Starting the Wessex Ridgeway in Dorset at Ashmore, the highest village in the county, make your way through woodland and down into the Tarrant Valley. Pass an ancient hidden deer park and use historic smuggling routes that linked the coast to town via Cranborne Chase. Climb the mighty Iron Age hillfort of Hambledon Hill, to then travel down into the valley of the River Stour, passing under the old Somerset and Dorset railway. Finally ascend another Dorset peak of Okeford Hill before finishing the ride at the car park.
Distance – 14 miles/22.5 km
Duration – 4 hours.
Exertion – Completely dependent on fitness. Three hard climbs up out of Stubhampton, Hambledon Hill and Okeford Hill. The terrain can get rough too, and may require dismounting and pushing.
Terrain – Track and road. Can get very muddy after rain. Can become hard, and rutted with tractor tyre tracks and hoof prints during the summer.
Dogs – Be aware of livestock and keep to the countryside code. Not really advised for this ride.
Maps – OS Explorer 118 Shaftesbury and Cranborne Chase, OS Explorer 117 Cerne Abbas and Bere Regis. Also cutting a small corner on OS Explorer 129 Yeovil and Sherborne.
Start – At the pond in Ashmore. (Postcode: SP5 5AF, Grid Reference: ST912178, What Three Words: stealthier.propose.juniors)
Finish – At the parking area at the top of Okeford Hill. (Postcode: DT11 0RD, Grid Reference: ST812093, What Three Words: district.political.tasks).
Refreshments – None on route but you can divert off to The Cricketers in Shroton (Iwerne Courtney) or The Old Ox Inn in Shillingstone.
The route – Unfortunately it is not possible to cycle the whole Wessex Ridgeway as it is based mainly on footpaths. Instead Dorset County Council advises you to take a slightly different route, which is what I follow.
The first thing I recommend is to do this during the summer months, when it’s drier. In the winter in can get very muddy and I spent almost half the ride pushing the bike through thick mud. Uphill!
The ride starts brilliantly. Heading out of Ashmore, the highest village in Dorset, follow the road to the west to quickly turn left, onto a farm track. Ignore any diversions and shortly you enter into the woods. In the spring time, these are famed for their bluebells. The solid path disappears and you have your first interaction with the mud. Stay to the path, following any Wessex Ridgway signs, keeping left, until you come to a T junction. Turn right and follow the path through the woods down the hill. At the bottom turn left keeping the woods on your right. Eventually, the ground becomes more solid again and brings you out into a road at the village of Stubhampton in the Tarrant Valley.

Turn right to start the slow uphill climb. The road cuts through a valley with woodland, slowly getting thicker on your right hand side. Again these woods are also gorgeous bluebell sites. Pass the farm drive on your left and you’re about half way up. At the top of the hill, ignore the footpath at the lay-by and pass the wood on your left. A bridleway sign then guides you into the trees on your left. This particular wood is an easy one to cycle though, it is downhill which helps, but seems to be less churned up than the tracks used so far.
Once out the woods, ignore the Wessex Ridgeway sign that tells you to turn right up the hill. Instead continue straight ahead, remaining in the valley. Follow the track at the bottom of the field with trees on your left. When you enter into deeper woodland, the earthwork remains of Harbins park are on your left.
Harbins park was an old enclosed deer park. Its boundary can still be made out as earthworks that rise from up the ground. When you reach a road the track continues straight over which suggests, with the presence of the park too, that this crossroads was once a much busier junction.
Instead of staying on the track, turn right on the road, climbing another hill. It is a quiet lane but narrow and steep in places. Once at the top you meet the top Blandford to Shaftesbury road. Cross over onto Smugglers Lane. Again, this track was once much more popular. Its name alone suggests that is has been heavily utilised by those that require fast and easy routes across the lamdscape. Behind you lies Cranborne Chase, an area that was heavily used for hunting. The proximity of the Chase was taken full advantage of by the Beckford family from Stepleton House in Iwerne Courtney, which sits in the next valley. It was in the late 18th century when they were renowned for their celebrated dog kennels used for fox hunting; even writing books on the subject. Smugglers Lane provided the direct route from their house to the hunting ground.

Further back into history, this route could have been used by the Romans to link Hod Hill to Badbury Rings. Also located in the east, only the opposite side of the Tarrant Valley, is a small earthwork know as Caesar’s Camp, a Roman villa has also been discovered.
Continue straight ahead, over the road to follow Smugglers Lane. Again it can be a muddy path but, once you cross over another track and start to descend downhill, the ground becomes firm. This helps you pick up speed despite the mud. Stepleton house passes on your right and once at the bottom of the hill you join the A350. Be careful as you couldn’t have joined this road on a trickier bend. Follow it straight ahead and around to the right, it has a slight incline too, so if your legs are getting tired, take it steady.

Turn left at the next junction, signposted to Hanford School. If you are up for it you can then take the bridleway on your right to climb Hambledon Hill, if not remain on this road until you get to Hanford School. To get to Hambledon, remain on the track with the trees on your right. Take the next track on your left climbing up the hill. Continue to follow it until you meet a junction with other footpaths along with an linear earthwork and a trig point. The views have opened up all around you and on a clear day you can see for miles. You can also look back at the path you’ve already travelled to arrive here. Turn left leaving Hambledon behind and keep tightly right to descend the hill. When you meet the road turn left again to get to Hanford school.

Cycle straight down to the school drive, forking slightly right, passing some houses on your right too. Turn right though a gate where the Ridgeway is signposted. Go through the next gate and into the farmyard. Head to the end and turn right and then left to enter the field. Be aware as in this area there are plenty of warnings for bulls. Keep the field boundary on your right go all the way down to the next boundary, through another gate and come out onto a small path with the river Stour below you. Turn left and following, at first, the river down stream, hidden amongst the trees. Go through a gate at the end, turn right and through a big gate and the footbridge across the Stour can be seen ahead. Make your way to it but again, be mindful of any livestock.

Cross over the bridge and straight over the next field, through a gate and onto another enjoyable hard surface. Ignore the turning to your right and continue straight on. Look out for the old Somerset and Dorset railway, now the North Dorset Trailway, approaching on your left as you then go under its original bridge. Shortly after the bridge you come out onto the A357. Cross straight over and enter the field. Head across aiming to the left side of the houses (the OS map, slightly in error here). Come out onto another small road and turn right. Turn left at the next junction, signposted Wessex Ridgeway. Here your final climb starts, and its the longest and steepest of all.

Follow the road and ignore the first right hand path into the woods and take the next one, clearly signposted. The climb starts to get a bit steeper, but thankfully the ground, although muddy, isn’t overly used by horses so it’s not as mushed up as previous tracks. Its is a long climb and you’ll be relieved to see the sign at the top. Turn right and follow the track along. As you meet other paths, the ridgeway is waymarked well so you won’t get lost. On your right is Okeford bike park, a hidden little attraction that isn’t advertised much, other than on the local signs and is slightly worse for wear. Once again you meet another track and your route becomes firmer. Follow the track to the end where you meet the road. Turn right, up a small climb and you arrive at Okeford hill car park on your left.

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