To help you find the best hikes and walks around Winterbourne Steepleton, we’ve reviewed our full collection of trails and routes in the region. Browse all of the details of each route below — and explore more of the nature around Winterbourne Steepleton.

Last updated: November 7, 2025

4.4

(9)

hikers

1. Portland views from Hardy's Monument — National Trust coastal walks in West Dorset

7.42km

02:11

210m

Intermediate hike. Good fitness required. Mostly accessible paths. Sure-footedness required.

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Intermediate

5.0

(3)

hikers

2. Hardy Monument Trail — National Trust North and West Dorset

5.97km

02:02

130m

Intermediate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.

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Intermediate

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4.7

(10)

hikers

3. Hardy Monument – Smitten Corner Trail Junction loop from Portesham

3.47km

00:59

80m

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

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Easy

4.6

(7)

hikers

4. Hardy Monument – Smitten Corner Trail Junction loop from Winterbourne Steepleton

4.95km

01:24

110m

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

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Easy

4.7

(9)

hikers

5. Hardy Monument – Maiden Castle Hillfort loop from Portesham

15.2km

04:14

290m

Intermediate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.

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Intermediate

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Other adventures around Winterbourne Steepleton

20 fantastic trails in North & West Dorset — National Trust

Hiking Collection by

National Trust North and West Dorset

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Cycling around Winterbourne Steepleton

Road Cycling Routes around Winterbourne Steepleton

Easy hikes around Winterbourne Steepleton

Gravel biking around Winterbourne Steepleton

Most popular attractions around Winterbourne Steepleton

Places to see

Natural Monuments

Lakes

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The best walks and hikes around Winterbourne Steepleton

1. Portland views from Hardy's Monument — National Trust coastal walks in West Dorset

2. Hardy Monument Trail — National Trust North and West Dorset

3. Hardy Monument – Smitten Corner Trail Junction loop from Portesham

4. Hardy Monument – Smitten Corner Trail Junction loop from Winterbourne Steepleton

5. Hardy Monument – Maiden Castle Hillfort loop from Portesham

Other adventures around Winterbourne Steepleton

Most popular routes around Winterbourne Steepleton

Most popular attractions around Winterbourne Steepleton

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