Wendover Woods, Prime Ministers retreat Chequers and Coombe Hill 21km DAY HIKE

Outdooraholics London - Hiking, Adventure Travel - 25 to 40s
Outdooraholics London - Hiking, Adventure Travel - 25 to 40s
Public group

London Marylebone

Melcombe Pl, Marylebone, London NW1 6JJ, UK · London

How to find us

Corina will be at the meeting point detailed in the section "Transport and Meeting Point" below. In case of difficulties locating her you can call her on 07591945281 (texts cannot be replied to)

Location image of event venue


HIKE FULL, but we have now added an additional date, please sign up below:

Come and join us for the delightful Wendover Circular hike which takes us through Whiteleaf and Pulpit Hill and the spectacular Chiltern Hills woodlands. Hike near the famous Chequers estate - a 16th century manor house home to the British Prime Minister. Hike up to Coombe Hill - the highest viewpoint in the Chilterns, which reveals some spectacular views over the Vale of Aylesbury. Our trail takes us through hidden valleys, many varied and ancient woodlands and if open we may also visit a local rural farm shop

Trip Highlights:

• Designated as an Area of Outstanding Natural Beauty in 1965

• Visit charming medieval villages and towns nestled in the Chiltern Hills

• Pass by the Chequers estate - home to the British Prime Minister

• Hike on the Ridgeway - Britain's oldest trail, dating back 5000 years

• Walk up Coombe Hill - the highest point in the Chiltern Hills offering superb panoramic views

• See the Whiteleaf Cross carved into the hillside chalk by monks in the 15th century

Photos - All photos were taken by Outdooraholics on previous trips

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Hike Description

Our hike starts off in the quaint medieval market town of Wendover, nestled at the foot of the Chilterns Hills. It follows an enchanting footpath through magical woodlands, lush green valleys and open fields all the way down to the village of Princes Risborough.

We continue to the adorable Whiteleaf village - distinctive with its ancient cottages and 17th century pub. Hiking further, we pass the curious Whiteleaf Cross carved into the hillside chalk by monks in the 15th century before we enter the Grangelands Nature Reserve below the Iron Age Fort and hike up the Pulpit Hill.

Soon we reach one of the highlights of our hike - the Chequers estate which has been the official country retreat of the British Prime Ministers since 1921. The current house at Chequers dates back to 1565 and has a colourful history including links to the families of Henry VII and Oliver Cromwell. Before returning to Wendover, we hike up to Coombe Hill - the highest viewpoint in the Chilterns offering some breathtaking views.

Transport & Meeting Point

We'll meet at Marylebone station at 8:30am and leave the meeting point at 8:45am for the 8:57am train. Please make sure to arrive on time as the group cannot wait for anyone who is late.

We'll meet in front of the ticket office and wait here. Please click here for a map of our meeting point: https://goo.gl/sLRcjo

Planned arrival time back into London of 6:20pm (we have a group train ticket and you are committed for the day until then).


We'll stop during the hike for a snack lunch so please bring food and drink. We’ll visit a pub after the hike where we can get refreshments.

Distance, Difficulty and Terrain

Distance: 13 miles (21km)
Grading: Intermediate - click here for details:
Ascent: 520m
Hiking time: About 6 hours of actual hiking

Cost and Payment

The trip is £28 per person which includes the guided hike and return train travel from the group departure station listed at the top of this event. To join us please RSVP Yes and you will be automatically redirected to PayPal.

Payments are non-refundable and non-transferable but we have a process to release your space for resale to another member. Please follow the instructions in our FAQ page (https://www.meetup.com/Outdooraholics/pages/6368852/FAQ) and email us with your PayPal “invoice ID” immediately after you change your RSVP to “NO”. If you do not email us at the time of changing your RSVP OR if your space does not sell, you will not be eligible for a refund.

What to Bring

• Suitable hiking clothes & hiking footwear (ideally hiking boots). Waterproof jacket, trousers and footwear are recommended

• Water (at least 1 and ideally 2 litres)

• Packed lunch/picnic

• Money for drinks and refreshments after the hike

• That's it! We will take care of train tickets, logistics on the day etc, so that you can just turn up and have a great day :-)


This hike is led by a trained hike leader (most of our guides are Mountain Leader (https://www.mountain-training.org/walking/skills-and-awards/mountain-leader) trained) and qualified Outdoor Activity First Aider. Outdoor activities involve a risk of personal injury. Please come with hiking footwear and suitable hiking clothes such as warm clothes, waterproof jacket and trousers in case of rain - for more info please click here: http://londonhiking.co.uk/Equipment.pdf

Terms and Conditions

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