Explore the best cycling routes through and around Winchester, plus bike shops and bike cafés to visit
Grab your helmet, pump up those tyres and head off on two wheels along one of these Winchester cycle routes. There are loads of options for bike rides around Winchester, whether you're exploring Hampshire on a long-distance cycling holiday or after an easy cycle route to follow for an afternoon's bike ride.
There's glorious countryside to explore and lovely villages and market towns to discover, plus some serious hills to tackle. Don't forget to take a rest in one of Winchester's prettiest picnic spots, alfresco dining locations or characterful pubs.
Walking more your thing? Check out our guide to Walks in Winchester.
Curated by the Visit Winchester team.
Last updated: 9 June 2026.
National Cycle Network Route 23
This route runs from Reading to Southampton via Basingstoke, Alresford, Winchester and Eastleigh. The total route is around 86 miles, but you can break it down into smaller sections. It's all clearly signposted and you can find out more about it here.
Cycling from Winchester city centre? Part of Route 23, The Viaduct Way is 2.6 miles, begins at the Guildhall at the bottom of Winchester High Street and travels down to St Catherine’s Hill before continuing on to the lovingly restored Hockley Viaduct. Along the way you'll find Cadence Clubhouse café. You can return to the city on the Park & Ride bus or by following the same route back.
If you’d like a longer route, follow National Cycle Network Route 23 further south out of the city - the route runs parallel with walking route the Itchen Navigation Heritage Trail. The cycle path continues from the end of the viaduct way, through Shawford, Otterbourne, Eastleigh and beyond to Southampton. For more of an adventure, continue on the Red Squirrel Trail by catching the ferry to the Isle of Wight and cycling to the end of Route 23 at Sandown.
The South Downs Way
The South Downs Way is a 100-mile route, which starts in Winchester city centre and ends in Eastbourne. It's the only National Trail to lie entirely within a National Park and is accessible by foot, bike or horse! The long-distance trail follows the chalk downs and almost all of the route is off-road.
Looking for a shorter bike ride from Winchester city centre? The first section of The South Downs Way is Winchester to Exton and is around 12 miles. Starting at the cathedral, the route takes you out of the city, through the quaint village of Chilcomb. After Chilcomb you begin the first climb to Cheesefoot Head – a beautiful spot with spectacular views. The route then descends down into Exton.
King Alfred’s Way
If you're looking for an even longer adventure, the King Alfred's Way cycle route might be a good fit. The 220-mile off-road route officially begins at the Westgate Museum at the top of Winchester High Street. It will take you on a multi-day adventure, looping through the Anglo-Saxon kingdom of Alfred the Great, before bringing you back to the historic city of Winchester and ending at the iconic King Alfred Statue. You'll cycle past Stonehenge, Avebury stone circle, Iron Age hill forts, Farnham Castle, Salisbury Cathedral and more.
26-mile Winchester Circular
Pick up this cycle trail from outside Winchester Cathedral, before cycling out of the city and through the surrounding countryside. You'll whizz through Micheldever Woods and past the edge of pretty market town Alresford before picking up a section of the South Downs Way which will bring you back into the city to where you started.
Farley Mount Country Park Loop
A 14-mile cycle route, this loop takes you through some charming small villages on the outskirts of Winchester as well as past Crab Wood, West Wood and Parnholt Wood, through Farley Mount Country Park.
Cycling from Winchester city centre? Pick up the rural loop by cycling out of the city on Romsey Road and then Sarum Road.
Meon Valley Trail
Starting in West Meon and ending in the vibrant market town of Wickham, the Meon Valley Trail is a walking, riding and cycling route which follows the route of a disused railway line that once ran between Alton and Fareham. The 11-mile trail is picturesque and mainly flat, roughly following the route of precious chalk stream the River Meon.
More local Winchester city cycle routes
Cycle Winchester is a local cycling advocacy group for the Winchester area, aiming to make Winchester and its surrounding settlements ‘better by bike’. They organise an annual Mass Ride around Winchester city centre. Find out more about them and check out the cycle routes they recommend, tried and tested by local Winchester cyclists.
Hire a bike in Winchester
The Cycle Company in Shawford, near the train station, have everything you need for a day exploring Winchester by bicycle. All rentals include helmet, lock, puncture repair kit, charger, maps and advice and guidance on the best routes for your bike hire adventure. They rent out e-bikes for adults and regular bikes for children as well as child seats and ‘tag alongs’ for very little ones.
Cycle parking in Winchester city centre
If you’re in the city centre, there is plenty of culture, history, shopping, food and drink to be enjoyed – but where can you leave your bike? This handy map shows you to find cycle parking in Winchester city centre.
Cycle repair in Winchester city centre
If you need help with bike repairs, try EXO – the Winchester Bike Hub at Kings Walk in Winchester city centre. Bike shop Hoops on Easton Lane also has an on-site workshop for servicing and fixing bikes.
Bike cafés in Winchester
South Downs Social is a popular café and meeting place for those starting or ending their cycling adventures. You'll also find a selection of cycling lifestyle goods to browse, secure bike parking inside the café, live racing on two big screens and a calendar of cycling talks and events.
You'll find Cadence Clubhouse at the foot of St Catherine's Hill. It's a café serving hot food and drinks, that also offers an e-bike charging station, pump and basic tool station for quick fixes.
Walks in Winchester
Discover the best walks in Winchester, from self-guided city strolls to countryside hikes and…
Perfect picnic spots in Winchester
Discover characterful places for picnics in Winchester city and countryside
