4.5
(113)
1,102
riders
214
rides
Touring cycling routes around Maidstone, Kent, traverse a varied landscape characterized by the chalk ridges of the North Downs and the tranquil River Medway. The region offers a mix of gentle river paths, challenging hill climbs, and quiet country lanes. Cyclists can explore areas like the Greensand Ridge and the Weald, providing diverse terrain for all abilities.
Last updated: April 24, 2026
4.7
(3)
10
riders
42.0km
02:36
380m
380m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5.0
(1)
8
riders
56.5km
03:33
570m
570m
This difficult 35.1-mile touring cycling loop from Maidstone explores the Medway Estuary and Kent Downs, with 1870 feet of gain.

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4.5
(4)
29
riders
49.9km
02:54
170m
170m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
4.5
(4)
20
riders
33.6km
02:00
130m
130m
Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.
5.0
(12)
25
riders
18.5km
01:13
120m
120m
Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.
5.0
(2)
28
riders
30.0km
01:51
230m
230m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
4.7
(3)
23
riders
95.5km
05:44
710m
710m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
4.0
(1)
22
riders
Hard bike ride. Good fitness required. You may need to push your bike for some segments of this route.
5.0
(2)
23
riders
15.4km
01:03
60m
60m
Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.
5.0
(1)
16
riders
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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Newly opened independent bike shop with a good variety of bikes, parts, accessories and experienced bike mechanics. Located inside Lockmeadow Entertainment Centre.
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The Pilgrims way is an excellent long distance off road route, however due to it being a bronze age track way over a couple of thousand years some parts of it have become hollow ways and are essentially impassible or very heavy going in wet conditions, at worst it's only traversable by mountain bike in wet periods.
1
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The Dirty habbit at the foot of the climb provides refreshing hill accompaniments
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Stayed here for a night on my way from London to Folkestone. Very bike friendly, great food for dinner and breakfast. Highly recommend.
1
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This is NOT a path for the faint hearted! It's rough, very bumpy in parts, slippery when wet. I ride a hybrid - and it's not a path I would take again. It needs a specialist mountain bike.
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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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A nice easy and pleasing short bike ride along the river Medway
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Maidstone offers a diverse range of terrain for touring cyclists. You'll find tranquil, traffic-free paths along the River Medway, challenging hill climbs in the North Downs Area of Outstanding Natural Beauty (AONB) and the Greensand Ridge, and quiet country lanes through the Wealden countryside. The region's geography, often called the 'Garden of England,' also features scenic fruit orchards.
Yes, Maidstone has several easy routes. The River Medway towpath offers a gentle, traffic-free ride, perfect for families. For a specific route, consider the Frankies Farm Shop & Café – Oast Houses of Laddingford loop from Yalding, which is rated easy. Another accessible option is the View of the Canal Lock – The Old Boat loop from Maidstone East, which is also rated easy.
For more challenging rides, head to the North Downs AONB, where you'll encounter significant climbs around areas like Bluebell Hill, Boxley, Thurnham, and Hollingbourne. The Greensand Ridge and The Weald also offer demanding hill climbs through picturesque areas such as Linton and Sutton Valence. A difficult route to consider is The Medway Estuary loop from Maidstone, which features substantial elevation gain.
Maidstone's routes offer access to several points of interest. You can cycle past the historic Leeds Castle, often called 'the loveliest castle in the world.' The tranquil River Medway itself is a central feature, and you can also explore sections of the Pilgrims' Way. For natural beauty, the North Downs AONB provides spectacular views, and Mote Park offers a glorious lake and wildlife.
Yes, many routes in the area are designed as loops. For example, the Goudhurst loop from Yalding — High Weald is a popular circular route exploring the High Weald countryside. Another option is the Hampstead Road Lock – Lower Farm Road loop from Staplehurst, which takes you through the Kent countryside.
Yes, Maidstone is well-connected by public transport. Cyclists can take their bikes on Southeastern trains, though it's advisable to check for any restrictions during peak hours for non-folding bikes. This allows for flexibility, enabling you to start or end longer touring routes at various stations, particularly along the Paddock Wood line, such as Marden, Staplehurst, and Headcorn.
Yes, the Maidstone area is well-equipped with refreshment stops. The River Medway towpath features cafés, offering scenic spots to rest. Additionally, the Pilgrims Cycle Trail, which runs through the North Downs AONB, passes by charming local pubs, perfect for a break during your ride.
The area is highly rated by the komoot community, with an average score of 4.5 stars from over 100 reviews. Reviewers often praise the varied terrain, from tranquil river paths to challenging hill climbs, and the scenic beauty of the 'Garden of England' with its fruit orchards and historic landmarks.
The North Downs AONB, which skirts the outskirts of Maidstone, is renowned for its spectacular views. Areas like Bluebell Hill, Boxley, Thurnham, and Hollingbourne offer elevated perspectives. You can also find scenic viewpoints along routes that pass through the Greensand Ridge and The Weald. For a specific highlight, consider Hollingbourne Hill Climb for its panoramic outlooks.
There are over 200 touring cycling routes available around Maidstone, catering to various skill levels. This includes 67 easy routes, 114 moderate routes, and 36 difficult routes, ensuring options for every cyclist.
Maidstone offers enjoyable cycling throughout much of the year. Spring and summer provide pleasant weather for exploring the 'Garden of England' with its blooming orchards. Autumn brings beautiful foliage, especially in areas like the North Downs. While winter cycling is possible, be prepared for cooler temperatures and potentially muddier paths, particularly on unpaved sections.


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