Is Helmsley the Cotswolds in microcosm? The small market town in North Yorkshire might be small, but it has some of the characteristics: it has biscuit-toned, chocolate-box cottages, a star-studded culinary scene, an ancient castle with walled gardens, a notable Cistercian abbey and beautiful country and coastal walks nearby. The town is perfectly placed to explore the rugged Yorkshire coastline, as the starting point for The Cleveland Way National Trail and sits at the edge of the North York Moors National Park – it’s a bucolic base for a wild and wonderful weekend in the countryside.
In 2024, The Good Food Guide named Helmsley and the Howardian Hills the “most exciting food destination” and the title has been retained in 2026. My mother is from Helmsley and I know how passionate locals are about high-quality homegrown produce – there are some incredible places to eat, some that still feel under-the-radar.
There’s no direct train to Helmsley and I would advise travelling by car anyway, because there’s so much to see in the area: Castle Howard and the Howardian Hills are within easy reach (a 20-minute drive), the Kilburn White Horse and its high-up countryscape (a 15-minute drive), Goathland and the purple heather of the moors and the sleepy shores of Sandsend or the higgledy-piggledy streets of Robin Hood’s Bay (both around a 50-minute drive). And if you just want to relax with no big plans, do local walks, eat well and sleep well, you’re onto a winner; I always feel restored after a visit.
Here are my tips for Helmsley and beyond.
Our favourite things to do in Helmsley
See Helmsley Castle and Helmsley Walled Garden
Small but mighty Helmsley Castle and Helmsley Walled Garden are a must. Historically, it has been a medieval fortress, an Elizabethan mansion and a Georgian ruin. My tip: make a pit stop at the lovely walled garden, which was once a filming location for The Secret Garden. Grab a table at indie Vine House Café, where seasonal plates from the garden like asparagus and mint frittata are served with love – the formidable homemade cakes and freshly baked scones are things of beauty.
Address: Castlegate, Helmsley, York YO62 5AB
Website: english-heritage.org.uk; helmsleywalledgarden.org.uk
