![Cover image](https://images.tarmacs.app/cycling-routes/photos/united-kingdom/leicestershire-rutland-and-northamptonshire/253106980/tilton-on-the-hill-4.webp)
The Bassett Hill Challenge
A road cycling route starting from Uppingham
Take on the challenging Bassett Hill and explore picturesque villages on this epic road cycling route.
Map
![Map miniature of "The Bassett Hill Challenge" cycling inspiration in Leicestershire, Rutland and Northamptonshire, United Kingdom. Generated by Tarmacs.app cycling route planner](https://images.tarmacs.app/cycling-routes/routemaps/600/united-kingdom/leicestershire-rutland-and-northamptonshire/uppingham/road/254991.webp)
The Bassett Hill Challenge is a demanding road cycling route covering a distance of 124 kilometers with an ascent of 1063 meters. This epic route takes you through various villages and offers breathtaking views, steep climbs, and thrilling descents. Highlights along the route include Sutton Bassett with its rural charm and picturesque setting, Rupert's Viewpoint providing panoramic vistas, South Kilworth known for its scenic countryside, Street Ashton offering a glimpse into local history, Claybrooke Parva with its quaint cottages, Wigston featuring a pleasant blend of rural and urban landscapes, Tilton on the Hill with its panoramic views, and Ayston known for its traditional architecture and tranquil atmosphere.
road
124 km
1063 m
Savage
Route profile
Highlights on the route
0 km
0 km
Start: Uppingham City centerUppingham: Tranquil countryside rides near scenic Rutland Water.
Uppingham, situated in Leicestershire, Rutland and Northamptonshire, United Kingdom, offers a delightful cycling experience amidst tranquil countryside surroundings. The locality features a mix of rolling hills, charming villages, and scenic routes, making it perfect for leisurely rides. Uppingham is also known for its proximity to Rutland Water, a popular cycling destination with a dedicated cycle path encircling the reservoir. Cyclists can enjoy the serene beauty of Rutland Water while pedaling along well-maintained paths. Overall, Uppingham provides a serene and enjoyable cycling getaway for riders of all levels.16 km
16 km
Sutton BassettVillagePass through Sutton Bassett, a charming village surrounded by rolling hills and verdant landscapes.
24 km
24 km
Rupert's ViewpointViewpointTake in the breathtaking panoramic views from Rupert's Viewpoint, an elevated spot overlooking stunning natural scenery.
41 km
41 km
South KilworthVillageCycle through the picturesque countryside surrounding South Kilworth, a village known for its tranquil setting and vibrant nature.
61 km
61 km
Street AshtonHamletDiscover Street Ashton, a village that preserves its rich history with cobbled streets, historic buildings, and a timeless charm.
68 km
68 km
Claybrooke ParvaVillageExplore Claybrooke Parva, a hidden gem boasting well-preserved cottages and a tranquil, rural atmosphere.
87 km
87 km
WigstonTownRide through Wigston, a town with countryside vibes, rural landscapes, and picturesque views.
106 km
106 km
Tilton on the HillVillageMarvel at the panoramic views from Tilton on the Hill, a village perched upon an elevated position.
123 km
123 km
AystonVillageVisit Ayston, a charming village known for its traditional stone-built architecture and tranquil environment.
124 km
124 km
Finish: Uppingham City centerUppingham: Tranquil countryside rides near scenic Rutland Water.
Cycling routes nearby:
![Image of Oakham](https://images.tarmacs.app/cycling-routes/covers/united-kingdom/leicestershire-rutland-and-northamptonshire/oakham-5.webp)
![Image of Corby](https://images.tarmacs.app/cycling-routes/covers/united-kingdom/leicestershire-rutland-and-northamptonshire/corby-4.webp)
![Image of Geddington](https://images.tarmacs.app/cycling-routes/covers/united-kingdom/leicestershire-rutland-and-northamptonshire/geddington-3.webp)
![Image of Desborough](https://images.tarmacs.app/cycling-routes/covers/united-kingdom/leicestershire-rutland-and-northamptonshire/desborough-5.webp)
![Image of Stamford](https://images.tarmacs.app/cycling-routes/covers/united-kingdom/lincolnshire/stamford-3.webp)
![Image of Market Harborough](https://images.tarmacs.app/cycling-routes/covers/united-kingdom/leicestershire-rutland-and-northamptonshire/market-harborough-5.webp)
![Image of Kibworth Harcourt](https://images.tarmacs.app/cycling-routes/covers/united-kingdom/leicestershire-rutland-and-northamptonshire/kibworth-harcourt-5.webp)