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United Kingdom
England
South East England
Oxfordshire

Chiltern Hills loop from Oxford

Hard

4.0

(1)

3

riders

Chiltern Hills loop from Oxford

05:10

80.4km

700m

Cycling

This difficult 50.0-mile touring cycling loop from Oxford explores the Chilterns National Landscape, featuring challenging climbs and scenic

Last updated: February 26, 2026

Tips

Your route passes through protected areas

Please check local regulations for:

Chiltern Hills AONB

Waypoints

A

Start point

Bus stop

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1

28.4 km

View from Watlington Kicker

Highlight (Segment) • Viewpoint

Certainly a testing climb as you enter the Chiltern Hills, but the view and this wildlife at the top are well worth it.

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2

35.3 km

Great cyclists cafe, free water tap to refill bottles. V popular with local cyclists and a walkers.

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3

41.1 km

All Saints' Church, Fawley

Highlight • Religious Site

The current building dates from the twelfth century and appears to been built over two periods, 1170–1210 and 1300–1340.

There is reference to an earlier church, likely to be on …

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4

53.1 km

The road takes you through sprawling fields of wildflowers and crops, adding bursts of colour to the landscape hills. This is a fantastic road for cycling, with spectacular views a plenty!

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5

75.0 km

Thames Path

Highlight (Segment) • Trail

The path is shared with walkers and is not massively wide, so caution and respect are required. Absolutely beautiful scenery though and the surface is very good as well.

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B

80.4 km

End point

Bus stop

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Way Types & Surfaces

Way Types

49.4 km

16.7 km

5.54 km

3.89 km

3.07 km

1.59 km

333 m

Surfaces

48.2 km

25.4 km

5.70 km

684 m

530 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 (240 m)

Lowest point (50 m)

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Weather

Powered by Foreca

Thursday 7 May

17°C

7°C

20 %

Additional weather tips

Max wind speed: 15.0 km/h

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This route was planned by komoot.

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Frequently Asked Questions

How challenging is the Chiltern Hills loop from Oxford?

This cycling loop is rated as difficult. It covers a distance of approximately 80.4 km with a significant elevation gain of around 700 meters. You should have good to very good fitness to comfortably complete it, as it features numerous steep climbs and descents characteristic of the Chiltern Hills.

What kind of terrain will I encounter on this route?

The terrain is distinctly undulating with a mix of surfaces. You can expect mostly paved roads, including asphalt and other paved surfaces, but also sections of cycleways and state roads. Some parts may include unpaved paths or compacted gravel, especially on routes within the Chilterns, which can be challenging.

What are the main points of interest along the way?

The route offers spectacular scenery and several notable points of interest. You'll pass through green hills, ancient woodlands, and charming villages. Highlights include the expansive View from Watlington Kicker, the picturesque View of the Rolling Hills and Wildflower Fields in Chilterns National Landscape, and the historic All Saints' Church, Fawley. You'll also encounter sections of the beautiful Thames Path.

When is the best time of year to cycle this loop?

The Chiltern Hills are beautiful year-round, but spring and summer (April to September) generally offer the most pleasant cycling conditions with warmer weather and blooming wildflowers. Autumn provides stunning foliage. Chalk trails, common in the Chilterns, drain well in dry conditions but can become slippery when wet, so consider this during wetter seasons.

Are there places to stop for refreshments along the route?

Yes, there are charming villages and spots where you can refuel. A popular stop is The Barn at Turville Heath Café, which is known for being cyclist-friendly and often has a free water tap for refilling bottles. You'll find other pubs and cafes in the villages you pass through.

Where can I park to start this cycling loop from Oxford?

As the loop starts and ends in Oxford, you can look for public parking facilities within or on the outskirts of the city. Consider parking at one of Oxford's Park & Ride sites and cycling into the city center to begin your route, which can be a convenient option for longer tours.

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

Yes, this route incorporates sections of several other well-known paths. Notably, it includes parts of the Chilterns Cycleway (12% of the route), Shakespeare's Way (12%), and NCN National Route 57 (10%). You'll also briefly join the Thames Path (8%) and The Chiltern Way (10%).

Is this cycling route dog-friendly?

While the route primarily follows roads and established cycleways, which are generally fine for dogs in a trailer or basket, some sections might include unpaved paths or bridleways. If you plan to bring a dog, ensure they are comfortable with cycling alongside or in a carrier, and always keep them on a leash when off-road or near livestock.

Do I need any permits or pay entrance fees for the Chilterns National Landscape?

No, there are no specific permits or entrance fees required to cycle through the Chilterns National Landscape (formerly an Area of Outstanding Natural Beauty). The area is open for public access, but please respect private land, follow the Countryside Code, and leave no trace.

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

This loop is estimated to take approximately 5 hours and 10 minutes of active cycling time. However, this duration can vary significantly based on your fitness level, the number and length of stops you make for refreshments or sightseeing, and weather conditions. Plan for a full day out to enjoy it thoroughly.

Are there any specific challenging climbs I should be aware of?

The Chiltern Hills are known for their 'punchy' and steep climbs. While specific named climbs like Chinnor Hill or Aston Hill Climb might be on other routes, you can expect numerous challenging ascents throughout this loop. Pacing yourself and being prepared for significant elevation changes is key to enjoying the ride.

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