Old Town, Rye – Winchelsea Beach loop from Rye

Bike touring routes & trails

Old Town, Rye – Winchelsea Beach loop from Rye

Moderate

4.7

(3)

riders

Old Town, Rye – Winchelsea Beach loop from Rye

02:27

39.1km

340m

Cycling

Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels. The starting point of the route is accessible with public transport.

Last updated: September 10, 2026

Tips

Includes a segment in which cycling is not permitted

After 16.3 km for 52 m

Waypoints

Start point

Train Station

Get Directions

498 m

Old Town, Rye

Highlight • Historical Site

great old town

Translated by Google •

Tip by

6.44 km

Winchelsea Beach is one of the few remaining relatively undeveloped parts of the south coast. Slightly inland, between the coast road and the sea, is this odd shingle landscape known as "The Ridges" - shingle and rugged land with a jumble of 1930s bungalows dotted along the dirt roads. The whole area is highly appreciated by those who love fresh air - flocks of birds and open and empty spaces. The beach is calm and never crowded with pebbles at high tide and flat sand at low tide.
tourist.org.uk/east-sussex/winchelsea-beach

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Tip by

10.2 km

Pett Level WW2 Bunker

Highlight • Historical Site

Pett Level WW2 bunker

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13.7 km

Battery Hill Viewpoint

Highlight • Viewpoint

At the turn of the century, a local gun battery from Battery Hill is said to have regularly practiced firing. Fire was aimed at the sea; this was probably the origin of the name "Battery Hill". Centuries before William the Conqueror built a manor house in Fairlight, which he gifted to the French Countess of the EU, her husband was Hastings Castle's first agent.

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19.3 km

Hastings Net Shops

Highlight • Historical Site

Since the 17th century the fishers used to dry and repair their nets in these narrow huts.

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19.4 km

East Hill Cliff Railway

Highlight • Historical Site

You can take the East Hill Cliff Railway up the cliff to the Hastings Country Park. The lift takes you 267 feet (81 meters) up the hillside, where you can enjoy stunning views over the sea and Hastings. With a 78% gradient, it's the steepest funicular railway in the UK.

The railway, which opened in 1902, has been ferrying holidaymakers for over a century and has become a source of local pride in Hastings.

The train runs from 11am - 4pm daily during summer and return tickets for adults cost £3.50. In winter, it only runs on weekends.

For more information, visit: visit1066country.com/things-to-do/cliff-railways-east-hill-p1424931

Tip by

20.1 km

Hastings Old Town High Street

Highlight (Segment) • Historical Site

Lovely old high street with a great mix of independent shops, some really quirky, a variety of restaurants and cafes.

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25.3 km

Three Acre Wood

Forest

29.5 km

Pett Level Road

Highlight (Segment) • Cycleway

Pett Level Road is a road that runs along the coast of East Sussex, connecting the villages of Pett Level and Winchelsea Beach. It is about 2.5 miles long and has various properties and attractions along it

Tip by

39.1 km

End point

Train Station

Way Types & Surfaces

Way Types