4.5
(48)
2,552
riders
11
rides
Road cycling around Medstead offers a diverse landscape characterized by rolling hills, woodlands, and picturesque country lanes within Hampshire. The region provides a mix of terrains, with many routes featuring mostly paved surfaces suitable for various skill levels. Cyclists can explore areas like the "Hampshire Hangers" and routes incorporating Chawton Woods and the River Itchen. This varied topography makes Medstead a suitable base for both leisurely rides and more challenging excursions.
Last updated: May 23, 2026
5.0
(1)
55
riders
47.0km
02:03
430m
430m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
14
riders
75.8km
03:37
800m
800m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.

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23
riders
63.8km
02:41
470m
470m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
5.0
(1)
8
riders
19.2km
00:48
130m
130m
Moderate road ride. Great for any fitness level. Some segments of this route may be unpaved and difficult to ride.
6
riders
21.1km
00:55
200m
200m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
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Good Coffee with great outside seating and plenty of room to put bikes.
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A song that—originally from the American gospel tradition—has traveled the world is a perfect fit for this church, which the parish has dedicated to the patron saint of All Saints. "Oh when the Saints go marching in, oh when the Saints go marching in, oh Lord, I want to be in that number, oh when the Saints go marching in." Over the decades, numerous versions of the lyrics have emerged, but an original text cannot be verified due to its early oral transmission. Many artists have taken up the gospel song and released their own interpretations, such as Bruce Springsteen with his session band at a concert in Dublin: https://www.youtube.com/watch?v=i6eKkirEcgE
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In quarter-hour film segments for a German-language television series, Tilmann Spengler introduces the lives and works of important writers and authors from all eras to culture-loving viewers. One of the women he honors as "classics of world literature" is the British author of "Pride and Prejudice" (to name her most famous work): * JANE AUSTEN (1775 to 1817). The segment (in German) can be found in the ARD Media Library at the following link =>> https://www.ardmediathek.de/video/klassiker-der-weltliteratur/jane-austen-stolz-und-vorurteil/ard-alpha/Y3JpZDovL2JyLmRlL3ZpZGVvL2NiOGJhYTI3LTkxYzMtNDRiNi05NjNlLTRlYzg2NDNmY2E5Ng
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Its worth the cycle just for the Moon Roast coffee. ☕
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The Yard is Café & Coffee shop with indoor and outdoor seating, serving Moon Roast coffee, toasties, salads, cakes, juices & more. Normal Opening Hours: Wednesday - Sunday 9am - 4pm
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There are 11 dedicated road cycling routes around Medstead, offering a variety of experiences for cyclists. These routes are highly rated by the komoot community, with an average score of 4.4 stars.
Road cycling around Medstead features a diverse landscape of rolling hills, woodlands, and picturesque country lanes, with many routes offering mostly paved surfaces. You'll find a mix of terrains, including sections within the South Downs National Park and areas like the "Hampshire Hangers," providing options for both leisurely rides and more challenging excursions.
Yes, Medstead offers 4 easy road cycling routes, perfect for beginners or those seeking a more relaxed ride. An example is the Bighton Church – Cafe Nosh loop from Four Marks, which is 13.1 miles (21.1 km) and typically takes less than an hour to complete.
Many routes incorporate stunning natural features. You can cycle through areas like Chawton Woods, along the River Itchen, or enjoy views from the South Downs National Park. Specific highlights include the Joan's Acre Wood, the Source of the River Itchen, and the Abbotstone Iron Age Fort and Nature Reserve, which offers excellent viewpoints.
Absolutely. Cycling routes can lead you past several interesting sites. You might encounter the heritage Watercress Line (Mid Hants Railway) or cycle near Avington Park and its lake. For those on longer rides, the historic Westgate in Winchester is also accessible. Nearby attractions include Jane Austen's House Museum and Alton Abbey.
The road cycling routes in Medstead are highly regarded by the komoot community, boasting an average rating of 4.4 out of 5 stars from over 40 reviews. Cyclists often praise the varied terrain, scenic country lanes, and the opportunity to explore both woodlands and rolling hills.
While there are no routes explicitly graded as 'difficult' in our current selection, the 7 moderate routes offer significant challenges with elevation gains and longer distances. For instance, the Longwood Dean Lane Tree Tunnel – Old Winchester Hill loop from Medstead covers 47.1 miles (75.8 km) and includes notable climbs.
Yes, many of the road cycling routes around Medstead are designed as loops, allowing you to start and finish in the same location. An example is the popular Moon Roast Café – Lovington Lane loop from Medstead, which is a moderate 29.2 miles (46.9 km) ride.
Yes, the Longwood Dean Lane Tree Tunnel – Old Winchester Hill loop from Medstead is known for its distinctive tree tunnel and offers views from Old Winchester Hill. Other routes may take you through Chawton Woods or along the River Itchen.
Medstead offers enjoyable road cycling throughout much of the year. Spring and autumn provide pleasant temperatures and beautiful scenery, with spring showcasing wildflowers like those in Bluebell Copse. Summer is also popular, though routes can be more exposed to the sun. Winter cycling is possible, but be prepared for cooler temperatures and potentially wet conditions.
For broader information on cycling opportunities across Hampshire, you can visit the Visit Hampshire website. Additionally, the South Downs National Park website provides details on cycling within the park, which borders Medstead.


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