4.4
(111)
5,061
riders
329
rides
Road cycling routes around Upper Winchendon are characterized by varied terrain, situated on high ground with elevations generally around 400 feet. The surrounding landscape features extensive agricultural land, including permanent grass and arable fields, offering open countryside views. Gentle undulations and descents to 300 feet in some areas provide diverse cycling experiences. The region's limestone and clay soil contribute to its distinct rural environment.
Last updated: May 16, 2026
3.0
(1)
14
riders
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
5.0
(2)
13
riders
28.0km
01:17
220m
220m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

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5.0
(1)
13
riders
23.8km
01:07
300m
300m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
7
riders
59.9km
02:40
480m
480m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
4
riders
18.1km
01:22
190m
190m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
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Lovely and quiet once past the main estate road.
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This lovely country road travels through the charming village of Bishopstone and allows you to soak up wide open spaces and far-reaching views. There is a nearby pub called The Harrow which is a great place to refuel.
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A lovely little church, didn't get a chance to go inside by was nice to take a stop at
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A beautiful section of cycling through the Waddesdon Estate, a historic estate purchased and maintained by the Rothschild family.
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Great spot for a coffee, cake or bacon sandwich with scandinavian twist. Character inside and with wooden seating in the back yard. The quality of the food is excellent
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Dinton is a charming little village situated in the south of the Aylesbury Vale on the ancient turnpike leading from Aylesbury to Thame. In the village you'll find an old folly, a converted castle, and a beautiful pub, Bottle & Glass.
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Looks like great gentle cycling - can anyone please recommend a good circular route on predominately car free roads?
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A fine example of a pretty Bucks village. Old stone walls, a medieval church - what more could you want?!
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There are over 300 road cycling routes around Upper Winchendon listed on komoot, offering a wide range of options for different skill levels and preferences.
Yes, Upper Winchendon offers over 100 easy road cycling routes. An excellent option is the Hartwell Church Ruins β Sprint Segment loop from Stone with Bishopstone and Hartwell, an easy 17.4 km trail that takes about 44 minutes to complete and features a pleasant sprint segment through the countryside.
The terrain around Upper Winchendon is characterized by varied landscapes, situated on high ground generally around 400 feet, with descents to 300 feet. You'll find gentle undulations, open agricultural fields, and some more challenging climbs, all contributing to a diverse cycling experience. The area's limestone and clay soil also add to its distinct rural environment.
Yes, for those seeking a challenge, there are 10 difficult road cycling routes available. Additionally, many moderate routes, such as the Cannon's Hill Climb β Chilton Village loop from Westcott, offer significant elevation gains over longer distances, providing a good workout.
The Waddesdon Manor Estate Car-Free Roads are highly recommended. These well-maintained, private roads offer a gorgeous ride through beautiful fields, providing a safe and picturesque environment for cyclists. The estate itself is just 1.6 miles from Upper Winchendon.
Yes, the George & Dragon in Quainton is a popular spot among local cyclists. It offers coffee, cakes, and even a water tap for refilling bidons, making it an ideal stop along a scenic route through the Waddesdon Estate.
The area is rich in history. You can visit Waddesdon Manor, known for its lavish grounds and architecture. The historic Church of St Mary Magdalene in Upper Winchendon, dating back to 1120, is also a notable sight. Additionally, Nether Winchendon House, a Grade I listed Medieval and Tudor manor, offers tranquil gardens and parkland views.
The area is highly rated by the komoot community, with an average score of 4.4 stars from over 90 reviews. Cyclists often praise the picturesque landscapes, varied terrain, and the charming rural character, including the open countryside views and the quiet lanes.
Yes, several routes feature significant climbs. For example, the Cannon's Hill Climb β Upper Winchendon Climb loop from Buckinghamshire is an easy 28.0 km path that includes a notable hill climb, offering a moderate challenge with scenic views.
Yes, there are options for longer rides. The Cannon's Hill Climb β Chilton Village loop from Westcott is a moderate 59.8 km route that takes approximately 2 hours and 40 minutes to complete, offering a substantial ride through the region.
Many of the routes in Upper Winchendon are circular, allowing you to start and end in the same location. An example is the View of the Countryside β Chilton Village loop from Westcott, a 23.8 km trail leading through open agricultural land.
The village of Upper Winchendon itself is situated on high ground, with the Church of St Mary Magdalene offering fine views over the valley. Additionally, the Brill Windmill is a prominent landmark and viewpoint in the wider area, offering panoramic vistas that can be incorporated into a cycling route.


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