Our drawing of the route, over road and path data from OpenStreetMap. It shows where the walk goes and what it goes through. It is not a survey and not a navigation aid — carry OS Explorer on the hill.
A 12.1-mile linking walk with 250 metres of ascent and five and a quarter hours, climbing gradually out of the town to Gillamoor and its famous Surprise View, crossing to Hutton-le-Hole and returning by Spaunton; the going is field path and green lane, with a dozen stiles and a good deal of winter mud in the low ground. It starts in Kirkbymoorside market place, where parking is free in the Church Street car park, and the Coastliner 840 along the A170 puts you within a few minutes' walk of the start. There is water in the becks at Gillamoor and Hutton-le-Hole, and the green lanes are good running ground for a dog, but sheep graze the greens at both villages and cattle are common in the pasture between, so this is a lead walk with releases rather than the other way round.
A tidy 4.7-mile loop with a gentle 90 metres of ascent, two hours at most, on field edges and plantation tracks north of the town, with one or two gates and a stretch that churns up in winter. Start from the market place in Kirkbymoorside, which has free parking off Crown Square and is on the Moorsbus and the York to Helmsley bus route. The plantations are quiet enough for a decent off-lead run and there is a beck near Cockshot for a drink, but the intervening fields hold sheep and cattle, so lead up at every gate.
Seven and three quarter miles with 250 metres of ascent and about three and a half hours, using the Tabular Hills Walk north-east from the town towards Hutton-le-Hole and returning on the limestone shelf; the ascent comes in short pulls rather than one climb and the ground drains well, which makes this a decent autumn option. It starts from Kirkbymoorside market place with free parking on Church Street, and the town has butchers, a bakery and two pubs with water bowls for the finish. The route crosses several small becks that give a drink, and the wooded stretches are good for a dog with its nose down, but the field sections carry sheep for most of the year and there are stone squeeze stiles that a wide-shouldered dog will not fit through.
A 17th-century coaching inn on Kirkbymoorside's Market Place where dogs are positively celebrated - sausages, biscuits and water bowls are laid on, and meals can be taken with your dog in both the pub and restaurant areas. Dog-friendly bedrooms are available for a one-off charge per stay. A comfortable market-town base midway between Helmsley and Pickering.
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