5.0
(10)
323
riders
33
rides
Road cycling around Uppingham is characterized by its gently rolling countryside and scenic beauty within Rutland. The region features a mix of flat stretches and moderate climbs, with mostly paved surfaces ideal for road bikes. A prominent natural feature is Rutland Water, offering dedicated cycle routes with continuous views. The area also includes charming villages and impressive structures like the Welland Viaduct.
Last updated: May 12, 2026
32
riders
41.6km
02:09
440m
440m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
26
riders
19.9km
01:07
250m
250m
Moderate road ride. Great for any fitness level. Some segments of this route may be unpaved and difficult to ride.

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5.0
(1)
18
riders
44.2km
02:20
500m
500m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
5.0
(1)
17
riders
72.2km
03:14
560m
560m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
5.0
(2)
17
riders
21.6km
01:14
250m
250m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
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Beautiful pub, open 7 days a week offering food and accommodation. stopped off for a quick refreshment in the beer garden.
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Some lovely bikes for purchasing. knowledgeable staff. Well stocked assortment of accessories.
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Well worth the stop to admire the exterior of both buildings, and the uplifting interior of St Andrews. Love the Angels and look for the painting of Edward the Confessor
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Very impressive viaduct. You arrive there when you pass into Rutland area.
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Picks Barn is a great place for coffee and a bite to eat although it’s not open on Monday and Tuesday
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There are over 30 road cycling routes available around Uppingham, catering to various preferences and skill levels. These routes have been explored and shared by more than 300 road cyclists in the komoot community.
Road cycling around Uppingham features gently rolling countryside with a mix of flat stretches and moderate climbs. The routes primarily consist of paved surfaces, making them ideal for road bikes. You'll experience the scenic beauty of Rutland, often referred to as 'the playground of the East Midlands'.
Yes, Uppingham offers several easy road cycling routes perfect for beginners or families. There are 12 easy routes available, providing a gentle introduction to the area's beautiful landscapes. These routes often feature less elevation gain and are designed for a more relaxed pace.
Many routes offer stunning views and pass by notable landmarks. You can cycle past the iconic Normanton Church, which appears to 'float' on Rutland Water, or marvel at the impressive Welland Viaduct. Routes like the Empingham Village – Lyndon Village loop offer continuous views of Rutland Water and pass through picturesque villages.
While Uppingham's terrain is generally gently rolling, there are 21 moderate routes that offer more challenge for experienced riders. For example, the Uppingham School – King's Hill Climb loop includes a notable climb and provides expansive views, testing your endurance.
The charming villages and market towns around Uppingham are perfect for mid-ride breaks. Many routes pass through these areas, offering traditional pubs and cafes where you can stop for refreshments or a pub lunch. Uppingham itself is an acclaimed market town with various options.
The road cycling routes in Uppingham are highly rated by the komoot community, with an average score of 5.0 stars from over 10 reviews. Cyclists often praise the region's scenic beauty, the well-maintained paved surfaces, and the variety of routes that cater to different fitness levels, especially those incorporating Rutland Water and charming villages.
Yes, many of the road cycling routes around Uppingham are designed as loops, allowing you to start and finish in the same location. Examples include the Empingham Village – Lyndon Village loop and the Normanton Church – Empingham Village loop, providing convenient circular journeys.
To experience Rutland Water, the Normanton Church – Empingham Village loop from Uppingham is an excellent choice. This 44.8-mile (72.2 km) route leads directly through the Rutland Water area, offering continuous scenic views and passing by the iconic Normanton Church.
Yes, the Welland Viaduct – Exeter Arms loop from Uppingham is an easy 21.5-kilometer (13.4-mile) route that incorporates this impressive engineering marvel. Another option is the Uppingham School – Welland Viaduct loop, a moderate 33-kilometer (20.5-mile) ride.
Uppingham's gently rolling terrain and mostly paved surfaces make it suitable for road cycling through much of the year. Spring and summer offer pleasant weather and vibrant landscapes, while autumn provides beautiful foliage. Always check local weather conditions before heading out, especially during winter months.


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