Routes

Planner

Features

Updates

App

Get the App

Medway

Medway

The best cycling routes in Medway

4.5

(134)

1,578

riders

161

rides

Cycling in Medway is one of the most enjoyable ways to explore more of this part of South East England. So you can find your perfect Medway bike ride, we’ve reviewed our full collection of cycling routes in the region to deliver the best. Just click on each route to see a full breakdown of detailed information including elevation profiles and surface analyses, and browse real tips and photos uploaded by other members of the komoot community.

Last updated: October 15, 2025

4.5

(10)

riders

1. The Hoo Peninsula loop from Rochester

34.3km

02:07

230m

Intermediate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Navigate

Send to Phone

Save

Intermediate

3.3

(11)

128

riders

2. View of Rochester Cathedral – Cooling Castle Gatehouse loop from Chatham

52.4km

03:11

360m

Intermediate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Navigate

Send to Phone

Save

Intermediate

Let us show you the way with the komoot mobile app

With a free komoot account, you can easily find, customize, and navigate endless outdoor adventures in England and beyond.

4.0

(2)

riders

3. No. 2 Basin, Chatham Dockside – View of Sheppey Crossing loop from Chatham

47.3km

02:53

320m

Intermediate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Navigate

Send to Phone

Save

Intermediate

5.0

(5)

riders

4. Seafront View – View of Sheppey Crossing loop from Rainham

49.4km

03:02

230m

Intermediate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Navigate

Send to Phone

Save

Intermediate

5.0

(6)

riders

5. St. Mary's Island – Horrid Hill loop from Gillingham

26.4km

01:41

140m

Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.

Navigate

Send to Phone

Save

Easy

5.0

(1)

riders

6. Horrid Hill – Bredgar Farm Shop & Tea Room loop from Gillingham

53.7km

03:19

370m

Intermediate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Navigate

Send to Phone

Save

Intermediate

3.3

(8)

riders

7. Higham Lakes – Thames and Medway Canal Path loop from Wainscott

22.5km

01:21

90m

Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.

Navigate

Send to Phone

Save

Easy

4.7

(3)

riders

8. Milstead Manor – Bredgar Farm Shop & Tea Room loop from Parkwood

43.4km

02:41

390m

Intermediate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Navigate

Send to Phone

Save

Intermediate

5.0

(1)

riders

9. Horrid Hill – St. Mary's Island loop from St. Marys Island

23.8km

01:28

80m

Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.

Navigate

Send to Phone

Save

Easy

riders

10. Pilgrims Way – Hollingbourne Hill Climb loop from Chatham

56.2km

03:33

610m

Expert bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Navigate

Send to Phone

Save

Expert

Get access to more routes and recommendations from other explorers.

Already have an account?

Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.

Other adventures in Medway

A historic hike along breathaking coastline — Saxon Shore Way

Hiking Collection by

Dan Hobson

Hike through 3,000 years of heavenly history — North Downs Way

Hiking Collection by

Kit P

Walk Britain – 90 car-free adventures in England, Wales and Scotland

Hiking Collection by

elisedowning

Most popular routes in Medway

Hiking in Medway

Road Cycling Routes in Medway

Running Trails in Medway

Easy hikes in Medway

MTB Trails in Medway

Gravel biking in Medway

Most popular attractions in Medway

Places to see

Castles

Get inspired with the komoot mobile app

With a free komoot account, you can easily find, customize, and navigate endless outdoor adventures around London and beyond.

Join komoot Now

Didn’t find what you were looking for?

Check out more Cycling routes throughout Medway below and find the perfect route in your destination.

Isle Of Grain Halling Cuxton Cooling Stoke Allhallows Frindsbury Extra Great Chattenden Wood St Mary Hoo High Halstow National Nature Reserve High Halstow Cliffe And Cliffe Woods Hoo St. Werburgh

Explore more

Browse the best Cycling routes in other regions.

