4.3
(11)
587
riders
7
rides
No traffic road cycling routes around Gerrards Cross are situated in an area characterized by rolling chalk hills, ancient woodlands, and well-surfaced tracks. The region offers diverse landscapes, including the Chiltern Hills Area of Outstanding Natural Beauty, Black Park Country Park, and Burnham Beeches. These areas provide a network of paved surfaces and minor roads, many of which are closed to cars, making them suitable for road cycling.
Last updated: July 15, 2026
92
riders
103km
05:14
1,090m
1,090m
Hard road ride. Very good fitness required. Some segments of this route may be unpaved and difficult to ride.
8
riders
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

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2.0
(1)
7
riders
31.6km
01:29
180m
180m
Moderate road ride. Great for any fitness level. Some segments of this route may be unpaved and difficult to ride.
5.0
(1)
6
riders
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
5.0
(1)
20
riders
53.2km
02:37
440m
440m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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Popular around Gerrards Cross
Truly a village that is steeped in olde worlde charm. Some great restaurants and pubs. The history seeps through its pores. The Kings Arms Hotel & The Crown Hotel & Pub in Amersham, was the set of a scene the 4 Weddings and a funeral movie.
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In the summer there are tours for Β£3 donation from 2pm on Sunday
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Chenies climb is a hard climb and if you like climbing you will probably do it easily
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Beautiful town and perfect to finish off hike/ walking trail, great choice of CafΓ©, try sitting outside @ Amersham House for coffee/ brunch
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Winchmore Hill goes back to the 12th century: there used to be a small settlement here supporting farms grouped around a Common and a pond (those were the days). In 1958, the pond was filled in, but luckily the Common is still here, on the edge of what used to be Wycombe Heath: 4,000 acres of open common land providing grazing for animals and material for firewood. It's a lovely hamlet. There is a great information board, from which you can learn more about the history of the place. And a good pub in a village can never be wrong! - so make sure you make a stop at The Plough!
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As English villages in the Chiltern Hills go, this one is one of the most attractive. This is the kind of place I tend to think of when I read Agatha Christie's Miss Marple. The village name is Anglo-Saxon and means "a woodland clearing". Another little fun fact: Sir Arthur Lasenby Liberty (1843β1917), proprietor of the famous Regent Street (London) store, Liberty & Co., lived here and built a Manor house here in 1900. He was associated with the Art Nouveau style.
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Jack & Alice is a neighbourhood restaurant and bar in the heart of the local community, serving breakfast, lunch and dinner. A family business and work with the best local suppliers to deliver high-quality food and drinks for our guests to enjoy. Located in the centre of Gerrards Cross, close to the train station and the cinema, weβre the perfect place for everything from breakfast through to a celebratory evening meal. Serving classic cocktails and a wonderfully curated wine list, and open daily until 11 p.m.
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There are 7 dedicated no traffic road cycling routes around Gerrards Cross featured in this guide. These routes cater to various fitness levels, including easy, moderate, and difficult options.
Yes, for an easier ride, consider the Up Corner, Chalfont St Giles β Chalfont St Giles Country Lane loop from Gerrards Cross. This route is approximately 19.4 km long with a modest elevation gain, making it a great option for those looking for a less strenuous, car-free experience.
The routes around Gerrards Cross take you through the beautiful South Bucks and Chiltern Hills. You'll experience rolling chalk hills, ancient woodlands, and charming villages. Many routes utilize minor roads or dedicated paths, offering a serene cycling experience away from heavy traffic.
Yes, all the routes listed in this guide are circular loops starting and ending near Gerrards Cross. For example, the challenging Bryants Bottom Road β Penn Village loop from Gerrards Cross is a long circular route covering over 100 km.
Many routes in the Chilterns pass through picturesque villages and market towns, offering opportunities to stop at country pubs and cafes. While specific stops aren't detailed for every route, areas like Old Amersham, which is part of the Chenies Climb and Village β Old Amersham Town Centre loop, are known for their amenities.
You can encounter several interesting spots. The Harehatch Lane β Burnham Beeches loop takes you near Burnham Beeches, a National Nature Reserve known for its ancient woodland. Other nearby attractions include the historic Old Amersham Town Centre, Black Park, and Ruislip Lido.
The komoot community highly rates the cycling experience around Gerrards Cross, with an average score of 4.5 out of 5 stars from 13 ratings. Cyclists often praise the quiet roads and the beautiful, varied terrain of the Chilterns.
Absolutely. For experienced cyclists seeking a longer, challenging ride with minimal traffic, the Bryants Bottom Road β Penn Village loop from Gerrards Cross covers over 100 km with significant elevation, offering a demanding yet rewarding experience.
Spring and autumn generally offer the most pleasant conditions for road cycling in the region, with milder temperatures and beautiful scenery. Summer can also be excellent, though it's wise to start earlier to avoid the warmest part of the day. Winter cycling is possible but be prepared for colder, potentially wetter weather.
While not directly on all routes, the region has several beautiful water features. The Ruislip Lido and Shardeloes Lake are notable lakes in the wider area, and some routes might offer glimpses of smaller ponds or streams, such as the Village Green and Pond in Chalfont St Giles.
Gerrards Cross has a train station with connections, making it a potential starting point for routes. However, specific public transport access points for each route are not detailed here. It's recommended to check local transport links to the starting points of your chosen routes.
While specific parking information for each route isn't provided, Gerrards Cross itself has parking facilities. For routes venturing into areas like Black Park or Burnham Beeches, dedicated car parks are usually available at these country parks, often with a fee. Always check local parking regulations before you arrive.


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