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.
Last updated: May 6, 2026
3.5
(4)
21
riders
57.3km
02:39
500m
500m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
4.3
(3)
53
riders
55.6km
02:38
610m
610m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

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5.0
(2)
48
riders
51.2km
02:13
460m
460m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
5.0
(1)
55
riders
110km
04:50
890m
890m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
4.7
(3)
43
riders
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
4.0
(1)
48
riders
20.5km
00:55
190m
190m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
4.0
(2)
35
riders
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
42
riders
62.4km
02:48
290m
290m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
4.5
(2)
37
riders
25.5km
01:16
250m
250m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
5.0
(1)
33
riders
52.8km
02:28
530m
530m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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The Dirty habbit at the foot of the climb provides refreshing hill accompaniments
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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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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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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.
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Boxley Warren is a 83-hectare Local Nature Reserve north of Maidstone in Kent
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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.
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.
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.
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.
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.
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.
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.
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'.
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.
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.
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.
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.
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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