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Rye Harbour to Winchelsea Cycle Ride

Distance: 15 km.  Difficulty: Medium.

This delightful Rye Harbour to Winchelsea cycle ride is perfect for families (slightly older children – not tiddlers) or those who aren’t hardcore cyclists. It’s pretty flat (apart from the hill up into Winchelsea which I walked) and there’s only a small amount of roadwork.  For the map readers out there, you need Ordnance Survey Explorer 125 and I recommend starting at Rye Harbour where there is a large car park. If you’re staying in the area or bikeless, there is bike and e-bike hire along Harbour Road between Rye and Rye Harbour.

Rye Harbour, Sussex

The early bird 

Arrive early and have a meander into Rye Harbour Nature Reserve. Well known for its wildlife, there are five birdwatching hides as well as bucket loads of serenity and calm. Then when you’re ready, cycle the 3 km back up the Harbour Road towards Rye. It’s not the prettiest part of the ride but there is a cycle path. When you get to the Brede Sluice, and just before you cross over the river at the foot of Rye town, take the path to your left.

Rye Harbour to Winchelsea cycle ride

This is the Royal Military Canal Path although it doesn’t say as much and it gently weaves its way through the Castle Water Nature Reserve. In April the going was OK but I can imagine it gets very wet in the winter. You cycle through sheep and cattle and right alongside Camber Castle. Then just follow the flat path until you reach a farm. Early morning, this part of your ride is quiet and almost completely uninterrupted, apart from the gates. When you reach the made-up road at the farm, you just stick on that until it joins Sea Road where you head right for Winchelsea or left for the beach. Along the road is the most fantastic little store with fresh orange juice for sale (as well as a selection of game for your tea)!

Rye Harbour to Winchelsea cycle ride

As you approach Winchelsea you join the A259 and go straight on … the Saxon Shore Way is off to your left. The A259 skirts around Winchelsea but if you’ve come all this way, why would you want to do that? Instead, hang a sharp left up the steep hill (there is absolutely no shame in walking this part) and you’ll come to the Strand Gate. If you don’t know Winchelsea already, this is the first clue that you’ve come somewhere remarkably special! This medieval village (officially a town) is hopelessly pretty.

Rye Harbour to Winchelsea cycle ride

Founded in 1288, when Old Winchelsea (which was nearer the shore) was destroyed by the sea, Winchelsea sits high on its hill surrounded by marshland and with views of the sea. It is stacked to the rafters with beautiful houses and architecture and it’s all wrapped up in 13th and 14th century fortifications. It also has an impressive church, museum and even an armoury! You’re about halfway through your Rye to Winchelsea cycle ride here, so pull out your hipflask and sandwich, have a good potter around and when you’re ready, head to Pipewell Gate in the north corner and fly down the steep hill!

Winchelsea, Sussex


Where the main road doubles back at the bottom of the hill, you take Station Road to the smallest station you may ever visit! It was along this stretch that I was lucky enough to see a Hoopoe and I’m immensely grateful to the local birdwatchers for stopping me and pointing it out. These colourful birds are usually found across Africa, Asia, and southern Europe but I gather about 100 or so lose their way each year and end up in this part of the world. Last year one was seen in nearby Icklesham but it’s a rare sight indeed and you’re lucky if you see one!

Rare bird in Sussex

Heading for Rye 

Carry on from here, over the level crossing and at the T junction turn right. You’re on the 1066 Country Walk and it’s a pleasant stretch of path that takes you along the feet of Cadborough Cliff straight into Rye (passed the windmill). Of course, if you haven’t already, you really must stop for a meander around the cobbled streets of Rye before hopping back on your bike and back down Harbour Road to the start point.

Rye, East Sussex

This Rye to Winchelsea cycle ride takes about an hour allowing for some stoppage time for photos and generally absorbing the surroundings but not including time spent in Winchelsea or Rye.

If you like this post about a Rye Harbour to Winchelsea cycle ride, you may also be interested in:

12 Alternative Things To Do In Rye 

Wonderful Winchelsea


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