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Hiking trails & Routes

South East England

Worsley Obelisk – Freemantle Gate loop from Ventnor

Hiking trails & Routes

South East England

Worsley Obelisk – Freemantle Gate loop from Ventnor

Hard

4.0

(2)

4

hikers

Worsley Obelisk – Freemantle Gate loop from Ventnor

05:18

18.1km

490m

Hiking

Hard hike. Very good fitness required. Easily-accessible paths. Suitable for all skill levels. The starting point of the route is accessible with public transport.

Last updated: April 18, 2026

Tips

Your route passes through protected areas

Please check local regulations for:

Isle of Wight National Landscape

Waypoints

A

Start point

Bus stop

Get Directions

1

2.95 km

View from Stenbury Down

Highlight • Viewpoint

2

4.84 km

Worsley Obelisk

Highlight • Monument

Great picnic spot

Tip by

3

5.56 km

Freemantle Gate

Highlight • Monument

Head down for a short detour to the English Heritage site at Appuldurcombe House

Tip by

4

9.60 km

View of Shanklin and Culver Cliff

Highlight • Viewpoint

5

11.3 km

View of Sandown Bay from Haddon's Pits

Highlight • Natural

Haddon's Pits is a nature reserve in the Isle of Wight offering sensational coastal views and a variety of habitats including ponds, wetlands, and grasslands.

Tip by

13.3 km

The Landslip

Forest

7

15.0 km

Stokey's Solar System Walk

Highlight (Segment) • Monument

This walk along the sea wall between Bonchurch and Ventnor features a scale model of the solar system. You can see just how far away the outer planets are from …

Tip by

8

16.0 km

Wheelers Bay Beach

Highlight • Beach

Attention: Since November 2022, part of the Eastern Cliff Esplanade has been closed due to damage or repair work!

Translated by Google •

Tip by

9

16.7 km

Ventnor Breakwater

Highlight • Structure

A pleasant place to sit off the coast of Ventnor, with panoramic views of the sea, the seafront and up to the town.

Tip by

B

18.1 km

End point

Bus stop

Way Types & Surfaces

Way Types

7.52 km

4.68 km

1.82 km

1.64 km

1.26 km

692 m

510 m

Surfaces

6.91 km

3.19 km

2.76 km

2.61 km

2.03 km

628 m

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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 (220 m)

Lowest point (0 m)

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Weather

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Thursday 21 May

21°C

14°C

-- %

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Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.

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