This is a full day's walk along part of the Cleveland Way, but earlier finishes are possible at Sutton Bank (12 miles) and Kilburn (14 miles). The path is clearly marked and suitable for family groups and school parties. But it is a fine weather walk, as on a bad day the path is exposed to strong winds and driving rain.
Begin at Osmotherley, a fine stone-built Yorkshire village beneath the escarpment of the Hambleton Hills, about a mile east of the A19 Thirsk to Teesside road. Go to the Market Cross and stand on the stone table where John Wesley preached in 1755. Turn your back to the Cross and set off up the alley which lies directly ahead and goes past the Methodist church. This is about the only direction needed on the walk, which is well-marked with Cleveland Way markers.
The walk up to Black Hambleton is not too demanding. Keen geographers will be delighted to meet the glacial overflow channel, containing the Oakdale reservoirs, on the way. Reaching Jenny Brewster's Moor, turn south along the Drove Road. This ancient trackway has been used since earliest times and there is evidence of the impact Neolithic, Bronze and Iron Age peoples made on the landscape.
In the 14th century, the Scots led by Robert the Bruce chased Edward II along this track and defeated him in a battle near or on Sutton Bank. But the route came into its own after the Act of Union, when the Scots began to drive their cattle in large numbers down to the markets in England. Most came between 1800 and 1850 before the railway network began to spread and droving went into decline. Up to 400 cattle made up a drove. They were shod (eight shoes per animal) and most were bound for the markets in York or Malton, although some went as far as London. The droves stopped frequently and the line of the drove was marked by inns. In some ways it must have been like a gigantic pub crawl.
Our walk has four inns on, or near, the route: the Chequers, now a farm, Limekiln House, now a ruin, Dialstone House, now a farm, and the Hambleton Inn, happily still a pub selling excellent Theakston's Ales.
Turn off the Drove Road at the well-named High Paradise farm and continue past Boltby Scar with the Iron Age Fort and a windypit (a type of pothole peculiar to this area) nearby and take in the wonderful views to the west. Near Sutton Bank you will find a blissful view over Goremire Lake, one of Yorkshire's rare natural lakes, formed by the blocking by landslide of yet another glacial overflow channel.
On the eastern side of the path, note the gallops used by the racehorse trainers ( nearby Thirsk has an excellent racecourse). The Hambleton Race Ground had horseracing from 1613 to 1776 and was the most important course in the north.
At Sutton Bank stop and think of Wordsworth or test James Herriot's opinion that the view over Roulston Scar is the best in England and decide whether to push on to Kilburn or to Helmsley.
If you choose Kilburn, follow the escarpment south, watching the gliders soar, and descend via the steps past the White Horse to the village where food and accommodation are available, as well as the workshop of oak furniture-maker Robert Thompson.
If Helmsley, then seek out the Cleveland Way route to Cold Kirby, a truly beautiful village; descend via Nettledale to the valley of the River Rye. Call in at Rievaulx Abbey (Rivis to the locals). The remains are magnificent, so imagine what it must have looked like in its 12th century heyday. It was the first Cistercian abbey in Yorkshire and was founded in 1131 by Walter L'Espec. It once had 140 monks and 600 lay brothers. Tear yourself away and take the charming footpath to Helmsley. Here you will find a town with something for everyone and a wide range of hotels, BB's and pubs as well as a first rate youth hostel.
Peter Gorring is co-author of Walk This Way - The Pennine Way (Gotham Press)