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Routes
Road cycling routes
United Kingdom
England
South East England
Hampshire
Winchester

Upham

The best road cycling routes around Upham

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.

Best road cycling routes around Upham

  • The most popular road cycling…

Last updated: July 4, 2026

4.5

(4)

118

riders

#1.

Longwood Dean Lane Tree Tunnel – Old Winchester Hill loop from Fair Oak and Horton Heath

52.8km

02:25

570m

570m

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

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Moderate

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

Moderate
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18

riders

Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

Easy

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

Moderate

Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.

Moderate
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Tips from the Community

MrJulesA
May 16, 2025, Moon Roast Café

Mid week coffee is great. Not busy!

0

0

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.

1

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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.

2

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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.

2

0

Charlotte
September 1, 2024, Moon Roast Café

lovely cafe, great bacon roll

0

0

Mike
June 30, 2024, Mum's Coffee Van

Takes card and contactless payment. Recommend the Peanut Butter slice :)

0

0

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.

1

0

Frequently Asked Questions

How many road cycling routes are available around Upham?

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.

What are the typical difficulty levels for road cycling routes in Upham?

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.

What natural features and landmarks can I see while road cycling around Upham?

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.

Are there any family-friendly road cycling routes in Upham?

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.

Are there road cycling routes that offer panoramic views?

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.

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

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.

Are there circular road cycling routes available?

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.

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

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.

Are there routes that follow the River Itchen?

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.

Are there any cafes or pubs along the road cycling routes in Upham?

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.

What are some good routes for advanced road cyclists seeking a challenge?

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.

Can I combine road cycling with exploring historical sites in Upham?

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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