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Road cycling routes

South West England

Winters Lane – Upwey Wishing Well loop from Dorchester West

Road cycling routes

South West England

Winters Lane – Upwey Wishing Well loop from Dorchester West

Moderate

4.4

(5)

135

riders

Winters Lane – Upwey Wishing Well loop from Dorchester West

02:12

40.2km

460m

Road cycling

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride. The starting point of the route is accessible with public transport.

Last updated: August 21, 2026

Tips

Temporary access restrictions

Includes segments with temporary access restrictions.

After 40.0 km for 191 m

Customers only

Waypoints

A

Start point

Train Station

1

424 m

Market Café in Dorchester

Highlight • Cafe

2

5.25 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

12.5 km

Hyde Coppice

Forest

20.3 km

Chester's Coppice

Forest

5

26.2 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

6

32.3 km

Upwey Wishing Well

Highlight • Historical Site

This sweet wishing well is actually the source of the River Wey, which flows south and enters the Channel at Weymouth. Unlike the sources of many rivers which are found …

Tip by

7

33.9 km

View of Maiden Castle and the Dorset Countryside

Highlight • Natural Monument

at the top of Goulds Hill you'll have one of the best views of possibly the most impressive Iron Age Fortresses on the planet

Tip by

B

40.2 km

End point

Train Station

Way Types & Surfaces

Way Types

33.1 km

5.39 km

1.19 km

170 m

164 m

148 m

< 100 m

Surfaces

21.6 km

18.2 km

239 m

133 m

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Elevation

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

Highest point (140 m)

Lowest point (10 m)

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Weather

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Saturday 10 October

16°C

9°C

-- %

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