Helmsley Circular Walk

Michael Palmer
8 hours ago
2 min read

I think the walk is about 4 miles...I forgot to turn the app off and left it on when driving!!!

A Brief History of Helmsley

Helmsley, often described as one of Yorkshire’s prettiest market towns, sits at the southern edge of the North York Moors National Park, where the rolling Howardian Hills meet wild heather moorland. Its history stretches back over a thousand years — it was first mentioned in the Domesday Book of 1086 as Elmeslac, meaning “the clearing of the elms.”

During the medieval period, Helmsley grew around its Norman castle, built in the 12th century by Walter l’Espec. The impressive Helmsley Castle remains a defining feature today, managed by English Heritage and open to visitors year-round. The town also prospered as a market centre, with its wide market square and stone-built inns reflecting centuries of trade and rural life.

In the 18th and 19th centuries, Helmsley developed further under the Duncombe family, who built the grand Duncombe Park estate, a baroque mansion surrounded by landscaped parkland that’s now a popular walking area.

What to Expect

Helmsley is the perfect base for exploring Yorkshire’s walking country. From gentle riverside strolls to rugged moorland hikes, there’s something for every kind of walker:

🥾 The Cleveland Way begins in Helmsley, offering a 109-mile National Trail that winds across the North York Moors to Filey Brigg on the coast.
🌿 Rievaulx Abbey Walk – A scenic 6-mile circular walk from Helmsley to the atmospheric ruins of Rievaulx Abbey, through woodland and along the River Rye.
🌳 Duncombe Park & Helmsley Castle Loop – A shorter 2–3-mile loop through parkland, with views of the castle and the town.

Alongside its walking routes, Helmsley is known for its boutique shops, tearooms, traditional pubs, and local food producers, making it a perfect stop on a day out or a walking weekend.

Practical Information

Location: Helmsley, North Yorkshire, YO62
Parking: Ample pay-and-display parking near the market square and castle
Facilities: Cafés, restaurants, pubs, shops, and public toilets
Transport: Regular buses to York, Pickering, and Scarborough
Best Time to Visit: All year round – spring and autumn are especially scenic.

Why Visit

Helmsley blends heritage, charm, and access to the great outdoors like few other Yorkshire towns. With its historic castle, riverside paths, and the start of the Cleveland Way right on its doorstep, it’s a must-visit for anyone who loves walking, history, and traditional Yorkshire hospitality.