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  • Helmsley - Gateway to the Moors

    From: £540.00 based on 2 people sharing a twin, or double room.
    Difficulty: Easy-Moderate

    Prices from £270 per person

    This self guided walking holiday is based in the perfect English market town of Helmsley. Situated at the beginning of the Cleveland Way and the Ebor Way, this North Yorkshire market town is steeped in history and has attractions to appeal to all, from a 900 year old castle ruins, 250 year old walled garden to charming tea rooms and inviting inns and much more.

About Our Holidays

Walk Yorkshire walking holidays have been carefully selected to discover the finest scenery and the most pleasant places within the North York Moors.

The breaks are structured so you go at your own pace, take detours to places of interest, and have a break when and where you wish. Our routes will provide plenty of opportunities to take refreshments and at the end of each day a relaxing place to spend the night.

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We had an excellent weekend away with Walk Yorkshire. Kev is very knowledgable and makes the whole experience even more personal!

Mr & Mrs Harvey

We decided to try a new kind of weekend break and discovered Walk Yorkshire. The "Gateway to the Moors" break was a perfect introduction for us and we'll be booking with Kev again very soon! 

Mr & Mrs Davies

Simply amazing! We booked a family gathering/walking holiday with Walk Yorkshire and every stop on the Cleveland Way trail was perfect! Cannot recommend Walk Yorkshire enough! 

The Atkinsons