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Road cycling routes
United Kingdom
England
East Midlands
Rutland

Whissendine

The best road cycling routes around Whissendine

4.6

(132)

4,952

riders

384

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.

Best road cycling routes around Whissendine

  • The most popular…

Last updated: August 19, 2026

55

riders

#1.

Whissendine Level Crossing – Owston Lane loop from Freeby

84.0km

04:11

790m

790m

Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.

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Moderate

Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

Easy
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Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

Easy

Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

Easy

Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

Easy
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Tips from the Community

Derren
August 19, 2025, Sigma Sports

Some lovely bikes for purchasing. knowledgeable staff. Well stocked assortment of accessories.

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St Andrew's Church is the Church of England parish church of Hambleton, Rutland. It is a Grade II* listed building.

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The village stands on the Hambleton Peninsula between arms of the Rutland Water reservoir.

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Really helpful staff - worth just going in for a chat!

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Alex Boulting
April 1, 2025, Fika Cafe

Great Cafe with vege options

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on_one
March 29, 2025, Fika Cafe

Outstanding coffee! Great for a mid ride snack

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The castle was built between 1180 and 1190 by Walkelin de Ferrers, lord of the manor of Oakham, and a great nephew of Robert de Ferrers, 1st Earl of Derby.[1] The Great Hall comprises a nave and two arcaded aisles, each with three large stone columns. There are a number of 12th-century sculptures decorating the hall including six musicians that are supported by the columns. The sculptures are carved from local stone quarried at Clipsham and are believed to have been made by masons who had also worked at Canterbury Cathedral.[2]

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Darren
October 6, 2024, Fika Cafe

Lovely little breakfast stop, great coffee and really good spicy beans !

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Frequently Asked Questions

How many road cycling routes are available around Whissendine?

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.

What kind of terrain can I expect on road cycling routes near Whissendine?

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.

Are there road cycling routes suitable for beginners or those looking for an easy ride?

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.

What natural features can I see along the road cycling routes?

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.

Are there any historical landmarks or points of interest along the cycling routes?

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.

Where can I find places to stop for refreshments or bike services?

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.

Are there any longer or more challenging road cycling routes for experienced riders?

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.

What do other road cyclists enjoy most about cycling in Whissendine?

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.

Are there circular road cycling routes available?

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.

When is the best time of year for road cycling in Whissendine?

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.

Are there quiet country lanes for cycling, away from heavy traffic?

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.

Can I find family-friendly road cycling routes in the area?

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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