4.7
(9)
889
riders
72
rides
Road cycling routes around Shipston On Stour are situated on the northern edge of the Cotswolds, offering a landscape of rolling hills and the rural Stour Valley. The area is characterized by quiet country lanes that traverse picturesque countryside. This region provides a diverse backdrop for road cycling, with routes often featuring gentle to moderate climbs through patchwork fields and small villages.
Last updated: May 14, 2026
5.0
(1)
82
riders
49.5km
02:19
270m
270m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
69
riders
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

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4.0
(2)
47
riders
39.8km
01:57
230m
230m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
4.0
(1)
37
riders
41.4km
01:50
250m
250m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
27
riders
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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The Rev Cafe lives on in Stow on the Wold, located in Talbot Court.
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This Cycle shop and cafe is now permanently closed
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Chesteron Windmill was built in 1632 and is one of the oldest surviving windmills in England. It was originally used for grinding corn and has a rich history ties to the agricultural practices of the region.
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Moreton Paddox was the name of a country manor house which stood in this area until 1959 when it was demolished. It was a grand house with formal gardens and an ornamental lake, although little evidence remains.
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Edgehill Castle (Tower) which is now a rather nice pub/restaurant. The castle was built in the 18th Century as a 'sham' castle reputedly on the exact spot where Charles I raised his standard before the Battle of Edgehill during the first English Civil War. Apparently Cromwell got there too late for the battle.
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The area around Shipston-on-Stour, situated on the northern edge of the Cotswolds, features a landscape of rolling hills and the rural Stour Valley. You'll primarily ride on quiet country lanes, traversing picturesque countryside with gentle to moderate climbs through patchwork fields and small villages. The routes offer varied scenery, from the distinctive 'wolds' of the Cotswolds to the meandering River Stour.
Yes, the routes around Shipston-on-Stour cater to various abilities. Out of approximately 70 available routes, 22 are classified as easy, 45 as moderate, and 5 as difficult. For example, the The Peacock Public House – Tysoe Village loop from Shipston-on-Stour is an easy 25-mile ride, while the La Tradition French Bakery – St George's Church loop from Shipston-on-Stour is a moderate 36.7-mile path with over 450 meters of ascent.
While cycling, you can enjoy the distinctive rolling hills of the Cotswolds and the serene River Stour Valley. Notable landmarks include Brailes Hill, an outlying Cotswold feature, and historic sites like the King Stone and the Rollright Stones Stone Circle, ancient monuments made of oolitic limestone. You might also pass through charming market towns like Moreton-in-Marsh.
The spring, summer, and early autumn months generally offer the most pleasant conditions for road cycling in the Cotswolds. During these seasons, you can expect milder weather, longer daylight hours, and the countryside to be in full bloom or displaying rich autumnal colours. While winter cycling is possible, be prepared for colder temperatures and potentially wet or icy roads.
Yes, many of the road cycling routes around Shipston-on-Stour are designed as loops, allowing you to start and finish in the same location. An example is the popular Tysoe Village – Kineton War Memorial loop from Shipston-on-Stour, a 30.8-mile route through rural Warwickshire.
The area is highly rated by the komoot community, with an average score of 4.7 stars from over 8 reviews. Cyclists often praise the quiet country lanes, the varied and picturesque scenery, and the manageable ascents through charming villages and patchwork fields. Over 800 road cyclists have used komoot to explore this diverse terrain.
Yes, the region offers options for longer rides. The 'Shipston to Southam Cycle Route' follows National Cycle Network Route 48, traversing stunning countryside for approximately 28 miles between the Cotswold Area of Outstanding Natural Beauty and the Warwickshire Feldon. This route also includes a spur to Burton Dassett Hills Country Park, known for its views.
Shipston-on-Stour itself is a thriving historic market town and serves as an excellent base for exploring the region. You can typically find public parking within the town, which allows convenient access to the start of many local road cycling routes. Always check local signage for parking regulations and fees.
While many routes are on quiet country lanes, the 'Two Towns Cycle Route' is an 8-mile path linking Shipston-on-Stour with Moreton-in-Marsh. This route showcases attractive Saxon-era towns and heritage buildings, and its shorter distance might be more suitable for families looking for a less strenuous ride. Additionally, there are 22 easy-rated routes available on komoot.
Yes, the area is known for its charming villages and market towns, which often feature independent shops, cafes, and pubs. The local cycling club, 'Shipston Cycling,' even organizes social rides with café stops, indicating that such amenities are readily available along many routes for a refreshing break.
The routes around Shipston-on-Stour are characterized by rolling hills, meaning you can expect gentle to moderate climbs. For instance, the Pillerton Hersey Church – Tysoe Village loop from Shipston-on-Stour, an easy 41.3 km route, has an elevation gain of over 250 meters. More challenging routes, like the Chesterton Windmill – View of Chesterton Windmill loop from Shipston-on-Stour, can feature over 500 meters of ascent.
Absolutely. The area is rich in history. You can cycle to the Rollright Stones, a complex of Neolithic and Bronze Age monuments including the King Stone, the King's Men Stone Circle, and the Whispering Knights Dolmen. These sites offer a unique historical outdoor experience.


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