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Routes
Road cycling routes
United Kingdom
England
South East England
Kent

Maidstone

The best road cycling routes around Maidstone

4.3

(91)

3,973

riders

577

rides

Road cycling routes around Maidstone offer diverse terrain across the "Garden of England," featuring rolling hills, river valleys, and sections of the North Downs. The region is characterized by its tranquil countryside, vineyards, and historic sites, providing varied environments for road cyclists. Routes often traverse the quiet lanes of The Weald and follow the River Medway, with opportunities for hill climbs along the Greensand Ridge. This landscape provides options for both leisurely rides and more challenging ascents.

Best road cycling…

Last updated: May 6, 2026

3.5

(4)

21

riders

#1.

Maidstone, Yalding and River Medway loop

57.3km

02:39

500m

500m

Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult 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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Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate

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

Moderate

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

Moderate

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

Easy

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

Moderate

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

Moderate

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
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Stour Valley Walk — Hike through Kent's finest scenery to the sea

Hiking Collection by

Dan Hobson

Tips from the Community

uɐʍoᴚ
February 14, 2025, Hollingbourne Hill Climb

The Dirty habbit at the foot of the climb provides refreshing hill accompaniments

1

0

One of my favourite climbs in the area (alongside Coldblow Land further west). From corner of Pilgrims Way it is 1km to the top. Becomes prgressivley steeper, the final ramp is around 20% gradient.

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Ignore the pubs and go here instead

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Beautiful views of the countryside.

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Brutal, brutal climb. Took the life out of me once you're 20%+. To make things worse, if you're wanting to stop, its difficult to do so as cars are coming up and down the road. I didn't stop but this isn't for the weak. However, it's largely 5-7 miles of descending afterwards and the climb is only extremely difficult for a short period.

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Great views if the weather is good

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1

It is not so common for a Christian place of worship – which encompasses the whole of heaven – to be dedicated to “ALL SAINTS”. Usually it is one (or occasionally two) named saints who hold the patronage of a church – and thus usually also of the parish or town in which it is located. But to find the origin of such a dedication, one has to go far back in history, because the model for this practice of dedication to ALL SAINTS can be seen as a pagan custom, according to which there were already central temples in pre-Christian times that were dedicated to all deities (PANTHEON). The probably most famous Pantheon, formerly a pagan temple and now a Christian place of worship, is located in the Italian capital.

Translated by Google

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Boxley Warren is a 83-hectare Local Nature Reserve north of Maidstone in Kent

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Frequently Asked Questions

What kind of terrain can I expect on road cycling routes around Maidstone?

Maidstone, situated in the 'Garden of England,' offers a varied landscape for road cyclists. You'll find rolling hills in The Weald, challenging ascents along the Greensand Ridge and sections of the North Downs, and tranquil, flatter paths along the River Medway. This diversity provides options for both leisurely rides and more strenuous climbs.

Are there any easy road cycling routes suitable for beginners or families in Maidstone?

Yes, Maidstone offers routes suitable for various skill levels. For an easier ride, consider the route to Leeds Castle Entrance Gate loop from Maidstone, which is approximately 12.7 miles (20.5 km) and has an easy difficulty grade. The Medway Towpath, while not a specific komoot route here, is also known for being a flat, traffic-free option ideal for families.

Where can I find challenging hill climbs for road cycling in the Maidstone area?

For those seeking a challenge, the North Downs and the Greensand Ridge, particularly around Linton, Sutton Valence, Hunton, and Yalding, offer excellent hill climbs. A notable route featuring a significant ascent is the Hollingbourne Hill Climb – Warren Lane Bluebell Forest loop from Otham, which includes over 600 meters of elevation gain.

What historical landmarks or natural features can I see while cycling around Maidstone?

The region is rich in historical sites and natural beauty. You can cycle past vineyards, historic villages, and natural reserves. Notable attractions include Leeds Castle, which can be reached via routes like the Leeds Castle Entrance Gate loop from Maidstone. Other points of interest include the Lenham Cross and the ruins of Sutton Valence Castle.

Are there any circular road cycling routes available near Maidstone?

Yes, many of the road cycling routes around Maidstone are designed as loops, allowing you to start and finish in the same location. Examples include the popular Maidstone, Yalding and River Medway loop, and the Vineyard Near Boxley – The King's Arms loop from Maidstone East.

What is the best time of year to go road cycling in Maidstone?

Maidstone is enjoyable for road cycling throughout much of the year. Spring and autumn offer pleasant temperatures and beautiful scenery, with spring bringing bluebells to forested areas and autumn showcasing vibrant foliage. Summer provides longer daylight hours, while winter rides are possible but may require more consideration for weather conditions.

How many road cycling routes are available in the Maidstone area on komoot?

There are over 590 road cycling routes available around Maidstone on komoot, catering to various distances and difficulty levels. This includes approximately 180 easy routes, 370 moderate routes, and 37 difficult routes for more experienced cyclists.

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

The road cycling routes in Maidstone are highly rated by the komoot community, with an average score of 4.3 stars from over 80 reviews. Cyclists often praise the tranquil countryside, the varied terrain offering both riverside paths and challenging climbs, and the scenic beauty of the 'Garden of England'.

Can I find routes that pass through vineyards or offer views of the Kent countryside?

Absolutely. The Maidstone area is known for its picturesque vineyards and expansive countryside views. Routes like the Vineyard Near Boxley – The King's Arms loop from Maidstone East specifically traverse vineyard landscapes. Many other routes, such as the View of the Kent Countryside – Hever Castle & Gardens loop from Wateringbury, offer stunning vistas of the rolling Kentish hills.

Are there any specific parks or traffic-free areas suitable for cycling in Maidstone?

Mote Park in Maidstone is a large park offering family-friendly, traffic-free cycling paths. It's a great spot for practicing cycling skills or enjoying a relaxed ride away from roads. Additionally, the Medway Towpath provides a tranquil, traffic-free green corridor along the River Medway.

How can I get to the cycling routes in Maidstone using public transport?

Maidstone is well-connected by public transport, making it accessible for cyclists. Maidstone East and Maidstone Barracks are central train stations, and many routes, such as the Vineyard Near Boxley – The King's Arms loop from Maidstone East, start directly from these areas. Check local train and bus services for specific routes and bike carriage policies.

Where can I find parking for road cycling routes in Maidstone?

Parking is available in and around Maidstone, often near town centers or designated trailheads. For routes starting from specific villages or attractions, check local parking facilities. Mote Park also offers parking for visitors. Always verify parking availability and restrictions before your ride.

Are there any long-distance road cycling routes or tours that start from Maidstone?

While many routes are day trips, Maidstone's location allows for longer tours connecting to iconic paths like sections of the North Downs Way or the Pilgrims' Way. For a longer moderate ride, consider the Catts Hill Climb – The Ferry Inn loop from Marden, which covers over 68 miles (109 km).

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