TODAY’S ride starts at the market town of Stokesley, which is easily accessible by the B1257 from Malton and Helmsley. From York or Easingwold, take the A19 north, then A172 to Stokesley.

Starting from the roundabout at the showground car park, head south, signed for Helmsley and Thirsk. Across bridge and first right onto Station Road, signed Kirkby. Pass under the A172 and out of town.

Continue ahead until a crossroad in Kirkby, where left, signed Broughton (and others). Enjoy good view of the Cleveland Hills along here on your right.

At Great Broughton, go straight over a mini roundabout, now following sign for Ingleby. In just under two miles you pass through old woodlands, marked on OS maps as Dixon’s Plantations. Continue into Ingelby Greenhow village, pass St Andrew’s churchyard on right, and the road curves left up a small climb to a T-junction, where right, signed Battersby.

Just out of the village, the road now falls away and this is where Cleveland Wheelers cycling club hold their annual free wheeling competition. So see how far you can go without pedalling.

The route now snakes through the pretty hamlet of Battersby, and over the Middlesbrough-Whitby railway line at an automated crossing. Take care here. Go right at the next fork, following the sign for Kildale and Commondale. There’s a cafe hidden away in Kildale, which you may wish to save for the return journey.

Continue towards Commondale. Take care on a steep descent over cattle grid, with narrow bridge at bottom, followed by an even steeper 25 per cent climb out on the other side. A long descent to Commondale follows, but beware sheep on the now unfenced road.

At Commondale, there’s a choice of route. I’m on a road bike, so I’m going to keep on Tarmac today. However, if on slightly wider tyres, here’s a diversion which avoids the next climb. Follow a sign south towards the station. With Foul Green farm buildings on your left, and chevrons ahead, turn left onto a marked bridleway, still following a sign for the station. This bridleway will take you some two miles, all the way to the outskirts of Castleton.

Otherwise, climb steeply out of Commondale, (toilets on your left) continuing in the same direction as before, also now signed for Castleton. This is Sandhill Bank (17 per cent).

At the top, pause at T-junction. If you look around very carefully here, you’ll find Shaun the Sheep. I won’t include a photo, as that will give the game away.

Go right at T-junction and descend into Castleton, still being wary of loose sheep. If you’ve followed my bridleway diversion, you’ll emerge near the bottom of this descent, turning right onto the road (downhill).

Pass under the railway, and depending on the time of day, possibly avail yourself of the Eskdale Inn here. I enjoyed a pint of Esk’ale (see what they did there?), by North Yorkshire Brewing, of nearby Pinchinthorpe. Also a very reasonable ham sandwich with chips & salad.

Climb into Castleton and left at T-junction, following this road all the way to Danby. Straight over at the staggered crossroad, in front of the Duke of Wellington, on to Briar Hill, following sign for Lealholm.

There’s a bakery cum tearoom up the grass bank now on your left, where I stopped off on my Tour of Yorkshire ride earlier in the year. Beyond Danby, beware of a steep descent and sharp right bend at the bottom. Just past this is the Moors Centre, with cafe and public toilets should you need them.

Pass under the railway, then sharp right onto a single track road. Unsigned, and looks like a farm road. Cross medieval Duck Bridge, rebuilt in 1717 by local stonemason George Duck, but probably 14th century.

Bear left over the bridge, to climb steeply to the ruins of Danby Castle, once home to Katherine Parr, who became the sixth wife of Henry VIII. Retrace slightly from the castle, but now keep left, maintaining height and following the contour of the hill.

After half a mile, descend into Ainthorpe, passing the Fox and Hounds. Look for a hairpin turn back to the left here, onto Lilac Terrace. Follow this to a gate, which walk round and climb a narrow tarmac path. Pass in front of bungalows at top, where left at T-junction and continue back to Castleton.

Here, keep straight ahead, following the High Street as it climbs steadily upwards, passing the Downe Arms. At the top end of Castleton, watch for the speed de-restriction signs, where turn right, signed Commondale.

Keep descending straight ahead, to cross the narrow Dibble Bridge, and a short but steep climb out again. Watch for the first turn off to the left, and take this handy escape route from the continuing climb, now following sign for Kildale.

A long straight follows, through an area known as Sloethorn Park. Go right at the T-junction, signed Kildale, to climb over Kildale Moor and descend (beware sheep) to pass over the railway again.

A short climb brings you to a cross road on the main Esk Dale road, with Kildale signed left. At Kildale, do stop off at the Glebe Cottage cafe. It can be found just off the route in the direction of the station. Last orders 3.45pm.

From Kildale, retrace back to the start, via Battersby, Ingleby, Great Broughton and Kirkby, all of which are signed. Resist being tempted by a direct sign for Stokesley, as this will take you to quite a busy road for the last few miles.

Date of ride: Monday, August 15, 2016

The map: Ordnance Survey Landranger numbers 93, Middlesbrough, and 94 Whitby & Esk Dale

Cafes: West Green Deli, Stokesley,; Glebe Cottage, Kildale, YO21 2RH (11am - 4pm. Closed Thursday and Friday)

The pub: Eskdale Inn, Station Road, Castleton, YO21 2EU. Tel 01287 660333,

The bike: Dolan Preffisio 2016

Distance: 35 miles

Car parking: Pay and display at Showground, Helmsley Road, Stokesley, TS9 5DP. £2.80 all day. Avoid disc parking in central shopping area.