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United Kingdom
England
South East England
Buckinghamshire
Aylesbury Vale

Upper Winchendon

Easy hikes and walks around Upper Winchendon

4.3

(181)

1,822

hikers

207

hikes

Easy hiking trails around Upper Winchendon are characterized by elevated terrain offering views over the surrounding Buckinghamshire countryside. The landscape primarily consists of arable land and permanent grass, resting on limestone and clay soil. Hikers can expect varied elevations, with some areas reaching 400 feet above ordnance datum. The region provides access to picturesque valleys and historical surroundings, including ancient churches and fragments of 17th-century manor houses.

Best easy hiking trails around Upper Winchendon

  • The most popular easy hiking routeโ€ฆ

Last updated: May 3, 2026

4.5

(4)

26

hikers

#1.

Grassy Field Path โ€“ River Crossing loop from Cuddington

3.28km

00:52

30m

30m

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

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Easy

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

Easy
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5.0

(2)

14

hikers

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

Easy

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

Easy

5.0

(1)

6

hikers

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

Easy
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Tips from the Community

Laura Green
August 17, 2025, River Crossing

nice 11th century church

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Do you need to be a NT member for this?

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Dob
September 7, 2023, The Crown, Cuddington

This is the last pub on the "About Thame!! route for 9 miles until the Three Horseshoes, Towersey.

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This was a great round loop, thereโ€™s a number of stiles to get over and not all are dog friendly, and require a lift, but great walking

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A series of flat, paved, traffic-free roads will lead you around the beautiful, well-kept grounds of Waddesdon Estate.

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Waddesdon Manor is a magnificent 18th-century French Renaissance-style country manor house situated in the town of Waddesdon in Buckinghamshire. As you're running by, look down the avenue and enjoy the sheer beauty and magnitude of this sensational building.

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The powerhouse for the Manor. With the original lift inside

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Sasha Taylor
December 19, 2022, Waddesdon Manor

For the light festival the Parterre was changed into a light spectacular in keeping with the illuminated house. Waddesdon is famous for its Carpet Bedding and every spring and summer we change the design of the beds on the Parterre and on either side of the South Fountain. A French-inspired formal garden, a parterre is made up of a symmetrical pattern of beds set off by mown grass and contained by neat pathways and low clipped hedges. Usually designed to be seen from above, in our case from the raised terrace and the main reception rooms and bedrooms on the south side of the Manor. In the centre sits a magnificent fountain, originally made for an Italian palace in Colorno. The parterre was restored in 1994 to designs by Beth Rothschild. In 2000 Waddesdon won the Europa Nostra award for โ€˜the extraordinary re-creation with modern techniques of a major Victorian gardenโ€™.

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Frequently Asked Questions

How many easy hiking trails are available around Upper Winchendon?

There are over 120 easy hiking trails around Upper Winchendon, offering a wide variety of options for all skill levels. In total, the area features more than 200 hiking routes.

What kind of scenery can I expect on easy hikes in Upper Winchendon?

Easy hikes in Upper Winchendon offer charming views of the Buckinghamshire countryside. You'll experience elevated terrain with vistas over valleys where sheep and cattle graze, arable land, and permanent grass. The landscape is characterized by its historical surroundings and picturesque rural charm.

What do other hikers say about the easy trails in Upper Winchendon?

The easy trails in Upper Winchendon are highly regarded by the komoot community, with an average rating of 4.3 stars from nearly 180 reviews. Hikers often praise the varied elevations, open countryside, and the peaceful, scenic environment.

Are there any easy circular hiking routes in Upper Winchendon?

Yes, many of the easy trails around Upper Winchendon are circular, allowing you to start and end at the same point. For example, the Windmillhill Plantation loop from Buckinghamshire is an easy 3.5-mile (5.6 km) circular path, and The Five Arrows loop from Buckinghamshire is another popular 3.2-mile (5.1 km) option.

Can I find family-friendly easy walks in Upper Winchendon?

Absolutely. The easy trails around Upper Winchendon are generally suitable for families. Many routes feature gentle terrain and manageable distances. The Grassy Field Path โ€“ River Crossing loop from Cuddington, at 2.0 miles (3.2 km), is a great option for a shorter family outing.

Are dogs allowed on the easy hiking trails around Upper Winchendon?

Most public footpaths and trails in the Buckinghamshire countryside, including those around Upper Winchendon, are dog-friendly. However, it's always recommended to keep dogs on a lead, especially when passing through fields with livestock or near roads, and to clean up after them.

What historical landmarks or points of interest can I see on an easy hike?

The area around Upper Winchendon is rich in history. You can encounter the ancient St. Mary Magdalene Church, dating back to the 12th century, which offers fine views from its elevated position. The Wilderness, a fragment of a 17th-century manor house, also adds historical interest. Additionally, the magnificent Waddesdon Manor is just 1.5 miles south of Upper Winchendon.

Are there any easy routes that pass by Waddesdon Manor?

Yes, there is an easy route that takes you through the estate. The Waddesdon Manor Collections โ€“ Waddesdon Manor loop from Buckinghamshire is a 3.5-mile (5.6 km) trail that allows you to explore the lavish grounds and car-free roads of the estate.

Are there any viewpoints on the easy trails around Upper Winchendon?

Given Upper Winchendon's elevated position, many easy trails offer scenic viewpoints over the surrounding countryside. The local church itself provides fine views. For a distinct landmark viewpoint, consider visiting Brill Windmill, which is a notable feature in the wider area.

What is the best time of year to go hiking in Upper Winchendon?

Upper Winchendon offers pleasant hiking conditions throughout much of the year. Spring and summer bring lush green landscapes and wildflowers, while autumn provides beautiful foliage. Even in winter, the trails can be enjoyed, though some paths might be muddy due to the limestone and clay soil.

Are there places to eat or drink near the easy hiking trails?

While Upper Winchendon itself is a small village, the wider area of Buckinghamshire offers options. For example, the George & Dragon in Quainton is a coffee shop and tea room that can be a convenient stop before or after your hike.

Is parking available for hikers in Upper Winchendon?

Parking in Upper Winchendon is typically available in designated areas within the village or at trailheads. As it's a rural area, specific car parks might be limited, so it's advisable to check local signage and be considerate of residents when parking.

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