Chiltern Hills, Coombe Hill monument, Chequers (PMs country retreat), 14km

This circular hike starts from Wendover, a market town at the foot of the Chiltern Hills Area of Outstanding Natural Beauty (AONB) in Buckinghamshire.

As we walk across the beautiful countryside, we reach the summit of Coombe Hill at 260m, which provides panoramic views of Aylesbury Vale. On a clear day it seems you can see as far as Thame, Oxford, and Didcot. You will see a section of the Chiltern Escarpment from Wendover Woods to Aston Hill and Ivinghoe Beacon, a prominent viewpoint at 233m.

The Coombe Hill Monument (the Boer War Memorial) at the summit of Coombe Hill is an iconic landmark and one of the largest examples of a war memorial. It was built in 1904 to commemorate those who died during the war in South Africa (1899-1902).

The hike continues through the surrounding hills and forest to Chequers, the Prime Minister’s country retreat. There is a farm shop here where we can rest for a bit if required (and if it's open). We then continue onwards through the forest to reach Wendover station and complete the loop.

Cost: £4 organiser fee payable on RSVP

Start time: 10:00am

Start location: Wendover station, Station Approach, Buckinghamshire HP22 6BN (my mobile: 07951673142)

End location: Wendover station

Length: 14km

Ascent: 390m

Time: approx 6 hrs. It’s not possible to guarantee what time we'll finish as it depends on the weather, pace of the group and our breaks along the way.

Pace & Difficulty: a reasonable moderate pace; we will not be zooming along in a mad rush. The aim is to enjoy the outdoors and have a fun, friendly day. You need to be reasonably fit; we will cross some hills and there is a moderate level of ascent.

Transport (train): The 8:34am train from London Marylebone reaches Wendover station at 9:58am (with one change at Amersham). The journey takes 1hr 24min. Check the trains before travel. There are trains every 1hr for the return journey later in the day from Wendover to London Marylebone.
As of 22 February 2026, an Off Peak Day Return costs £10.60.
Please do your own research.
You can reduce the train cost by one third with a Network Railcard, where applicable.
You could also coordinate with other participants and buy a group saver ticket.

Transport (car): If you're driving, there is free parking on the side streets close to the station (not the main road). Check the signs.

Transport (car share): I'll be driving from Ealing, West London and have space for 3 passengers. Contact me directly if you'd like to car share.

What to bring:
Check the weather and bring appropriate gear. A comfortable backpack, waterproof jacket, sufficient food, snacks, and water along with suitable socks and footwear (waterproof hiking boots) are some essentials. Walkways and trails can be steep, muddy, and slippery and boots with ankle support will be useful, as well as hiking poles. Gaitors are handy when its muddy and wet. Carrying waterproof socks in your backpack is a good idea in case your boots get wet from the inside. Don't wear inappropriate clothing such as jeans and sneakers. Remember to carry any medication you may require. If it’s sunny, don’t forget a hat, sunglasses and sunscreen!

IMPORTANT DISCLAIMER / TERMS AND CONDITIONS:
By participating, you confirm you have read, understood and accepted the below, including the full Terms and Conditions
I am NOT a qualified hike leader or first aider.
Hiking, walking, and hill walking carry the risk of personal injury and death. Participants must be aware of, and accept, the risks. Participants are responsible for their own safety and actions and agree not to hold me responsible or liable for any injury (or death), damage or losses incurred either directly or indirectly from their participation in group events. This group is for people 18 years old and over.