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United Kingdom
England
South East England
Buckinghamshire

Sightseeing in Oxford loop via the Chiltern Hills

Moderate

26

riders

Sightseeing in Oxford loop via the Chiltern Hills

03:59

92.5km

660m

Road cycling

This moderate 57.5-mile road cycling loop from Oxford explores the challenging Chiltern Hills, offering historic sights and scenic landscape

Last updated: February 26, 2026

Tips

Your route passes through protected areas

Please check local regulations for:

Chiltern Hills AONB

New Marston Meadows

Waypoints

A

Start point

Bus stop

Get Directions

1

13.5 km

Chinnor Hill

Highlight (Segment) • Forest

Included in Simon Warren's guide to the best cycle climbs of the south east.

Tip by

2

38.0 km

Stanton St John Village

Highlight • Settlement

Beautiful village and impressive church

Tip by

3

47.4 km

The Handle Bar

Highlight • Restaurant

Fantastic coffee bar downstairs next to Bike Zone Oxford bike shop, plus a cafe upstairs. Fantastic brunches and great coffee, Magda was brilliant!

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4

48.3 km

Radcliffe Camera

Highlight • Historical Site

Famous library with dome

Translated by Google •

Tip by

5

74.4 km

Aston Hill Climb

Highlight (Segment) • Cycleway

This is a great long ascent/descent over nearly 3km.

Tip by

B

92.5 km

End point

Bus stop

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Way Types & Surfaces

Way Types

50.1 km

26.3 km

9.04 km

7.00 km

< 100 m

< 100 m

Surfaces

81.7 km

10.7 km

< 100 m

< 100 m

< 100 m

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Elevation

Elevation

Nothing selected – click and drag below to see the stats for a specific part of the route.

Highest point (250 m)

Lowest point (60 m)

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Weather

Powered by Foreca

Thursday 7 May

17°C

6°C

12 %

Additional weather tips

Max wind speed: 11.0 km/h

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This route was planned by komoot.

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Frequently Asked Questions

What is the overall difficulty and terrain like for this cycling loop?

This loop is rated as moderate, requiring good fitness. The terrain in the Chiltern Hills is notably hilly and undulating, featuring steep climbs and descents. While primarily on paved roads, be aware that some segments may be unpaved and challenging for road bikes with skinny tires, potentially requiring you to push your bike or find an alternative.

Where can I park to start this cycling route?

Since this is a loop starting and ending in Oxford, you'll want to find parking within or on the outskirts of the city. Consider public car parks in Oxford, or look for options that allow for longer stays suitable for a full day's ride. Specific parking details can vary, so it's best to check local Oxford parking information before your trip.

What are the best times of year to cycle this route?

The Chiltern Hills offer beautiful scenery year-round, but spring and autumn are generally ideal for cycling. In spring, you'll see wildflowers and lush greenery, while autumn brings stunning foliage. Summer can be pleasant, but be prepared for warmer temperatures. Winter cycling is possible, but check weather conditions for ice or heavy rain, which can make the hilly terrain more challenging.

Are there any permits or entrance fees required to cycle through the Chilterns National Landscape?

No, there are no specific permits or entrance fees required to cycle through the Chilterns National Landscape (formerly AONB). It's a protected landscape, but access for activities like cycling on public rights of way and designated routes is generally free. Always respect local signage and private land.

What interesting sights or landmarks will I see along the way?

This route combines the natural beauty of the Chilterns with historic Oxford. You'll pass through picturesque villages and enjoy rolling hills. Key highlights include the challenging Chinnor Hill, the charming Stanton St John Village, and the iconic Radcliffe Camera in Oxford. You'll also encounter the Aston Hill Climb, known to cyclists.

Is this cycling loop suitable for dogs?

This route is designed for racebikes and covers a significant distance on public roads and cycleways. While dogs are generally welcome in the Chilterns National Landscape, bringing a dog on a racebike loop of this nature is not typically recommended due to the speed, distance, and road conditions. If you wish to bring a dog, consider shorter, dedicated walking or family-friendly cycling trails where they can be safely accommodated.

Does this route connect with any other well-known cycling paths?

Yes, this loop incorporates sections of several other routes. Notably, it uses parts of the NCN National Route 57 and the Chilterns Cycleway. You may also briefly intersect with paths like the Barton-Menmarsh and Garsington-GreatMilton routes.

Are there places to stop for food and drink along the route?

Yes, the route passes through various villages and towns, offering opportunities for refreshments. In Oxford, you'll find numerous options, including The Handle Bar. As you cycle through the Chilterns, you'll encounter charming villages that often have pubs or cafes where you can refuel.

What kind of bike is best suited for this loop?

Given the route's classification as 'racebike' and its distance and elevation, a road bike is generally the most suitable. However, be aware that some sections may be unpaved or rutted, which can be challenging for very skinny tires. A road bike with slightly wider tires or a gravel bike might offer more comfort and versatility on these varied surfaces.

How long does it typically take to complete this cycling loop?

The estimated duration for this 92.5 km loop is approximately 4 hours. This is a moving time estimate and does not include stops for sightseeing, food, or rest. Your actual completion time will depend on your fitness level, speed, and how often you choose to pause and enjoy the scenery.

What should I bring for a day of cycling on this route?

For this moderate, nearly 100km racebike loop, essential items include a well-maintained road bike, helmet, appropriate cycling attire (including layers for changing weather), water bottles, snacks, a basic repair kit (spare tube, pump, tire levers), and a phone for navigation and emergencies. Don't forget sun protection and a small first-aid kit.

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