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Routes
Road cycling routes
United Kingdom
England
East Midlands
Rutland

Uppingham

The best road cycling routes around Uppingham

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.

Best road cycling routes around Uppingham

  • The most popular road cycling route is Empingham Village – Lyndon Village…

Last updated: May 12, 2026

32

riders

#1.

Empingham Village – Lyndon Village loop from Uppingham

41.6km

02:09

440m

440m

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

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Moderate

Moderate road ride. Great for any fitness level. Some segments of this route may be unpaved and difficult to ride.

Moderate
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Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate

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

ACW2018%
April 1, 2026, Old White Hart Pub, Lyddington

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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Derren
August 19, 2025, Sigma Sports

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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Ben
July 21, 2025, Empingham Village

Good place to ride - nice and hilly!

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Must see viaduct just amazing

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Very impressive viaduct. You arrive there when you pass into Rutland area.

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Paul
April 25, 2025, Lyndon Village

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

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Frequently Asked Questions

How many road cycling routes are available around Uppingham?

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.

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

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'.

Are there easy road cycling routes suitable for beginners or families in Uppingham?

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.

What scenic landmarks or attractions can I see while road cycling around Uppingham?

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.

Are there any challenging road cycling routes for experienced riders?

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.

Where can I find places for a break or refreshments along the road cycling routes?

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.

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

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.

Are the road cycling routes around Uppingham mostly circular?

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.

Which route is recommended for experiencing Rutland Water?

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.

Is there a route that features the Welland Viaduct?

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.

What is the best time of year for road cycling in Uppingham?

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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