I’ll never forget the drive up to Scarborough for my three-day jaunt at Woodside – a cosy little cottage tucked away in the heart of town. The satnav had me convinced I was nearly there, but no, it decided to play silly buggers and sent me on a wild goose chase down a one-way street that wasn’t. I ended up in a dead end, nose-to-bumper with a rusty white van, forced to reverse out under the amused gaze of a chap in wellies who looked like he’d stepped out of a 1970s fishing postcard. “New to these parts, love?” he bellowed, with that proper Yorkshire twang. Turned out he was Derek, the local binman, who not only directed me the right way but insisted on a natter about how Scarborough’s one-ways were designed to trap tourists like me. Laughing, I finally pulled up to Woodside, a charming stone cottage with a front garden bursting with wonky gnomes and a sign that read ‘Mind the Steps – They’re Steeper Than Me Nan’s Hills’.

First impressions? Pure magic. The place felt like stepping into someone’s eccentric auntie’s front room – all chintzy cushions, a Rayburn cooker humming away, and a kettle that whistled like it was auditioning for the Proms. But it was the people who truly made arrival day unforgettable. No sooner had I lugged my bag through the creaky gate than Mrs Hargreaves from next door popped over with a plate of her famous rock buns. She’s a wiry septuagenarian with a perm that defies gravity and stories for days. “You from down south, then?” she eyed my London plates suspiciously. Over a cuppa on the doorstep – proper builder’s tea, mind – she regaled me with tales of Scarborough’s heyday, when the beach was alive with kiss-me-quick hats and donkeys called Doris. “Mind you don’t go paddling after dark,” she winked. “The seals come in, cheeky beggars, nicking chips off folk.”

Wandering down to the South Bay promenade for a breath of sea air, I bumped into Madge, the ice cream lady from the van parked by the funicular. She’s got a laugh like a foghorn and arms like a docker from scooping 99s all summer. “First time at Woodside, pet?” she clocked my sandy shoes. We got chatting while I demolished a double nougat – turns out she’s lived here 40 years, seen every fad from roller discos to TikTok influencers clogging up the beach. “Quirky lot we are,” she chuckled, nodding at a bloke in a Hawaiian shirt walking three Jack Russells dressed as pirates. “That’s Terry. Thinks he’s Captain Birdseye. Don’t let him sell you any ‘fresh’ crab – it’s from the Co-op!” Her gossip was gold; Scarborough’s full of characters like that, turning a simple stroll into a comedy sketch.

Back at the cottage that evening, as the sun dipped behind the cliffs, I met Barry, the landlord popping by to check the boiler. He’s a retired trawlerman with tattoos faded like old tattoos and a beard that could hide a family of otters. “Settling in alright?” he grunted, fiddling with pipes. What started as a five-minute fix turned into an hour of yarns about ghost ships off the coast and the time a pod of dolphins photobombed the Lifeboat Day parade. “This town’s got soul, lad,” he said, slapping my back. “Not like them soulless spas in Filey.” His warmth made the place feel like home already.

Sat there later with a pint from the local microbrewery (picked up from the shop round the corner), reflecting on the day, I realised how these chance encounters beat any fancy hotel lobby. In my rush for seaside escapes, I’d forgotten the joy of proper human connection – the kind that leaves you grinning at strangers’ daftness. Woodside wasn’t just a cottage; it was a front-row seat to Scarborough’s beating heart, all through its brilliant, bonkers locals. Can’t wait to go back.