Coombe Hill and Chequers Court Circular Walk

The Coombe Hill and Chequers Court Circular Walk in the Chilterns is a long, scenic hike through the countryside with some undulations. Do note that rainy weather creates a muddy, slippery trail, so be mindful of this when you’re descending! You will also navigate some kissing gates on this route. Lastly, Coombe Hill Car Park can get super busy on weekends—aim to arrive early.
This walk immerses you in nature, granting stunning views of Aylesbury Vale while also carrying you by remnants of history. You’ll catch a glimpse of the prime minister’s estate at Chequers! Expect to walk through hushed, secluded wooded areas as well.

The walk starts from Coombe Hill Car Park. From here, you’ll walk through the gate for National Trust property, and once through, you’ll follow the path swerving to the left—going away from the path beside the fence for the picnic area. Continue on a relatively straight path through the grassland towards the opening of trees. Go through the gap and take a slight right to walk across more grassland, heading towards the Boer War Memorial.

Revel in the views of Aylesbury Vale here before following a path to the right of a tree and two markers. It’ll feel like you’re retracing your steps, but you aren’t! 164ft from the Memorial, you’ll see a bench. Take a right for a diagonal descent. Notice Chequers emerging into view! You may encounter some anthills at the bottom of the path in the grassland to your left.

When you see the boundary fence and wooded area, look for a trail on your right. Take this path and go on a steep descent through shaded woodland. This path can be slippery after rain! When you reach the bottom, take a left onto the bridleway. Continue along this path, walking by Ellesborough Golf Course. Upon arrival at the corner of the National Trust property, you’ll take a right and navigate a gate before going downhill. Cross the path leading towards the road and take a right to go on the footpath. 328ft later, take a left onto another footpath with a sign, which will take you across a field. Continue until you get to another intersection.

Take a right and go towards Ellesborough. Some of you may want to visit the church here! You’ll have to cross the road, so be careful when you do. From here, you’ll turn left, following another footpath towards a kissing gate, which you’ll pass through to reach a field. Continue along the same path, going diagonal, where you’ll navigate another kissing gate to reach another field. Get ready for an ascent up Beacon Hill! To begin the climb, follow the path to the left of the gate.

After catching your breath, you’ll head down the hill by turning right to go along a narrow path just before the trees at the top. This path will merge with a public footpath. Take a left and walk towards the trees. When you reach the gate, go through it, head up a set of steps, and go through another gate. Continue along the path, crossing a field. When you get to a wire fence, ignore it, and go through the gate at the edge of the field. This next track will take you into woodland!

Soon after that, you’ll cross a track to reach another gate. This is where the walk looks up and around Pulpit Hill. Take a right at the gate to walk under a canopy of trees. You’ll see a sign for Outer Aylesbury Ring. After the trees, walk towards a wooden gate and go through it. Bear left up a tiny slope! At the top, take a left, and views of Great Kimble Common, Happy Valley, and the Aylesbury Vale will take over the scenery. The path will dip below the ridge and take you past a wooden gate towards another kissing gate.

Head through the gate and take onto the Ridgeway path. When the path reaches grassland, stay left on the well-maintained path. Continue along this path. 49ft after you cross a different path, and straight across from a marker for the Ridgeway, turn right onto a grassy trail. The path then takes you up to Chequers Knap.

Take the right path that goes down Chequers Knap back onto the Ridgeway, meeting up with a gate. Go through it and take a right. 98ft later, take a left and follow some steps down and go through another kissing gate. Continue along the undulating Ridgeway. You’ll then pass a bench, and 98ft later, head off the Ridgeway to go along a path to your left until you meet up with the bridleway on your right.

Go until just after a metal gate, where you’ll turn left, heading uphill. Follow the sign indicating Pulpit Hill Fort – 1640ft. The signs will have you taking a sharp left and a sharp right. Soon, you’ll encounter remnants of an ancient hill fort. Take a left to enter the fort. At the T-junction, take a right, going downhill. Go across another path and through a kissing gate. When you reach another web of crossing paths, go right, through a metal gate, and back onto the Ridgeway. After 1804ft, take a left, going through another gate. Continue following the signs for the Ridgeway. Eventually, you’ll reach a road that requires crossing. Be mindful as it’s on a blind corner! And sometimes it’s hard to hear the traffic when it’s windy. When you’re across, look for the sign for the Ridgeway, which takes you through a wooded area. Look for waymarks with an acorn symbol!

Soon, you’ll reach the road. Ascend it for 492ft before taking a left at the Ridgeway sign. Continue along, passing through a kissing gate. After, take a right to follow the path that will take you back to the car park.

Trail Highlights

Boer War Memorial

This Memorial was originally constructed in 1904 to commemorate the Buckinghamshire men who died in the Boer War. It was then struck by lightning but restored by 1939. During World War II, the Boer War Memorial caused problems as it was an easy striking point for enemies.

Pulpit Hill

Pulpit Hill is an Iron Age hill fort, which was more so used to store agricultural produce and to keep animals in!

Other amazing walks in Chiltern Hills

Check out our guides to Wendover Loop, Wendover Woods, Dunstable Downs, Hurley Loop or The Rose and Crown Ivinghoe Beacon Walk. Or see all of our Chiltern Hills walks on 10Adventures.