4.7
(126)
5,095
riders
401
rides
Road cycling routes near Whissendine traverse a landscape characterized by rolling countryside and gentle hills, providing varied terrain for cyclists. The region features well-paved surfaces suitable for road bikes, with routes ranging from leisurely rides to more challenging ascents. Natural features such as Rutland Water, Western Europe's largest man-made lake, and the Whissendine Brook contribute to the area's distinct geography. This environment offers diverse cycling experiences across its varied elevation profiles.
Last updated: July 9, 2026
64
riders
84.4km
04:12
790m
790m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
29
riders
14.9km
00:39
90m
90m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

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22
riders
18.8km
00:48
120m
120m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
13
riders
35.6km
01:32
230m
230m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
3
riders
36.8km
01:38
260m
260m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
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Some lovely bikes for purchasing. knowledgeable staff. Well stocked assortment of accessories.
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The Oakham Market Cross or Buttercross is located just behind the town’s market place, where you can buy fresh produce and various other goods every Wednesday and Saturday.
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There are over 400 road cycling routes around Whissendine, offering a wide range of options for different skill levels and preferences. The komoot community has explored these routes over 5000 times, highlighting the area's popularity for road cycling.
The terrain around Whissendine is characterized by rolling countryside and gentle hills, providing varied cycling experiences. Routes feature well-paved surfaces, with some offering leisurely rides and others presenting more challenging ascents and undulating sections. You'll find a mix of flat stretches and occasional climbs.
Yes, Whissendine offers over 120 easy road cycling routes. For example, the The Bull Climb – Edmondthorpe Drift loop from Teigh is a shorter 9.1-mile path with gentle gradients, perfect for an easier ride. Another accessible option is the Whissendine Windmill – Oakham Castle loop from Whissendine, which is 11.7 miles and leads through historic landmarks.
Many routes offer views of Rutland Water, Western Europe's largest man-made lake, which is a significant natural feature. You might also encounter the tranquil Barnsdale Bluebell Woodland, especially beautiful in spring, or cross the charming Whissendine Brook. The broader landscape features open countryside and woodlands.
Yes, several routes pass by notable landmarks. The Whissendine Windmill – Oakham Castle loop from Whissendine takes you past the historic Whissendine Windmill and Oakham Castle. You might also spot the 13th-century St Andrew's Church in Whissendine, adding cultural interest to your ride.
Along many routes, particularly around Rutland Water, you'll find pubs and cafes. The Wymondham Windmill, Tea Rooms & Windmill Wheels Bike Shop is a popular stop that caters specifically to cyclists, offering refreshments and bike services. The Horse & Jockey at Manton is another option for a break.
Yes, for more experienced riders, there are 269 moderate routes and 15 difficult routes. A notable moderate option is the Newbold Manor Sector – Owston Lane loop from Freeby, a 52.1-mile route with significant elevation gain across the rolling countryside, typically taking over 4 hours to complete.
The area is highly rated by the komoot community, with an average score of 4.7 stars from over 100 reviews. Cyclists often praise the well-paved surfaces, the varied terrain of rolling countryside and gentle hills, and the scenic views, especially around Rutland Water. The network of routes offers options for all ability levels, from easy loops to more challenging climbs.
Yes, many of the road cycling routes around Whissendine are circular, allowing you to start and end your ride in the same location. Examples include the The Bull Climb – Edmondthorpe Drift loop from Teigh and the Whissendine Windmill – Oakham Castle loop from Whissendine, both offering convenient circular journeys.
The rolling countryside and well-paved roads are enjoyable throughout much of the year. Spring, particularly late April to mid-May, offers the added beauty of the Barnsdale Bluebell Woodland in full bloom. Summer and early autumn generally provide pleasant weather conditions for cycling, though local weather patterns should always be checked.
Yes, the region around Whissendine is known for its quiet country lanes. Many cycling routes are specifically designed to avoid heavy traffic, providing a more enjoyable and safer experience through the picturesque rolling countryside and charming villages.
While road cycling typically involves open roads, some of the easier, shorter loops with gentle gradients can be suitable for families with older children comfortable on roads. The area's quiet country lanes also contribute to a more relaxed cycling environment. Always assess the specific route's traffic levels and your family's comfort with road cycling.


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