4.5
(111)
1,515
riders
159
rides
Touring cycling around Upper Winchendon features a landscape of gentle rolling hills, open farmland, and historic villages. The region is characterized by quiet country lanes and dedicated greenways, offering a mix of easy touring bike trails and more moderate routes. Many circular bike routes in Upper Winchendon explore the local heritage and natural beauty of Buckinghamshire.
Last updated: July 2, 2026
3.5
(4)
31
riders
28.0km
01:55
250m
250m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
4.3
(3)
33
riders
Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.

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13
riders
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
4.5
(2)
12
riders
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5.0
(1)
12
riders
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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Take a detour and have a drink at Thame. Well worth it.
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In the summer there are tours for Β£3 donation from 2pm on Sunday
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Do you need to be a NT member for this?
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Some stunning views across he fields towards Whiteleaf Cross
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Nice ride along very smooth tarmac in the Chilterns a wonderful spot just outside of London, the Chilterns seem to get less love than the Surrey Hills but they are a wonderful place to ride.
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There are over 160 touring cycling routes in the Upper Winchendon area, offering a wide variety of options for different skill levels and preferences. You'll find everything from easy, flat rides to more challenging routes with moderate elevation gains.
Yes, Upper Winchendon offers many easy touring cycling routes, with over 50 routes classified as easy. These often follow quiet country lanes and dedicated greenways, making them ideal for beginners or families. The region's landscape of gentle rolling hills is generally very accessible.
The touring cycling routes around Upper Winchendon feature a landscape of gentle rolling hills, open farmland, and historic villages. You'll primarily ride on quiet country lanes and dedicated greenways, providing a pleasant and varied experience.
Many of the touring cycling routes in Upper Winchendon are circular, allowing you to start and finish at the same point. An example is the Waddesdon Greenway loop from Westcott, which is a popular 17.3-mile (27.9 km) option.
The routes often pass by historic sites and scenic viewpoints. You might encounter landmarks like Brill Windmill or the impressive Waddesdon Manor. The Historic Buildings of Thame β Brill Windmill loop from Haddenham and Thame Parkway specifically highlights some of the area's rich heritage.
Yes, while many routes are gentle, there are also more challenging options. Over 20 routes are classified as difficult, featuring more significant elevation gains. For instance, the Upper Winchendon Climb β Cannon's Hill Climb loop from Aylesbury Vale Parkway includes notable ascents.
Yes, the region's historic villages often have pubs and cafes. For example, the George & Dragon β Coffee Shop & Tea Room in Quainton is a popular stop. Many routes pass through or near villages where you can refuel.
The best seasons for touring cycling in Upper Winchendon are generally spring, summer, and early autumn. During these months, the weather is typically milder, and the countryside is at its most vibrant. Always check the local forecast before heading out.
Absolutely. The region benefits from dedicated greenways. The Hay Field β Waddesdon Greenway loop from Haddenham and Thame Parkway is a great example, connecting to the popular Waddesdon Greenway, which offers a car-free cycling experience.
Route durations vary significantly based on distance and your pace. For example, the Lacey Green Windmill β Phoenix Trail loop from Haddenham and Thame Parkway, at nearly 50 km, can take over 3.5 hours, while shorter routes might be completed in under 2 hours.
Yes, some routes are conveniently accessible via public transport. Several popular loops, such as the Historic Buildings of Thame β Brill Windmill loop, start from Haddenham and Thame Parkway, which is a train station, making it easy to reach without a car.
The touring cycling routes in Upper Winchendon are highly rated by the komoot community, with an average score of 4.4 stars from over 100 reviews. Cyclists often praise the quiet country lanes, the scenic views of open farmland, and the charm of the historic villages.


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