This four-and-a-half mile route is one of our favourite walks, a family tradition on Boxing Day but also glorious in summer. It’s moderate in difficulty (some steep climbs and descents, including some steps), but you’ll want to allow around two-and-a-half hours.
Start at the Coombe Hill National Trust car park, go through the gate and take the footpath to your left. This will take you downhill through the woods. Take care, as the path is quite steep in parts. At the bottom, you emerge on to a lane. Cross the road at the junction with Missenden Road, cross, turn right, and after a short distance, take the footpath on the left, which crosses a field. Ahead you can see the distinctively shaped grassy mound of Beacon Hill.
At the end of the field, emerge on to a lane and turn right. At the end of the lane you can cross the road to make a detour to the Church of St Peter and St Paul, Ellesborough, where prime ministers sometimes worship. Turn left along the road and take the footpath on your left through a grazing meadow. Look back for views of Ellesborough village and church. After passing through a gate, continue uphill and slightly to the right around the side of Beacon Hill. The earthwork to your right is the remains of a medieval motte and bailey castle, known as Cymbeline’s Castle.
Pass through a gate and on to a fenced path through a wooded area – the largest native box woodland in the country. Ignoring the private driveway, take the path to the left (the path to the right will take you towards Pulpit Hill). After a while you will see Chequers to your left.
Take the gate on the left and follow the path through the Chequers Estate, before emerging on a bend in the road. Cross the road with care. To your right is Buckmoorend Farm Shop, where you can enjoy refreshments – even canine companions can enjoy a few homemade dog treats. Follow the path up through the wood, and when you reach a junction, turn left, following the path through the wood.
You will emerge on the road, where you should turn right and after a short while take the footpath on the left. This will cross the path you originally took down the hill. At this point you can turn right to return to the car park, but if you continue straight, you will reach the Coombe Hill Monument, with wide-ranging views across the Vale of Aylesbury.