Exploring Upper Winchendon on foot is a delightful way to connect with nature. To help you make the most of your adventures, we’ve compiled the top easy hikes and walks …

Last updated: September 27, 2025

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1. Waddesdon Manor Collections – Waddesdon Manor loop from Waddesdon

3.95km

01:05

60m

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

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4.3

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2. Grassy Field Path – River Crossing loop from Cuddington

3.20km

00:51

30m

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

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Easy

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3. Windmillhill Plantation loop from Waddesdon

5.63km

01:32

90m

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

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4. The Five Arrows loop from Waddesdon

5.13km

01:23

60m

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

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4.0

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5. Waddesdon Hill – Waddesdon Manor Illuminations loop from Waddesdon

5.12km

01:25

90m

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

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Easy hikes and walks around Upper Winchendon

1. Waddesdon Manor Collections – Waddesdon Manor loop from Waddesdon

2. Grassy Field Path – River Crossing loop from Cuddington

3. Windmillhill Plantation loop from Waddesdon

4. The Five Arrows loop from Waddesdon

5. Waddesdon Hill – Waddesdon Manor Illuminations loop from Waddesdon

Most popular routes around Upper Winchendon

Most popular attractions around Upper Winchendon

Get inspired with the komoot mobile app

Explore more

Get ready to conquer new peaks

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