TOUGH HIKE 27km Winston Churchill’s glorious Kent & his mansion - Chartwell

📏 Key Info:
• Distance: 17 miles (27km)
• Grading: Challenging
• Ascent: 650m
• Hiking time: 7 to 7.5 hours
• Cost: £30 plus Eventbrite fee they charge including the guided hike and return train travel, click “Get Tickets” to join.
• Payments are refundable upto 7 days in advance, after that they are non refundable and non transferrable.
• Toilet Breaks: On the train, at the lunch stop, and at the end pub
📍 Meeting Point
• Location: Victoria station. Meet between WHSmith (no 34) and Nero Express (no 29) - MAP
• Time: Meet 8:20am, leave 8:35am for the 8:50am train
• Return: 6:32pm arrival back in London (you’re committed until then)
🌟 Highlights
• Begin in the charming town of Oxted, where the Greenwich Meridian passes through
• Pass the historic Tenchleys Manor (1599) and the Edwardian Emmetts Garden estate
• Visit Chartwell, the country home of Sir Winston Churchill
• Explore Crockham Hill, the village where Octavia Hill lived and is buried
• Climb Toys Hill (235m), the place that inspired the founding of the National Trust
• Hike through the countryside and rural beauty of Limpsfield Common and Westerham
🥾 Hike Description
Our hike begins in the picturesque town of Oxted, with its timber-framed buildings and a unique claim to fame — the Greenwich Meridian passes directly through the local school. From here, we follow the Greensand Way across open meadows and into Limpsfield Common, before reaching Tenchleys Manor, a historic house built in 1599.
The trail continues to the village of Crockham Hill, once home to Octavia Hill, the pioneering social reformer and co-founder of the National Trust. She chose to be buried here, and much of the land around the village was secured for the Trust thanks to her efforts. From here we head to Chartwell, the family home of Winston Churchill, where the wartime leader spent much of his adult life.
Climbing higher onto the Greensand Ridge, we reach Toys Hill (235m), a hamlet perched on the steep scarp slope that offers sweeping views across the Weald. It was here that Octavia Hill’s vision for the National Trust was first inspired. After pausing to take in the panorama, we continue on to Emmetts Garden, an Edwardian estate on Ide Hill with beautifully landscaped grounds.
Our hike concludes with a scenic walk through the countryside towards the charming village of Westerham, before looping back to Oxted. It’s a day of history, countryside, and inspiration, tracing the footsteps of both Churchill and Octavia Hill in the heart of Kent’s rolling landscapes.
🧭 Guide:
• Leader: GRAHAM
• Contact (hike day only): 07796 098487
🍽️ Food:
• Bring a packed lunch
• Pub visit after the hike (drinks optional)
🎒What to Bring
• Hiking boots/shoes
• Water (2 litres minimum)
• Packed lunch
• Waterproofs (jacket and trousers)
• Hat and gloves if cold
• Train tickets are arranged – just meet us at the meeting point
⚠️ Safety
Your guide is a trained hike leader and Outdoor Activity First Aider
❓ Want to Know More?
• New to Our Trips? (perfect for first-timers, answers “what to expect”)
• About Us (who Outdooraholics are, credibility, history)
• FAQs (covers common queries)
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