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South West England

Weymouth And Portland

View of Maiden Castle – Winters Lane loop from Upwey

South West England

Weymouth And Portland

View of Maiden Castle – Winters Lane loop from Upwey

Hard

2

riders

View of Maiden Castle – Winters Lane loop from Upwey

02:34

38.2km

530m

Gravel riding

Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels. The starting point of the route is accessible with public transport.

Last updated: April 3, 2026

Tips

Includes a very steep uphill segment

You may need to push your bike.

After 3.05 km for 123 m

Waypoints

A

Start point

Train Station

Get Directions

1

3.41 km

Dirt Path in Dorset National Landscape

Highlight • Forest

4.86 km

Down Wood

Forest

6.58 km

South Plantation

Forest

4

13.5 km

Chalky Trail in Dorset National Landscape

Highlight • Trail

Keep those eyes peeled, may see some baby calves in the approaching farm..

Tip by

5

14.2 km

Gravel path from Maiden Castle to Martinstown

Highlight • Trail

This is now laid with tarmac and is a very comfortable ride now. More like a large footpath now.

Tip by

6

14.5 km

View of Maiden Castle

Highlight • Cycleway

This is now very easy going with a couple of gates. Surface is smooth path now.

Tip by

7

20.6 km

View of Hardy Monument and the Coast

Highlight • Viewpoint

The long climb to the monument from Martinstown is rewarded with 360 views of Black Down and the coast.

Tip by

8

23.8 km

Valley of Stones

Highlight • Natural Monument

This National Nature Reserve has an unusual train of sarsen stones – boulders strewn across the valley, tumbled down from the ridge during the last Ice Age

Tip by

9

25.9 km

Winters Lane

Highlight (Segment) • Trail

A great quiet lane for faster riding leaving Portesham heading east, with some twisty bits and a lovely view down to the sea.

Tip by

10

34.7 km

View of Weymouth and Dorchester

Highlight • Cycleway

Be careful as it is unpaved. Passable on a road bike, and offers a good alternative to busy roads.

Tip by

B

38.2 km

End point

Train Station

Way Types & Surfaces

Way Types

23.0 km

6.58 km

4.50 km

2.89 km

1.14 km

127 m

Surfaces

15.7 km

11.6 km

7.37 km

1.80 km

1.75 km

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Elevation

Elevation

Nothing selected – click and drag below to see the stats for a specific part of the route.

Highest point (200 m)

Lowest point (20 m)

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Weather

Powered by Foreca

Friday 26 June

25°C

16°C

11 %

Additional weather tips

Max wind speed: 15.0 km/h

to get more detailed weather forecasts along your route

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