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 9, 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

54.3km

03:22

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

4.5

(2)

riders

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

45.0km

02:47

420m

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

Su Westerman (CC BY-NC-ND 2.0)

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

Hiking Collection by

Aled Moses (CC BY-NC-SA 2.0)

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

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 ⛰️