Running around Winterborne Monkton is one of the best ways to explore more of this region. To help you discover the most beautiful places to run, we’ve reviewed our full …

Last updated: September 25, 2025

4.0

(2)

116

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1. The Great Field parkrun loop from Dorchester

8.90km

00:56

60m

Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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2. The Great Field parkrun – View from Poundbury Hill loop from Poundbury

10.1km

01:05

80m

Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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3. Tumulus – Tumulus loop from Poundbury

9.82km

01:09

180m

Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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4. Running loop from Poundbury

9.32km

01:03

120m

Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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5. Jubilee Wood – Conquer Barrow loop from Upwey

13.9km

01:27

90m

Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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Most popular attractions around Winterborne Monkton

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The best running trails around Winterborne Monkton

1. The Great Field parkrun loop from Dorchester

2. The Great Field parkrun – View from Poundbury Hill loop from Poundbury

3. Tumulus – Tumulus loop from Poundbury

4. Running loop from Poundbury

5. Jubilee Wood – Conquer Barrow loop from Upwey

Most popular routes around Winterborne Monkton

Most popular attractions around Winterborne Monkton

Get inspired with the komoot mobile app

Explore more

Get ready to conquer new peaks

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