​

Challenging Chillerton Down Walk, Isle of Wight

Loop Walk · Isle of Wight

400

XP

about 3 h 22 min walking

Strenuous
14.65 km
Loop
03:30-04:00
Graded from its length and climb.

A challenging circular walk that takes you off the beaten track, through woods & valleys, & across the Chillerton Downs with sea views. The route includes undefined paths, gates, bridges & a stile & can be slippery. Dogs welcome on leads around livestock

0 km2 km4 km6 km8 km10 km12 km14 km

366 m

183 m

0 m

Scroll along the route · tap the chart to find a point on the map

Heights: Copernicus DEM GLO-30 © DLR e.V. 2010–2014 and © Airbus Defence and Space GmbH 2014–2018, provided under COPERNICUS by the European Union and ESA.

Navigate to the start
Google MapsApple MapsWaze
Weather at the start
More trail infoRoute from OpenStreetMap contributors

Steep walk

Some very steep ground — marked on the map.

Climb

269 m

Drop

263 m

Highest

161 m

Lowest

16 m

Which way round

Clockwise: Climbs 18% for 200 m early on, comes down 17% for 220 m early on.

Anticlockwise: Easy first 9.4 km, climbs 17% for 220 m near the end, comes down 18% for 200 m near the end.

Better clockwise: you climb the steeper side (0.4 km at 10%+, 0.4 km of it 15%+) and come down 0.2 km of steep ground. Steep descents are where people slip, and they're harder on knees late in a walk.

Main descent: km 2.1–3.2, from 139 m to 58 m.

How the 14.6 km splits

Flat

4.4 km

Climbing

4.3 km

Very steep climbing (15%+)

0.4 km

Descending

5.3 km

Very steep descending (15%+)

0.2 km

Link it with other walks

Shepherds Trail

Shares 3.5 km of path · meets at km 2.9, 11.2, 13.9

12.43 km

Chillerton Down Circular Walk, Isle of Wight

Starts here too · Shares 3.3 km of path · meets at km 0.0, 14.4

7 km

Worsley Trail

Shares 1.3 km of path · meets at km 0.0, 13.9

21.28 km

The Stenbury Trail

Shares 0.3 km of path · meets at km 6.7, 6.8

15.02 km

Chalk Ridge Extreme

Shares 0.2 km of path · meets at km 6.4

85.63 km

About AVANDRA

Your ultimate trip planner for adventurous getaways.

Quick Links

Trips

Connect With Us

© 2026 AVANDRA. All rights reserved.