The best road cycling routes in Rutland
4.7
(121)
5,534
riders
377
rides
Last updated: October 21, 2025
6
riders
1. Rutland County Boundaries loop
106km
05:01
910m
910m
Expert road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.
5.0
(6)
957
riders
2. Rutland Water South Shore – Giant Store Rutland Water loop from Whitwell
33.8km
01:56
200m
200m
Intermediate road ride. Great for any fitness level. Some segments of this route may be unpaved and difficult to ride.
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4.6
(5)
113
riders
3. Lyndon Village – Red Lion Square, Stamford loop from South Luffenham
46.3km
02:08
350m
350m
Intermediate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
5.0
(5)
92
riders
Intermediate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
75
riders
5. Newbold Manor Sector – Owston Lane loop from Oakham
92.9km
04:24
860m
860m
Intermediate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
76
riders
6. Seaton Hill Climb – Welland Viaduct loop from South Luffenham
50.3km
02:24
350m
350m
Intermediate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
70
riders
7. Sigma Sports – Sludge Hall Hill loop from Oakham
64.3km
03:10
690m
690m
Intermediate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
4.6
(11)
66
riders
8. Oakham Castle – Windmill Wheels Bike Shop loop from Oakham
41.2km
01:41
200m
200m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
5.0
(3)
153
riders
9. Oakham Castle – Empingham Village loop from Oakham
27.2km
01:08
180m
180m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
5.0
(2)
42
riders
10. Oakham Castle – Empingham Village loop from Whitwell
41.2km
02:00
280m
290m
Intermediate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
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Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.
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