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United Kingdom
England
South East England
Buckinghamshire
Aylesbury Vale

Upper Winchendon

The best walks and hikes around Upper Winchendon

4.3

(181)

1,822

hikers

207

hikes

Hikes around Upper Winchendon explore the rolling countryside of Buckinghamshire. The landscape is characterized by gentle hills, agricultural fields, and sections of woodland, with trails often following public footpaths between small villages. The routes in this area are primarily on well-defined paths, offering walks through a rural English setting.

Best hiking trails around Upper Winchendon

  • The most popular hiking route is Waddesdon Estate Parking – Waddesdon Hill loop from Waddesdon, a 5.3 mile (8.5 km) trail that takes around…

Last updated: April 23, 2026

3.5

(4)

10

hikers

#1.

Waddeston Estate to Chearsley circular

24.4km

06:30

270m

270m

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

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Hard

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

Moderate
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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

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

Moderate
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Popular around Upper Winchendon

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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, Village Stocks, Dinton

A cross between stocks and a pillory?

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

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A bridge spans over a small tributary of the River Thames next to a waterfall, creating a beautiful scene as you jog past.

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Frequently Asked Questions

Are there many hiking trails to choose from around Upper Winchendon?

Yes, there's a wide variety of options. You can explore nearly 190 different hiking routes in the region, with over 100 of them rated as easy, making it accessible for all skill levels.

What do other hikers think of the trails in this area?

The trails around Upper Winchendon are well-regarded by the komoot community. With over 1,600 visitors sharing their experiences, the routes have earned a high average rating. Hikers often praise the gentle rolling hills and quiet paths through the Buckinghamshire countryside.

Are there any good circular walks available?

Absolutely. Many trails in the area are loops, starting and finishing in the same place. For a shorter, accessible loop, the Waddesdon Manor Collections – Waddesdon Manor loop from Buckinghamshire is a great option that explores the grounds of the historic estate.

Can I bring my dog on the trails near Upper Winchendon?

Yes, the region is generally dog-friendly, with many public footpaths crossing open countryside where dogs are welcome. However, you will likely cross fields with livestock, so it's essential to keep your dog on a lead in these areas. Always check for local signage regarding dog policies.

Are there any easy, family-friendly walks?

The area is perfect for family outings. You'll find many gentle, easy-rated trails suitable for all ages. The Windmillhill Plantation loop from Buckinghamshire is a pleasant walk of about 3.5 miles through mixed farmland and woodland that is great for a relaxed afternoon.

Where can I find hikes with the best views?

For expansive, panoramic views, local hikers often head to Pitstone Hill. It's a highly-regarded spot known for its pristine scenery across the surrounding landscape. The trails there are clearly marked, allowing you to focus on the beautiful surroundings.

Is it possible to go for a long-distance hike in this region?

Yes, the area caters to long-distance hikers. For a challenging day out, the Waddeston Estate to Chearsley circular is a demanding 15-mile route that connects several villages and offers a comprehensive tour of the local landscape.

Are there any trails that go past a waterfall?

Yes, you can find a route that features a waterfall. The Waterfall at Stone Arch Bridge – Headless Stone Sculpture loop from Buckinghamshire is a moderate 6.4-mile hike that takes you past this pleasant water feature as part of a scenic walk.

What are some popular places for hiking near Upper Winchendon?

The region is part of a beautiful landscape with several popular hiking destinations.

The Chilterns National Landscape is a vast area offering numerous hiking and cycling trails through classic English countryside. For more focused walks, the National Trust - Chilterns Countryside provides well-maintained hilltop paths with extensive views over Buckinghamshire. Another favorite is Pitstone Hill, celebrated for its stunning panoramic vistas.

Where can I find a good walk in a nature reserve?

The Weston Turville Reservoir Nature Reserve is a beautiful place for a peaceful walk. It offers a circular trail around the reservoir where you can enjoy watching for birds and other wildlife. The paths are well-suited for a relaxing stroll in a natural setting.

Is it easy to find parking for the walks?

Many popular trailheads, especially those starting near villages or attractions like Waddesdon Manor, have designated parking areas. For example, the Waddesdon Estate Parking – Waddesdon Hill loop from Waddesdon begins from a car park. For walks starting in smaller villages, on-street parking may be available, but always be sure to park considerately.

Can I reach the hiking trails using public transport?

Accessing trailheads via public transport can be challenging as the area is quite rural. Your best option is to take a train to a nearby town like Aylesbury and then use a local bus service to get closer to villages like Waddesdon or Cuddington. It is advisable to check bus timetables in advance as services may be infrequent.

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