Pretty North Yorkshire market town like breath of fresh air

Helmsley, situated between Pickering and Thirsk, is supposedly somewhere “everyone should visit at least once in their lifetime” – so let’s find out why.

Visit North Yorkshire reveals: “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.”

@the.yorkshireman One of the prettiest towns in Yorkshire ❤️ Helmsley 📍 #northyorkshire #helmsley #northyorkmoors #northyorkmoorsnationalpark ♬ Romantique (from "En Cas De Malheur", 1958) - René Cloërec

Even TikTok travel star The Yorkshireman recently hailed it the “most picturesque” market town in a video.

Is Helmsley worth visiting?

Helmsley is described as the “perfect destination” for those who love the outdoors, with a vast number of walking and cycling routes through the North York Moors National Park (which is on its doorstep).

Visit Yorkshire adds: “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.”

'The castle’s impressive stonework defences include the tall, keep-like east tower' (Image: Tripadvisor) However, one of the most standout features of Helmsley is its castle, which is said to offer “fine views”, so what’s the history behind it?

“Helmsley Castle was in turn a formidable medieval fortress, an Elizabethan mansion, a besieged Civil War stronghold and a Georgian romantic ruin,” explains English Heritage.

“The castle’s impressive stonework defences include the tall, keep-like east tower, which still dominates Helmsley”.

Residents and tourists can stroll around the castle’s “spectacular” double banks and ditches to see the picturesque surroundings of the exterior and the neighbouring parkland, as well as the chance to spot wildflowers and wildlife.

English Heritage continues: “The castle’s west range was converted into an Elizabethan mansion, and some of its fine timber panelling and plasterwork has been conserved. Displays explore life in the castle through five centuries of war and peace.”

Someone who recently visited the castle wrote on Tripadvisor: “Visited the English Heritage site at Helmsley Castle. Given the castle looks like a ruin, was very pleasantly surprised with what we found.

“Lots of rooms as well as ruins to visit, with very informative and well placed information boards dotted around giving the full history and many uses of this grand old castle.

"Situated in wonderful Helmsley right next to the stunning walled garden, I would highly recommend a visit.”

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For those who fancy exploring Helmsley at a more leisurely pace, visitors can “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.”

Plus, the market town has many independent shops and boutiques such as Holme Lea Country Interiors and many welcoming cafés, bakeries, delis, pubs and restaurants – have you been to The Vinehouse Café?

There’s also plenty to choose from when it comes to accommodation, if you want to spend more time in Helmsley than just a quick day trip (think cosy cottages and spa hotels).