Helmsley
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- Helmsley
One of North Yorkshire’s most popular market towns (officially - it won the Great British High Street Award’s best market town category), Helmsley is somewhere everyone should visit at least once in their lifetime. Although if you go once, you are likely to go back time and time again - a visit to this picturesque place, which has so much going on, feels like a breath of fresh air.
Helmsley is a perfect destination for those who love the great outdoors with a wealth of walking and cycling routes through the North York Moors National Park which is on its doorstep. The Discovery Trail showcases local history on an easy loop, while cyclists can enjoy routes like the Helmsley to Rievaulx Abbey ride and the challenging North York Moors Cycleway, passing through heather landscapes and hidden valleys on quieter roads. One of the highlights is the Cleveland Way, a renowned national trail that starts in Helmsley. If you fancy taking a dip to cool off, the town’s open-air pool is a refreshing option in the summer months.
If you prefer a more leisurely pace, take a trip back in time at the town’s castle, admire the stunning blooms and floral arches at the walled garden, marvel at spectacular birds of prey displays at the nearby estate, or wander stunning National Trust sites just outside of town. Take a stroll around and browse the town’s many independent shops and boutiques, savour a bite to eat in the welcoming cafés and bakeries, delicious delis and welcoming pubs and restaurants. When it’s time to rest after a day exploring, choose from a range of quality accommodation from spa hotels to cosy cottages.

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Businesses in Helmsley
Studford Luxury Lodges
Tucked away in a quiet corner of the North York Moors National Park, just… Tucked away in a quiet corner of the North York Moors National Park, just four miles from the market town of Helmsley, these luxurious designer tree…
Holly-Garth Holiday Cottage
Holly-Garth is a superbly equipped 4 star holiday cottage near the centre… Holly-Garth is a superbly equipped 4 star holiday cottage near the centre of the pretty town of Helmsley, on the edge of the North York Moors. We…
Black Swan at Oldstead
The Black Swan at Oldstead is a restaurant with rooms created by the Banks… The Black Swan at Oldstead is a restaurant with rooms created by the Banks family who have lived and farmed around Oldstead for centuries.
The Pheasant Hotel
Beautifully located Country Hotel with award-winning restaurant set in a… Beautifully located Country Hotel with award-winning restaurant set in a quiet village just a couple of miles from the market town of Helmsley.…
Summerfield Farm Holiday Cottage
Summerfield Holiday Cottage is a stone built cottage, which sleeps 4-5. It… Summerfield Holiday Cottage is a stone built cottage, which sleeps 4-5. It is situated on a small, family run, working farm in a peaceful and rural…
Cliff Cottages - Frankel Cottage
The location and surrounding views are breathtaking during all seasons.… The location and surrounding views are breathtaking during all seasons. It’s a very peaceful place despite being so close to the centre of town.
Helmsley Walled Garden
This tranquil and historic five acre garden is beautifully laid out in… This tranquil and historic five acre garden is beautifully laid out in small intimate garden spaces to explore. Enjoy the cool of the foliage border,…
Howardian Hills
Designated a National Landscape, the Howardian Hills cover 77 square miles… Designated a National Landscape, the Howardian Hills cover 77 square miles of woods, farmland and historic parkland.
Events in Helmsley
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The story covers subjects ranging from pantomimes to dreams, how to behave… The story covers subjects ranging from pantomimes to dreams, how to behave in hospitals, small talk, realising his Mum is a northern version of…
I'm not Dorothy, I'm Dot. Like a decimal point. A full stop. Dot.Stroppy… I'm not Dorothy, I'm Dot. Like a decimal point. A full stop. Dot.Stroppy teenager Dot just wants everyone to shut up and leave her alone. Sick of her…
The story covers subjects ranging from pantomimes to dreams, how to behave… The story covers subjects ranging from pantomimes to dreams, how to behave in hospitals, small talk, realising his Mum is a northern version of…