4.7
(450)
13,273
riders
363
rides
Road cycling around Upham offers diverse landscapes, primarily on paved surfaces, suitable for various skill levels. The region is situated near the South Downs National Park, providing scenic backdrops and varied terrain. Prominent features include St Catherine's Hill and Old Winchester Hill, both offering elevated views of the surrounding countryside. The area is also characterized by the River Itchen, an important chalk stream, and historic estates like Avington Park.
Last updated: July 4, 2026
4.5
(4)
118
riders
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
26
riders
60.2km
02:39
550m
550m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

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18
riders
9.40km
00:24
80m
80m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
10
riders
47.8km
02:07
460m
460m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
10
riders
31.9km
01:32
340m
340m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
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beautiful views of the surrounding country and loads of wildlife spotting
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Cheriton is a stunning Hampshire village. It houses a beautiful old church and Cheriton Post Office and Stores, which is a great place to stop and restock refreshments.
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This is a stunning tree-lined road where the trees arch toward each other, forming a natural canopy overhead as you cycle through.
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Longwood Dean Lane is a beautiful back country lane just east of Owslebury. It is a stunning tree lined lane with the glimpses of open country in places. It’s a great connecting road to connect Belmore Lane and Lane End. Simply a beautiful stretch of road.
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Takes card and contactless payment. Recommend the Peanut Butter slice :)
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Wheely Down Farm Lane is a fabulous road with wonderful ridge top views as far as the English Channel. It runs parallel to the route of the South Downs Way, a long distance cycling and walk National Trail from Winchester to Eastbourne. It's a smooth road offering a steady climb (or descent) without much traffic to contend with.
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Upham offers a wide selection of road cycling routes, with over 300 options available. These routes cater to various skill levels, ensuring there's something for everyone from beginners to experienced cyclists.
The routes around Upham are categorized into easy, moderate, and difficult. You'll find approximately 120 easy routes, over 210 moderate routes, and about 10 more challenging options, providing a good range for all abilities.
The Upham area is rich in natural beauty and historical sites. You can cycle past significant landmarks such as Old Winchester Hill, an Iron Age hill fort offering expansive views, and St Catherine's Hill, another prominent chalk downland with an Iron Age fort. The tranquil The Weirs in Winchester along the River Itchen, and the picturesque Avington Park Mansion and Lake are also notable points of interest.
Yes, Upham offers numerous family-friendly road cycling routes, with over 120 easy options. These routes typically feature less elevation gain and are suitable for a more relaxed pace, allowing families to enjoy the scenic countryside together.
Absolutely. Many routes in the Upham area, particularly those traversing the South Downs National Park, provide breathtaking panoramic views. Routes that pass Old Winchester Hill and St Catherine's Hill are excellent choices for cyclists seeking elevated vistas over the surrounding countryside and the Itchen Valley.
The Upham area is generally pleasant for road cycling from spring through autumn. The mild weather and vibrant landscapes make these seasons ideal. While winter cycling is possible, be prepared for cooler temperatures and potentially wet conditions, especially on less sheltered routes.
Yes, many of the road cycling routes around Upham are designed as loops, allowing you to start and finish in the same location. For example, the "Longwood Dean Lane Tree Tunnel – Old Winchester Hill loop from Fair Oak and Horton Heath" is a popular circular option that takes you through diverse scenery.
The road cycling experience in Upham is highly rated by the komoot community, with an average score of 4.7 stars from over 400 reviews. Cyclists frequently praise the diverse landscapes, the quiet roads, and the stunning views from prominent hills like Old Winchester Hill and St Catherine's Hill.
Yes, the River Itchen is a significant natural feature in the area, and some road cycling routes incorporate sections alongside it. These routes offer a serene environment with opportunities to observe local wildlife. The "Bishops Waltham Pond – River Itchen loop from Bishop's Waltham" is one such route that allows you to experience the river's charm.
While specific establishments are not detailed in route descriptions, the villages and towns surrounding Upham, such as Bishop's Waltham and Winchester, offer various cafes and pubs where cyclists can refuel and rest. Many routes are designed to pass through or near these amenities.
For advanced road cyclists, routes with significant elevation gain and longer distances will provide a good challenge. While there are about 10 routes specifically rated as difficult, many of the moderate routes, such as the "Longwood Dean Lane Tree Tunnel – Longwood Dean Lane loop from Upham" with over 500 meters of ascent, can also offer a demanding ride.
Absolutely. The Upham area is rich in history, and many road cycling routes pass by or near historical sites. Both Old Winchester Hill and St Catherine's Hill are sites of Iron Age hill forts, offering a chance to combine your ride with a visit to ancient landmarks.


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