Hampshire Kent Surrey West Sussex East Sussex Oxfordshire Isle of Wight Canterbury Brighton and Hove Buckinghamshire Southampton Milton Keynes North Wessex Downs Aonb Hackington Northwood Berkshire Harbledown And Rough Common Blean Windsor and Maidenhead Portsmouth Bracknell Lake Reading Chislet Wokingham East Cowes Ryde Newport Slough Little Brickhill Speen Wokingham Shanklin Gurnard Shaw Cum Donnington Cowes Newbury Bradwell Central Milton Keynes Ventnor Shalfleet Tilehurst Yarmouth Freshwater Fishbourne Woodley East Garston Wroxall Great Shefford Haversham-Cum-Little Linford Bow Brickhill Remenham Earley St Nicholas, Hurst Bletchley And Fenny Stratford Hungerford Farnborough Wexham Court Purley On Thames Wootton Bridge Loughton and Great Holm Castlethorpe Simpson And Ashland Winterbourne Arborfield And Newland Walton Fawley Lower Hardres and Nackington Charvil Barham Thanington Newchurch Sandown West Bletchley Womenswold Chicheley Arreton Sherington Brading Stantonbury Chaddleworth Havenstreet And Ashey Kents Hill, Monkston And Brinklow Totland Twyford Greenham New Bradwell Ruscombe Lathbury Newport Pagnell Kingston Chillerton And Gatcombe Wolverton And Greenleys Gayhurst Wokingham Without Bembridge Basildon Wavendon Hoath Finchampstead Chestfield Holybrook Great Linford Old Woughton Thatcham Bridge Rottingdean Sulham Whippingham Sulhamstead Stoke Goldington Brighstone Ickham And Well Littlebourne Winnersh Nettlestone And Seaview Hanslope Englefield Brightwalton Bekesbourne With Patrixbourne Rookley Moulsoe Theale Godshill Woburn Sands Aldermaston Chartham Britwell Streatley Shorwell Cold Ash Chale Shinfield Niton And Whitwell Woughton On The Green Cold Brayfield Swallowfield Calverton Fairfields Stony Stratford Colnbrook With Poyle Tidmarsh Petham Beech Hill Shenley Church End Pangbourne Bishopsbourne Wokefield Adisham Wasing Shenley Brook End Westbere Sturry Wargrave Bucklebury Sonning Tyringham And Filgrave North Crawley Astwood Catmore Woolhampton East Ilsley Ufton Nervet West Ilsley Fordwich Enborne Upper Hardres Frilsham Burghfield Chieveley Brimpton Lambourn Aldworth Waltham Yattendon Calbourne Beenham Beedon Campbell Park Hermitage Hampstead Norreys Ashampstead Clifton Reynes Padworth Leckhampstead West Woodhay Peasemore Combe Ravenstone Abbey Hill Hampstead Marshall Boxford Barkham Hardmead Wickhambreaux Compton Midgham Stanford Dingley Warrington Herne And Broomfield Weston Underwood St. Helens Welford Stratfield Mortimer Whitehouse Kintbury Inkpen Lavendon Emberton Olney Newton Blossomville

The best cycling routes in Medway

1. The Hoo Peninsula loop from Rochester

2. View of Rochester Cathedral – Cooling Castle Gatehouse loop from Chatham

3. No. 2 Basin, Chatham Dockside – View of Sheppey Crossing loop from Chatham

4. Seafront View – View of Sheppey Crossing loop from Rainham

5. St. Mary's Island – Horrid Hill loop from Gillingham

6. Horrid Hill – Bredgar Farm Shop & Tea Room loop from Gillingham

7. Higham Lakes – Thames and Medway Canal Path loop from Wainscott

8. Milstead Manor – Bredgar Farm Shop & Tea Room loop from Parkwood

9. Horrid Hill – St. Mary's Island loop from St. Marys Island

10. Pilgrims Way – Hollingbourne Hill Climb loop from Chatham

Other adventures in Medway

Most popular routes in Medway

Most popular attractions in Medway

Get inspired with the komoot mobile app

Didn’t find what you were looking for?

Explore more

Get ready to conquer new peaks

We value your privacy ⛰️

We value your privacy ⛰️