To help you find the best hikes and walks around Winterborne Monkton, 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 Winterborne Monkton.

Last updated: November 11, 2025

4.5

(2)

hikers

1. Maiden Castle & Romano Brisith Temple loop — Dorset

2.61km

00:44

60m

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

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Easy

4.8

(6)

hikers

2. Maiden Castle Hillfort loop from Poundbury

8.58km

02:18

100m

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

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Moderate

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4.6

(8)

hikers

3. Maiden Castle Hillfort – Hardy Monument loop from Poundbury

15.9km

04:27

320m

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

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Moderate

3.0

(1)

hikers

4. Hardy Monument – Maiden Castle Hillfort loop from Poundbury

24.5km

06:50

460m

Hard hike. Very good fitness required. Easily-accessible paths. Suitable for all skill levels.

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Hard

3.7

(3)

hikers

5. Bronze Age Burial Mounds – Upwey Wishing Well loop from Upwey

8.56km

02:24

170m

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

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Moderate

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Most popular attractions around Winterborne Monkton

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The best walks and hikes around Winterborne Monkton

1. Maiden Castle & Romano Brisith Temple loop — Dorset

2. Maiden Castle Hillfort loop from Poundbury

3. Maiden Castle Hillfort – Hardy Monument loop from Poundbury

4. Hardy Monument – Maiden Castle Hillfort loop from Poundbury

5. Bronze Age Burial Mounds – Upwey Wishing Well loop from Upwey

Most popular routes around Winterborne Monkton

Most popular attractions around Winterborne Monkton

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