who hoped to transform the tiny village into a health resort back in the 1880s. Progress was slow, possibly hampered by the fact that his associate Henry Tubbs, the owner of the local golf club (and builder of the redbrick water tower that still stands proud as the tallest thing on the skyline) was a staunch supporter of the temperance movement.
When grey skies open over Littlestone, thoughts inevitably turn to alcohol – but he saw to it that none was available to visiting golfers. Despite this, Bright Young Things did eventually come. In the interwar years, they put up a flurry of grand holiday homes near Tubbs’s golf club. But soon after that came cheap flights – and Littlestone melted into obscurity once more.
Beyond the village’s striped beach huts where the main road peters out in the direction of Hythe, some of these homes remain. A handful, like the one I passed on the seafront that was cheerfully blasting Frank Sinatra songs from behind a rainbow cloak of washing, seem to be slowly falling into disrepair. Others, set around the grass-verged roads by the golf club, are now the very definition of respectability, their frontages freshly painted and Union Jacks fluttering from their flagpoles.
And now there are signs that Littlestone may soon have another moment in the sun. Since I last visited, modern mansions with cedar cladding and floor-to-ceiling glass have been sprouting up between the old ones. Meanwhile, Harry Cragoe, the hotelier behind the ultra-successful Gallivant hotel in Camber Sands (doubles from £165, B&B), will open a Littlestone outpost in 2024.
He’s picked a winner with the building. The hotel was originally designed as a holiday home for a woman named Margaret Bray by the architect behind Portmeirion, Sir Clough Williams-Ellis. “She mixed in some really interesting circles. She was a really out there, avant-garde lady,” says Cragoe. Legend has it that Noel Coward and members of the Astor family stayed, although actual evidence is thin on the ground.
Standing at a 45-degree angle to the sea as if to distinguish itself from the other buildings on the promenade, the facade is positively Gatsby-esque, if a little faded. But, while revellers in that novel partied hard in Long Island, the most those in Littlestone can currently hope for is a takeaway curry or fish and chips on the concrete sea wall. Even coffee seems impossible to find (unless you count the takeaway Costa machine at the local Spar).
The challenge for Cragoe will be to ensure that visitors in the upstairs bedrooms, from which the views stretch to France on clear days, don’t wish they’d gone that extra few miles and made it across the Channel. With this in mind, there’ll be a Bamford spa, a wood-fired sauna for post-swim warm ups, a dry garden on a grander scale than those in Dungeness and a wine list full of English treasures. “Our plan with Littlestone is to bring back the glamour. It was clearly once a very fashionable holiday destination, particularly for Londoners,” he says.
The golf course, once Littlestone’s biggest selling point, is still a draw too. “If you’re a golfer, Alister MacKenzie is like the Nash of golf designers. He designed Cypress Point and the Augusta course where the Masters is played,” says Cragoe. “He came over to redesign the Club in Littlestone after the war, because the whole area was being used by the military for training and the golf course was churned up. It means there’s a deep connection with the very top golf courses in America. That heritage has perhaps been slightly overshadowed by Rye Golf Course but Littlestone has an amazing history as well”.
If anyone can change Littlestone’s fortunes, Cragoe can. His other hotel did much to boost Camber Sands’s appeal. “My friends thought I was absolutely [deluded] buying that place. It was a rundown roadside motel that was busy for two months with families and empty the rest of the time.”
“Through very hard work, quite a lot of money and a real vision of what we wanted to do, we created something, we think, quite special. Littlestone for us is the logical next step. As a blank canvas it’s far more exciting because [...] you’ve got a really beautiful structure in the most remarkable location”.
His timing is right too. Along the coastal path, a handful of cyclists with cut-glass accents ting their bells for pedestrians to get out of their way in a manner suggestive of London’s canalside pedallers, signalling that there are already weekenders in town. And, if you walk 10 minutes from Cragoe’s building towards St Mary’s Bay, you reach Cabu by the Sea, a collection of posh cabins that’s popular with in-the-know couples and families. When the tide goes out, there’s another surprise too: ripples of sand beyond the pebbles to tempt those who are sniffy about shingle.
As for me, the sun shone on my second visit to Littlestone, turning the water to sequins and sending the faraway hulk of Dungeness power station into hazy relief. The empty beach could never be called pretty but, under the intense blue of a cloudless sky, it was invigoratingly dramatic. I walked back to the beach car park, stopping off at Spar on route to pick up a latte. Then I sat on the promenade and toasted a brighter future.