HILLY HIKE 20km Hastings to Rye - Saxon trails and Medieval Coastal Towns

📏 Key Info:
• Distance: 12 miles (20km)
• Grading: Intermediate but with tough hills
• Ascent: 468m
• Hiking time: 5 to 6 hours
• Cost: £32 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, 1 hour after the lunch stop, and at the end pub
📍 Meeting Point
• Location: Victoria station. Meet between WHSmith (no 34) and Nero Express (no 29) - MAP & photo
• Time: Meet 8:20am, leave 8:40am for the 8:54am train
• Return: 8:36pm arrival back in London (you’re committed until then)
🌟 Highlights
• Explore Hastings, home to Europe’s largest beach-launched fishing fleet and historic net huts
• Follow the scenic Saxon Shore Way along one of the South East’s most dramatic coastlines
• Enjoy panoramic cliff-top views, with France visible across the Channel on a clear day
• Visit Winchelsea, a medieval port town once on the coast before the sea receded
• Discover the cliffs’ Site of Special Scientific Interest, where dinosaur fossils and crocodile remains have been found
• End in Rye — one of England’s most enchanting medieval towns, with cobbled streets and timbered houses
🥾 Hike Description
Our hike begins in Hastings, best known as the site of the famous 1066 battle where William the Conqueror defeated King Harold. Today, Hastings is a lively coastal town and home to Europe’s largest beach-launched fishing fleet, a sight made even more distinctive by the tall black wooden fishing net huts that line the seafront.
From here we join the Saxon Shore Way, a historic coastal route named after the Roman forts that once guarded England’s shores. The path climbs onto dramatic sandstone cliffs that have been designated a Site of Special Scientific Interest for both their geological and biological importance. As we traverse the cliff tops, the sea views are spectacular, with France sometimes visible across the Channel. Along the way, we’ll learn how the cliffs have revealed dinosaur fossils and even crocodile bones from the Early Cretaceous Period, over 140 million years ago.
The route then leads us inland to Winchelsea, a medieval port town founded in the 13th century. Once a thriving harbour, the sea has since retreated, leaving Winchelsea perched inland but still rich in history, with ancient walls, medieval cellars and atmospheric streets to explore.
We finish in the enchanting town of Rye, one of England’s most beautifully preserved medieval gems. With its cobbled streets, half-timbered houses and centuries-old inns, Rye provides a perfect finale to our hike. Here you’ll have some free time to explore before we return by train.
TOUGHNESS, PACE - this hike has some big and tough hills, also it's done at a good pace as timings are tight, please only sign up if you are happy with this.
🧭 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)
📲 Explore More & Stay Connected
Day hikes list 👣
Calendar - All trips 📖
Instagram 📸
Facebook page & Photos group
📄 Terms and Conditions
By signing up or attending you agree to our Terms and Conditions
© Outdooraholics Hiking UK Ltd 2026 E & OE

Know what’s Happening Next — before everyone else does.

Get App

Host or Publisher Outdooraholics