4.5
(75)
2,609
riders
111
rides
Road cycling routes around Winstone are situated within the Cotswolds, a designated Area of Outstanding Natural Beauty in Gloucestershire, England. The region is characterized by rolling hills, valleys, limestone villages, and ancient woodlands, providing a varied terrain for cyclists. Routes feature a mix of gentle ascents and descents through open countryside.
Last updated: July 10, 2026
4.0
(2)
66
riders
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
4.0
(2)
42
riders
34.7km
01:52
300m
290m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

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17
riders
37.3km
02:25
770m
770m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
19
riders
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
12
riders
82.0km
03:52
540m
530m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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At the General Audience on June 21, 2006, the then Holy Father briefly summarized two biblical accounts that illustrate the special position of James the Greater, the patron saint of this church, among the disciples: "He was privileged, along with Peter and John, to participate in the hour of Jesus' agony in the Garden of Gethsemane and in the event of Jesus' transfiguration. (...) In the first instance, James, together with the other two apostles, experienced the glory of the Lord; he saw him speaking with Moses and Elijah; he saw the radiance of divine glory shine forth in Jesus; in the second instance, he stood before suffering and humiliation; he saw with his own eyes how the Son of God humbled himself and was obedient unto death. The second experience was certainly an opportunity for him to mature in faith and to correct the one-sided, triumphalistic interpretation of the first experience: He had to recognize that the Messiah, whom the Jewish people expected to be a triumphant figure, was in reality not only surrounded by honor and glory, but also of suffering and weakness. The glory of Christ is realized precisely on the cross, in sharing in our sufferings.” (Pope Benedict XVI)
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Marks the junction to take Sherborne St climb towards Bourton on the Water which is a lovely road to take.
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Watch out for tourists wandering into the road!!
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Arrive before 12 for a great bacon baguette! V60 coffee is the best too!
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"The Anglican Church of St James at Coln St. Dennis in the Cotswold District of Gloucestershire, England, was built in the 12th century. It is a grade I listed building. The Church of England parish church is dedicated to Saint James the Great. The church was dedicated to Saint Katherine in the 13th century, Saint Dennis in the 18th century, and is believed to have once been dedicated to Saint Kenelm.[2] During the 18th century it may have briefly been dedicated to St Dennis. The central tower had a belfry added in the 15th century. This was rebuilt in 1904 as part of a wider restoration by William Weir the architect for the Society for the Protection of Ancient Buildings. The parish is part of the Chedworth Yanworth and Stowell Coln Rogers and Coln St Dennis benefice within the Diocese of Gloucester." Source: https://en.m.wikipedia.org/wiki/Church_of_St_James,_Coln_St._Dennis
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You feel like you've been transported back a few centuries and are reminded of Little Lord Fauntleroy...
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Personally found it quite alright on 28mm road tyres, just pay a little bit more attention to the surface.
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Very popular with tourists. In particular those from Japan as apparently Emperor Hirihito once stayed in Bibury as he conducted his European tour.
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Road cycling around Winstone, nestled in the Cotswolds, features a diverse landscape of rolling hills, valleys, and open countryside. You'll encounter a mix of gentle ascents and descents, characteristic of the region's limestone villages and ancient woodlands. Routes can range from moderate to more challenging, with some offering significant elevation gain.
There are over 110 road cycling routes available around Winstone. These routes cater to various skill levels, including 32 easy, 74 moderate, and 8 difficult options, ensuring there's something for every cyclist.
Yes, there are several easy routes. For instance, the Cirencester Market Place – Cafe Mosaic loop from Duntisbourne Abbots is an easy 21.5-mile (34.7 km) path that winds through open fields with gentle terrain, perfect for those new to road cycling or looking for a relaxed ride.
Many routes offer beautiful scenery through the Cotswolds. The Coln River Villages, Cotswolds – Arlington Row, Bibury loop from Duntisbourne Abbots is a popular moderate route that passes through picturesque Cotswolds villages and scenic landscapes. Another option is the Windrush Valley Country Lane – View of the Cotswolds Valley loop from Duntisbourne Abbots, which offers expansive views.
Absolutely. For experienced cyclists seeking a challenge, the Wishanger Lane – Sheepscombe Climb loop from Winstone is a 22.9-mile (36.9 km) trail that leads through rolling hills with significant elevation gain. The wider Cotswolds region also offers routes with notable climbs and varied terrain.
The routes often pass through charming limestone villages with honey-coloured cottages and ancient churches. You can also find natural features like the Painswick Beacon, offering rewarding views, or the unique Devil's Chimney, Leckhampton Hill. Many routes traverse expansive open countryside and ancient woodlands.
Yes, many of the road cycling routes around Winstone are designed as loops, allowing you to start and finish at the same point. Examples include the Vicarage Lane – Quiet Country Lane loop from Duntisbourne Abbots, which is a moderate 81.8 km route.
The road cycling routes in Winstone are highly rated by the komoot community, with an average score of 4.4 stars from over 60 reviews. More than 2,500 road cyclists have used komoot to explore the varied terrain, often praising the scenic beauty of the Cotswolds and the well-maintained paths.
While many routes involve rolling hills, there are easier sections and less trafficked country lanes that can be suitable for families. Look for routes categorized as 'easy' or those that stick to flatter sections through villages and open fields for a more relaxed family ride.
Yes, the Cotswolds region is known for its charming villages, many of which feature traditional pubs and cafes. While specific establishments aren't listed for every route, planning your ride through villages like Bibury or Cirencester (as seen in routes like the Cirencester Market Place – Cafe Mosaic loop) will likely offer opportunities for refreshments.
The spring and summer months (April to September) generally offer the most pleasant conditions for road cycling in Winstone, with milder weather and longer daylight hours. Autumn can also be beautiful with changing foliage, though cooler temperatures and potential rain should be considered. Winter cycling is possible but requires appropriate gear for colder, potentially wetter conditions.


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